Verfügbarkeit: Catalytic oxidation in organic synthesis

Catalytic oxidation in organic synthesis:

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Bibliographische Detailangaben
Weitere Verfasser:	Muniz, Kilian (HerausgeberIn)
Format:	Buch
Sprache:	English
Veröffentlicht:	Stuttgart Thieme 2018
Schriftenreihe:	Science of synthesis 2017, 4 Science of synthesis reference library
Schlagworte:	Organische Synthese Katalytische Oxidation Organic Chemistry Organic Synthesis Organic Reactions Organic Transformations Review Referenzwerk Organische Chemie Catalysis Green Chemistry Oxidation Organocatalysis Photocatalysis Epoxidation Dihydroxylation Wacker Process Biomimetic Oxidation Asymmetric Catalysis Chemie Aufsatzsammlung
Online-Zugang:	Inhaltsverzeichnis Inhaltsverzeichnis
Beschreibung:	XXXIX, 838 Seiten Illustrationen
ISBN:	9783132012417 3132012319

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653			\|a Organic Reactions
653			\|a Organic Transformations
653			\|a Review
653			\|a Referenzwerk
653			\|a Organische Chemie
653			\|a Catalysis
653			\|a Green Chemistry
653			\|a Oxidation
653			\|a Organocatalysis
653			\|a Photocatalysis
653			\|a Epoxidation
653			\|a Dihydroxylation
653			\|a Wacker Process
653			\|a Biomimetic Oxidation
653			\|a Asymmetric Catalysis
653			\|a Chemie
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Datensatz im Suchindex

_version_	1804178171738718208
adam_text	CATALYTIC OXIDATION IN ORGANIC SYNTHESIS PREFACE ............................................................................................................... V VOLUME EDITORS PREFACE ................................................................................ IX ABSTRACTS ................................................. XI TABLE OF CONTENTS ........................................................................................ XXV 1 INTRODUCTION K. MUNIZ ............................................................................................................. 1 2 GENERAL CONCEPTS IN CATALYTIC OXIDATION .......................................................... 7 2.1 PHOTOCATALYTIC OXIDATION A. G. GRIESBECK, S. SILLNER, AND M. KLECZKA ............................................................ 7 2.2 CATALYTIC OXIDATIONS WITH HYPERVALENT IODINE F. V. SINGH AND T. WIRTH ....................................................................................... 29 2.3 WATER AS AN OXYGEN SOURCE FOR OXIDATION REACTIONS P. GARRIDO-BARROS, I. FUNES-ARDOIZ, P. FARRAES, C. GIMBERT-SURINACH, F. MASERAS, AND A. LLOBET ....................................................................................................... 63 2.4 DEHYDROGENATION Y. KAYAKI AND T. IKARIYA ........................................................................................ 81 2.5 BIOMIMETIC OXIDATION IN ORGANIC SYNTHESIS L VICENS, M. BORRELL, AND M. COSTAS .................................................................. 113 3 METAL-CATALYZED OXIDATION OF ALKANES TO GIVE ESTERS OR AMINES A. CABALLERO, M. M. DIAZ-REQUEJO, AND P. J. PEREZ ............................................ 155 4 ALLYLIC, BENZYLIC, AND PROPARGYLIC OXIDATION P. CHEN AND G. LIU ................................................ 101 5 OXIDATION OF ALKENES ..................................... 245 5.1 EPOXIDATION OF ALKENES A. BERKESSEL, H. ENGLER, AND T. M. LEUTHER ...................... .................................. 245 5.2 DIOXYGENATION OF ALKENES C. MARTINEZ AND K. MUNIZ ................................................................................. 309 5.3 AMINOHYDROXYLATION AND AMINOOXYGENATION OF ALKENES S. R. CHEMLER AND T. WDOWIK ............................................................................ 343 5.4 HALOGENATION AND HALOCYDIZATION OF ALKENES A. ANDRIES-ULMER AND T. GULDEN .......................................................................... 389 5.5 THE WACKER PROCESS N. J. RACE, H. H. PATEL, AND M. S. SIGMAN ........................................................... 429 6 SULFINYL- AND SULFONYL-CONTAINING DIRECTING GROUPS IN CH OXIDATION OF ARENES R. GOEMEZ-ARRAYAS AND N. RODRIGUEZ ................................................................. 449 7 GOLD-CATALYZED OXIDATION OF ALKYNES P. CALLEJA, R. DOREL, AND A. M. ECHAVARREN ........................................................... 479 8 OXIDATION OF ALCOHOLS ........................................................................................ 529 8.1 RECENT DEVELOPMENTS IN CATALYTIC ALCOHOL OXIDATION USING NITROXYL RADICALS L. M. VORNAN, N. L. HUGHES, AND M. J. MULDOON ................................................ 529 8.2 ENANTIOSELECTIVE OXIDATION OF ALCOHOLS B. M. STOLTZ, A. C. WRIGHT, D. C. EBNER, AND N. PARK ........................................... 569 9 CATALYTIC AEROBIC OXIDATION OF PHENOLS J.-P. LUMB AND K. V. N. ESGUERRA ........................................................................ 587 10 -OXIDATION OF CARBONYL COMPOUNDS M. UYANIK AND K. ISHIHARA ................................................................................... 635 11 OXIDATION OF AMINES AND IM-HETARENES N. JIAO AND Z. LI .................................................................................................... 671 12 AEROBIC OXIDATIVE INTERMOLECULAR CROSS-COUPLING AND HECK REACTIONS F. BEILINA AND L A. PEREGO ................................................... 721 KEYWORD INDEX .................................................................................................. 767 AUTHOR INDEX ..................................................................................................... 797 ABBREVIATIONS 833 2 2.1 2.1 2.1.1 2.1.1.1 2.1.1.1.1 2.1.1.1.2 2.1.1.1.3 2.1.1.2 2.1.1.3 2.1.2 2.1.2.1 2.1.2.2 2.1.23 2.1.2.4 2.1.2 5 2.1.3 2.1.3.1 2.1.32 2.1.33 2.1.3.4 2.1.4 TABLE OF CONTENTS INTRODUCTION K. MUNIZ INTRODUCTION .......................................................... . ............................................ 1 GENERAL CONCEPTS IN CATALYTIC OXIDATION PHOTOCATALYTIC OXIDATION A. G. GRIESBECK, S. SILLNER, AND M. KLECZKA PHOTOCATALYTIC OXIDATION ......................................................................... TRIPLET OXYGEN TRAPPING OF PHOTOGENERATED RADICALS ................................ TRAPPING OF MONORADICALS ........................................................................... RADICAL ADDITION TO ALKENES TO GENERATE CARBON RADICALS ........................ HYDROGEN ABSTRACTION TO GENERATE CARBON RADICALS ................................. DEPROTONATION OF RADICAL CATIONS TO GENERATE CARBON RADICALS .............. TRAPPING OF RADICAL CATIONS ............................................ ........................... TRAPPING OF BIRADICALS .................................................................................. PHOTOCHEMICAL SUPEROXIDE GENERATION AND REACTIONS ............................... AROMATIC HYDROXYLATION VIA ARYLBORONATES ................................................ BENZYLIC OXIDATION VIA ACRIDINIUM PHOTOCATALYSIS ...................................... BENZYLIC ACTIVATION BY ELECTRON-TRANSFER-INITIATED CH BOND CLEAVAGE AND RADICAL TRAPPING WITH SUPEROXIDE ............................................................... BENZYLIC ACTIVATION BY ELECTRON-TRANSFER-INITIATED CC BOND CLEAVAGE AND RADICAL TRAPPING WITH SUPEROXIDE ............................................................... BENZYLIC ACTIVATION BY ELECTRON TRANSFER AND RADICAL CATION TRAPPING WITH SUPEROXIDE ....... .................................................................................. PHOTOCHEMICAL SINGLET OXYGEN GENERATION AND REACTION * . ....................... SINGLET OXYGEN ENE REACTIONS .................................................................... SINGLET OXYGEN [4 + 2]-CYCLOADDITION REACTIONS ......................................... SINGLET OXYGEN [2 + 2]-CYCLOADDITION REACTIONS ......................................... SINGLET OXYGEN HETEROATOM OXIDATION . ...................................................... MISCELLANEOUS PHOTOOXIDATION PROCESSES ................................................... 7 8 9 9 10 10 11 12 13 13 14 14 15 15 17 18 20 22 23 23 2.2 CATALYTIC OXIDATIONS WITH HYPERVALENT IODINE F. V. SINGH AND T. WIRTH 2.2 CATALYTIC OXIDATIONS WITH HYPERVALENT IODINE ................................................ 29 2.2.1 OXIDATION REACTIONS USING LODOARENES AS PRECATALYSTS ...................................... 29 2 . 2 . 1 .1 LODINE(LLL)-CATALYZED OXIDATION REACTIONS ........................................................... 29 2 . 2 . 1 . 1.1 LODINE(LLL)-CATALYZED OXIDATION OF ALCOHOLS .......................................................... 29 2 . 2.1 . 1.2 LODINE(LLL)-CATALYZED OXIDATION OF PHENOLS ........................................................... 32 2.2.1.1.2.1 LODINE(LLL)-CATALYZED OXIDATION OF PHENOLS WITHOUT CYCLIZATION ........................... 32 2 . 2.1 . 1 . 2.2 LODINE(LLL)-CATALYZED OXIDATION OF PHENOLS WITH CYCLIZATION ................................ 35 2 . 2 . 1 .1.3 LODINE(LLL)-CATALYZED OXIDATION OF ALKYLARENES ..................................................... 40 2.2.11.4 LODINE(LLL)-CATALYZED OXIDATION OF ALKENES AND ALKYNES ....................................... 41 2 . 2.12 LODINE(V)-CATALYZED OXIDATION REACTIONS ............................................................. 44 2.2.12.1 LODINE(V)-CATALYZED OXIDATION OF ALCOHOLS ......................................................... 45 2.2.12.11 1-HYDROXY-1,2-BENZIODOXOL-3(1H)-ONE 1-OXIDE CATALYZED OXIDATION OF ALCOHOLS 45 2.2.12.12 2-LODYLBENZENESULFONIC ACID CATALYZED OXIDATION OF ALCOHOLS .......................... 49 2.2.12.13 LODYLBENZENE-CATALYZED OXIDATION OF ALCOHOLS .................................................. 50 2 . 2 . 12.2 LODINE(V)-CATALYZED OXIDATION OF PHENOLS ........................................................... 53 2.2.12.3 LODINE(V)-CATALYZED OXIDATION OF ALKYLARENES ..................................................... 54 2.2.13 HYPERVALENT IODINE CATALYZED ENANTIOSELECTIVE OXIDATION REACTIONS ................ 57 2.3 WATER AS AN OXYGEN SOURCE FOR OXIDATION REACTIONS P. GARRIDO-BARROS, I. FUNES-ARDOIZ, P. FARRAES, C. GIMBERT-SURINACH, F. MASERAS, AND A. HOEBET 2.3 WATER AS AN OXYGEN SOURCE FOR OXIDATION REACTIONS .................................... 63 2.3.1 PRELIMINARY CONSIDERATIONS .................................................................................. 65 2 . 3.2 CASE STUDIES ON THE USE OF WATER AS AN OXYGEN SOURCE .................................... 67 2 . 3 . 2.1 ORGANIC SUBSTRATE OXIDATION REACTIONS WITH WATER AND LIGHT USING A MANGANESE PORPHYRIN COMPLEX AS CATALYST ..................................................... 67 2 . 3 . 2.2 PHOTOCATALYTIC OXIDATION OF SULFIDES AND BENZYLIC ALCOHOLS USING WATER, OXORUTHENIUM(IV)-BASED CATALYSTS, AND BISMUTH VANADATE ................... 70 2 . 3.23 OXIDATION OF ALCOHOLS TO CARBOXYLIC ACIDS USING WATER AS THE OXYGEN SOURCE: A ONE-POT PROCESS WITH A RUTHENIUM PINCER COMPLEX ....................................... 72 2.3.3 INTEGRAL PHOTOELECTROCHEMICAL CELLS ................................................................... 74 2.3.4 CONCLUSIONS .......................................................................................................... 77 2.4 DEHYDROGENATION Y. KAYAKI AND T. IKARIYA 2.4 DEHYDROGENATION ............................................... 81 2.4.1 TRANSFER DEHYDROGENATION OF ALCOHOLS ............................................................. 81 2.4.2 AEROBIC DEHYDROGENATION OF ALCOHOLS ............................................................... 86 2.4.3 ACCEPTORLESS DEHYDROGENATION OF ALCOHOLS AND AMINES ................................. 88 2.4.3.1 ACCEPTORLESS DEHYDROGENATION OF ALCOHOLS ....................................................... 88 2.4.3.2 ACCEPTORLESS DEHYDROGENATIVE COUPLING OF ALCOHOLS ........................................ 95 2.4.3. 2.1 SYNTHESIS OF ESTERS AND LACTONES ................................................... 95 2.43.2.2 ACCEPTORLESS DEHYDROGENATION OF ALCOHOLS COMBINED WITH DEHYDRATIVE CONDENSATIONS .............................................................................. 97 2.4.3.3 ACCEPTORLESS DEHYDROGENATIVE COUPLING OF ALCOHOLS AND AMINES ..................... 98 2.433.1 SYNTHESIS OF CARBOXAMIDES AND IMINES ............................................................. 98 2.433.2 SYNTHESIS OF HETEROCYCLES .................................................................................. 101 2.43.4 ACCEPTORLESS DEHYDROGENATION OF AMINES ........................................................ 102 2.4.4 DEHYDROGENATION OF ALKANES ......................................................................... 104 2 . 4 . 4.1 DEHYDROGENATION OF HYDROCARBONS ................................................................... 104 2.4.4.2 DEHYDROGENATION OF ALDEHYDES AND KETONES AS FUNCTIONALIZED ALKANES ......... 106 2.5 BIOMIMETIC OXIDATION IN ORGANIC SYNTHESIS L. VICENS, M. BORRELL, AND M. COSTAS 2.5 BIOMIMETIC OXIDATION IN ORGANIC SYNTHESIS .................................................. 113 2.5.1 P450-LIKE OXIDATIONS AND RELATED REACTIONS ..................................................... 114 2.5.1.1 METALLOPORPHYRINS AS CH OXIDATION CATALYSTS ................................................. 114 2.5.12 HALIDE AND PSEUDOHALIDE TRANSFER WITH METALLOPORPHYRINS ................................ 119 2 . 5.2 NON-HEME IRON-DEPENDENT OXYGENASES AS MODELS FOR OXIDATION CATALYSTS * 125 2 . 5 . 2.1 CH OXIDATIONS WITH NON-HEME IRON COMPLEXES ........................... 125 2 . 5 . 2 .2 IRON-CATALYZED SYN-DIHYDROXYLATION ........................................................ 131 2 . 5.23 IRON-CATALYZED ASYMMETRIC C/S-DIHYDROXYLATION ................................................ 134 2.5.2.4 IRON-CATALYZED EPOXIDATION ........................ - - ................................................ 135 2 . 5 . 2 .5 IRON-CATALYZED ASYMMETRIC EPOXIDATION ............................................................ 140 2.5.3 COPPER-CATALYZED BIOMIMETIC OXIDATIONS ........................................................ 143 2.53.1 SELECTIVE ALIPHATIC CH OXIDATION WITH DICOPPER COMPLEXES .......................... 144 2 . 53.2 GALACTOSE OXIDASE RELATED OXIDATIONS ............................................................. 145 2.53.2.1 ALCOHOL OXIDATION WITH COPPER COMPOUNDS AND 2,2,6,6-TETRAMETHYLPIPERIDIN-L-OXYL (TEMPO) AND RELATED RADICALS ............... 145 2.5.3.3 ORTHO-HYDROXYLATION OF PHENOLS WITH TYROSINASE MODELS ................................. 148 3 METAL-CATALYZED OXIDATION OF ALKANES TO GIVE ESTERS OR AMINES A. CABALLERO, M. M. DFAZ-REQUEJO, AND P. J. PEREZ 3 METAL-CATALYZED OXIDATION OF ALKANES TO GIVE ESTERS OR AMINES ................ 155 3.1 METAL-CATALYZED OXIDATION OF ALKANES TO ESTERS USING DIAZO COMPOUNDS * 156 3.1.1 SEMINAL STUDIES IN CARBENE TRANSFER TO CH BONDS OF ALKANES ...................... 160 3.1.2 RHODIUM-BASED CATALYSTS ................................................................................... 160 3.1.3 COINAGE-METAL-BASED CATALYSTS .......................................................................... 163 3.1.4 CATALYSTS BASED ON OTHER METALS ....................................................................... 166 3.1.5 METHANE AND GASEOUS ALKANES AS SUBSTRATES .................................................... 166 3.1.6 ASYMMETRIC CARBENE INSERTION FROM DIAZO COMPOUNDS ........................ 169 3.2 METAL-CATALYZED OXIDATION OF ALKANES TO AMINES .............................................. 169 3.2.1 ALKANE CONVERSION INTO AMINES BY NITRENE INSERTION ........................................ 170 3.2.1 .1 CYCLOALKANES AS SUBSTRATES .................................................................................. 170 3.2.1 .1.1 USING ISOLATED HYPERVALENT LODINE(LLL) SOURCES ................................................... 171 3.2.1. 1.2 USING IN SITU GENERATED HYPERVALENT LODINE(LLL) SOURCES ................................... 173 3.2.1. 1 .3 USING ORGANIC AZIDES ........................................................................................... 175 3.2.1 .2 LINEAR AND BRANCHED ALKANES AS SUBSTRATES ........................................................ 178 3.2.2 ALKANE AMINATION REACTIONS INVOLVING SUBSTITUTION OF A HYDROGEN ATOM ....... 180 3 . 2 . 2.1 ISOCYANATES AS THE NITROGEN SOURCE ................................................................... 180 3.2.2. 2 AZOLES AND DERIVATIVES AS THE NITROGEN SOURCE ................................................. 181 3 . 2.2.3 AMINES OR AMIDES AS THE NITROGEN SOURCE ........................................................ 182 3.3 SUMMARY AND OUTLOOK ........................................................................................ 185 4 ALLYLIC, BENZYLIC, AND PROPARGYLIC OXIDATION P. CHEN AND G. LIU 4 ALLYLIC, BENZYLIC, AND PROPARGYLIC OXIDATION ................................................... 191 4.1 ALLYLIC OXIDATION .................................................................................................. 191 4.1.1 ALLYLIC OXYGENATION ............................................................................................. 191 4.1.1.1 ALLYLIC OXYGENATION VIA A HYDROGEN-ATOM ABSTRACTION PROCESS ....................... 192 4.1.1.2 ALLYLIC OXYGENATION VIA A CONCERTED METALATION-DEPROTONATION PROCESS ........ 194 4.1.1.3 ALLYLIC OXYGENATION VIA OTHER PROCESSES ............................................................. 196 4.1.2 ALLYLIC AMINATION ................................................................................................. 197 4 . 1 . 2.1 ALLYLIC AMINATION VIA A HYDROGEN-ATOM ABSTRACTION PROCESS ............................ 197 4.1.2. 2 ALLYLIC AMINATION VIA A CONCERTED METALATION-DEPROTONATION PROCESS ........... 197 4.1.2 3 ALLYLIC AMINATION INVOLVING NITRENE INSERTION .................................................... 198 4.1.3 4.1.31 4.1.32 4.1.4 4.1.4.1 4.1.42 4.1.5 4.2 4.2.1 4.2.1.1 4.2.1.2 4.2.1.3 4.2.2 4.2.2.1 4.2.2.2 4.2.23 4.2.3 4.23.1 4.23.2 4.2.3.3 4.2.4 4.2.4.1 4.2.4.2 4.2.5 4.2.6 4.3 5 5.1 5.1 5.1.1 5.1.1.1 ALLYLIC ALKYLATION AND ARYLATION ......................................................................... ALLYLIC ALKYLATION AND ARYLATION VIA A HYDROGEN-ATOM ABSTRACTION PROCESS ALLYLIC ALKYLATION AND ARYLATION VIA A CONCERTED METALATION-DEPROTONATION PROCESS .............................................. . .................. ALLYLIC FLUORINATION .............................................. ............................................... ALLYLIC FLUORINATION VIA A HYDROGEN-ATOM ABSTRACTION PROCESS ........................ ALLYLIC FLUORINATION VIA A CONCERTED METALATION-DEPROTONATION PROCESS ......... ALLYLIC SILYLATION .................................................................................................. BENZYLIC OXIDATION ............................................................................................. BENZYLIC OXYGENATION .................................................................... .................... BENZYLIC OXYGENATION VIA A HYDROGEN-ATOM ABSTRACTION PROCESS ................... BENZYLIC OXYGENATION VIA A CONCERTED METALATION-DEPROTONATION PROCESS * * * BENZYLIC OXYGENATION VIA AN IMINE-ENAMINE TAUTOMERIZATION PROCESS .......... BENZYLIC AMINATION ............................................................................................ BENZYLIC AMINATION VIA A HYDROGEN-ATOM ABSTRACTION PROCESS ...................... BENZYLIC AMINATION VIA A CONCERTED METALATION-DEPROTONATION PROCESS ....... BENZYLIC AMINATION VIA NITRENE INSERTION ........................................... . ............. BENZYLIC ARYLATION AND ALKYLATION ...................................................................... BENZYLIC ARYLATION AND ALKYLATION VIA A HYDROGEN-ATOM ABSTRACTION PROCESS * BENZYLIC ARYLATION VIA A CONCERTED METALATION-DEPROTONATION PROCESS .......... BENZYLIC ALKYLATION VIA CARBENE INSERTION .......................................................... BENZYLIC FLUORINATION .......................................................................................... BENZYLIC FLUORINATION VIA A HYDROGEN-ATOM ABSTRACTION PROCESS ..................... BENZYLIC FLUORINATION INVOLVING CONCERTED METALATION-DEPROTONATION CH ACTIVATION .................................................................................................. BENZYLIC SILYLATION ............................................................................................. BENZYLIC BORYLATION .................................................* ........................................ PROPARGYLIC OXIDATION ........................................................................................ 198 198 199 202 202 203 203 203 203 204 211 213 214 214 218 220 225 225 228 229 230 231 234 235 237 239 OXIDATION OF ALKENES EPOXIDATION OF ALKENES A. BERKESSEL, H. ENGLER, AND T. M. LEUTHER EPOXIDATION OF ALKENES ................................................................................... 245 EPOXIDATION OF NONFUNCTIONALIZED ALKENES ..................................... ................. 245 ENANTIOSELECTIVE EPOXIDATION WITH TITANIUM-BASED CATALYSTS .......................... 245 5 . 1 . 1 . 1.1 USING TRONS-CYCLOHEXANEDIAMINE-DERIVED TITANIUM-SALAN COMPLEXES * * * * 245 5 . 1 . 1 . 1.2 USING C/S- AND TRANS-CYCLOHEXANEDIAMINE-DERIVED TITANIUM-SALALEN COMPLEXES ........................................................................................................... 248 5 . 1 . 1 .2 ENANTIOSELECTIVE EPOXIDATION WITH IRON-BASED CATALYSTS ................................... 251 5 . 1 . 1 . 2.1 USING IRON-PORPHYRIN COMPLEXES ....................................................................... 251 5.1.1. 2.2 USING NON-PORPHYRIN IRON COMPLEXES ................................................................ 252 5.1.13 ENANTIOSELECTIVE EPOXIDATION WITH MANGANESE-BASED CATALYSTS ....................... 255 5.1.13.1 USING MANGANESE-SALEN CATALYSTS ..................................................................... 255 5.1.13.2 USING MANGANESE-TETRAAMINE (N4) COMPLEXES ............................................... 259 5.1.1.4 ENANTIOSELECTIVE EPOXIDATION WITH RUTHENIUM-BASED CATALYSTS ....................... 264 5.1 .1.5 ENANTIOSELECTIVE EPOXIDATION WITH ORGANOCATALYSTS .......................................... 265 5.1 .1.5.1 CHIRAL KETONE CATALYZED ENANTIOSELECTIVE EPOXIDATION ..................................... 265 5.1.1.5.2 CHIRAL IMINIUM SALT CATALYZED ENANTIOSELECTIVE EPOXIDATION ............................ 266 5.1.1.6 ENANTIOSELECTIVE EPOXIDATION BY ENZYMATIC METHODS ......................................... 267 5.1.2 EPOXIDATION OF ALLYLIC AND HOMOALLYLIC ALCOHOLS ................................................ 273 5.1.2.1 ENANTIOSELECTIVE EPOXIDATION WITH TITANIUM-BASED CATALYSTS ........................... 273 5.1. 2.2 ENANTIOSELECTIVE EPOXIDATION WITH ZIRCONIUM- AND HAFNIUM-BASED CATALYSTS * 274 5.1.23 ENANTIOSELECTIVE EPOXIDATION WITH VANADIUM-BASED CATALYSTS ......................... 277 5 . 1 .2.4 ENANTIOSELECTIVE EPOXIDATION WITH TUNGSTEN-BASED CATALYSTS ........................... 278 5 . 1.3 EPOXIDATION OF ACCEPTOR-SUBSTITUTED ALKENES .................................................... 280 5.13.1 ENANTIOSELECTIVE EPOXIDATION WITH MANGANESE-BASED CATALYSTS ...................... 280 5.13.2 ENANTIOSELECTIVE EPOXIDATION WITH IRON-BASED CATALYSTS ................................... 283 5.1.3.3 ENANTIOSELECTIVE EPOXIDATION WITH OTHER METAL CATALYSTS .................................. 288 5.13.4 ENANTIOSELECTIVE EPOXIDATION WITH POLYAMINO ACID CATALYSTS .......................... 291 5.13.5 ENANTIOSELECTIVE EPOXIDATION WITH ORGANOCATALYSTS ......................................... 292 5.13.5.1 USING A,A-DIARYK-PROLINOLS AND RELATED CATALYSTS ........................................... 292 5.13.5.2 USING CINCHONA ALKALOID CATALYSTS ..................................................................... 296 5.13.53 PHASE-TRANSFER CATALYSIS ....................................................................................... 300 5.2 DIOXYGENATION OF ALKENES C. MARTINEZ AND K. MUNIZ 5.2 DIOXYGENATION OF ALKENES ............................................................................... 309 5.2.1 THE SHARPLESS DIHYDROXYLATION ............................................................................ 309 5 . 2 . 1 .1 SECOND CYCLE CATALYSIS ......................................................................................... 322 DIHYDROXYLATION OF ALKENES CATALYZED BY RUTHENIUM OXIDANTS ........................ 325 5.2.2 5 . 2.3 METAL-FREE DIHYDROXYLATION OF ALKENES ............................................................. 328 5.2.3.1 METAL-FREE ENANTIOSELECTIVE DIOXYGENATION MEDIATED BY HYPERVALENT LODINE(LLL) ........................................................................................................... 329 5 . 2.4 CONCLUSIONS ..................................................................................... 339 5.3 AMINOHYDROXYLATION AND AMINOOXYGENATION OF ALKENES S. R. CHEMLER AND T. WDOWIK 5.3 AMINOHYDROXYLATION AND AMINOOXYGENATION OF ALKENES ........................... 343 5 . 3.1 INTERMOLECULAR AMINOOXYGENATION AND AMINOHYDROXYLATION .......................... 343 5.3.1.1 OSMIUM-CATALYZED INTERMOLECULAR AMINOHYDROXYLATION ................................. 344 5 . 3 . 1 .1.1 OSMIUM-CATALYZED AMINOHYDROXYLATION OF ARYLALKENES ................................... 345 5 . 3 . 1 .1.2 OSMIUM-CATALYZED AMINOHYDROXYLATION OF A,SS-UNSATURATED ESTERS ................ 350 5 . 3 . 1 .1.3 OSMIUM-CATALYZED AMINOHYDROXYLATION OF UNACTIVATED ALKENES .................... 351 5.3.1.2 COPPER-CATALYZED INTERMOLECULAR AMINOOXYGENATION ...................................... 352 5.3.1.3 IRON-CATALYZED INTERMOLECULAR AMINOOXYGENATION ............................................ 354 5.3.1.4 RHODIUM-CATALYZED INTERMOLECULAR AMINOOXYGENATION ................................... 359 5.3.1.5 PALLADIUM-CATALYZED INTERMOLECULAR AMINOACETOXYLATION ................................ 361 5 . 3 . 1 .6 MANGANESE-CATALYZED INTERMOLECULAR HYDROXYAZIDATION .................................. 362 5.3.1.7 (ACETYLAMINO)OXYGENATION OF GLUCALS ................................................................ 364 5 . 3.2 INTRAMOLECULAR AMINOHYDROXYLATION AND AMINOOXYGENATION TO FORM NITROGEN HETEROCYCLES ....................................................................................... 365 5 . 3 . 2.1 OSMIUM-CATALYZED INTRAMOLECULAR AMINOHYDROXYLATION .................................. 366 5.3.2 .2 COPPER-CATALYZED INTRAMOLECULAR AMINOOXYGENATION ....................................... 368 S.3.2.3 IRON-CATALYZED INTRAMOLECULAR AMINOOXYGENATION ............................................ 371 S.3.2.4 RHODIUM-CATALYZED INTRAMOLECULAR AMINOOXYGENATION .................................... 373 5 . 3 . 2 .S PALLADIUM-CATALYZED INTRAMOLECULAR AMINOOXYGENATION .................................. 374 5.3.2.6 HYPERVALENT-LODINE-MEDIATED INTRAMOLECULAR AMINOOXYGENATION ..................... 376 5.3.3 INTRAMOLECULAR AMINOOXYGENATION AND OXYAZIDATION REACTIONS TO FORM OXYGEN HETEROCYCLES ............................................................................. 381 5.33.1 PALLADIUM-CATALYZED INTRAMOLECULAR AMINOOXYGENATION ................................ 381 5 . 33.2 COPPER-PROMOTED OR -CATALYZED INTRAMOLECULAR AMINOOXYGENATION AND OXYAZIDATION ...................................................................................................... 382 5.3.33 METAL-FREE INTRAMOLECULAR AMINOOXYGENATION OF UNSATURATED HYDROXAMIC ACIDS ........................................................* ................................... 385 5.4 HALOGENATION AND HALOCYDIZATION OF ALKENES A. ANDRIES-ULMER AND T. GULDEN 5.4 HALOGENATION AND HALOCYDIZATION OF ALKENES ............................................... 389 5.4.1 CHEMOSELECTIVE HALOFUNCTIONALLZATLON .............................................................. 390 5.4.1 .1 BROMOCARBOCYCLIZATION CATALYZED BY HYPERVALENT LODANES ........................... . * 390 5.4.1 .2 REARRANGEMENT CATALYZED BY HYPERVALENT LODANES ........................................... 392 5.4.1 .3 ORGANOCATALYTIC DIHALOGENATION ......................................................................... 394 5.4.2 DIASTEREOSELECTIVE SYN HALOFUNCTIONALLZATLON .................................................... 398 5.4.2.1 SYN DICHLORINATION CATALYZED BY SELENIUM ......................................................... 398 5.4.3 ASYMMETRIC HALOFUNCTIONALLZATLON ..................................................................... 400 5.4.3.1 CHIRAL ION-PAIRING CATALYSIS ................................................................................. 402 5.4.3.U HALOETHERIFICATION CATALYZED BY 1,1 -BI-2-NAPHTHOL-DERIVED PHOSPHORIC ACID DERIVATIVES .................................................................................................. 402 5.4.3.1.2 HALOLACTONIZATION CATALYZED BY BIFUNCTIONAL 1,1 -BINAPHTHYL-DERIVED AMIDINES 404 5.4.3.1.3 INTERMOLECULAR BROMOAMIDATION CATALYZED BY 1,1 -BI-2-NAPHTHOL-DERIVED PHOSPHORIC ACID DERIVATIVES ............................................................................... 405 S.4.3.1.4 INTRAMOLECULAR HALOCYDIZATION BY CHIRAL ANION PHASE-TRANSFER CATALYSIS .......... 405 5.4.3.15 BROMOLACTONIZATION CATALYZED BY C3-SYMMETRIC TRISIMIDAZOLINES ................... 407 5.4.3.16 HALOCYDIZATION CATALYZED BY CHIRAL AMINO UREAS ............................................. 409 5.4.3. 2 CHIRAL LEWIS BASE CATALYSIS .................................................................................. 412 5.4.3.2.1 BROMOAMINOCYCLIZATION CATALYZED BY SELENIUM LEWIS BASES ............................ 412 5.4.3.2.2 BROMOETHERIFICATION OF PROCHIRAL DIOLS CATALYZED BY SULFUR LEWIS BASES ............ 413 5.4.3.23 BROMOOXYCYCLIZATION CATALYZED BY PHOSPHORUS LEWIS BASES ............................. 414 5.4.33 CHIRAL HYDROGEN-BONDING CATALYSIS .................................................................... 415 5.433.1 BROMOLACTAMIZATION CATALYZED BY QUINIDINE-DERIVED CARBAMATES ................. 415 5.433.2 DESYMMETRIZATION VIA BROMOETHERIFICATION CATALYZED BY O-ALKYL THIOCARBAMATES .................................................................................................. 416 5.4.3.3.3 BROMOLACTONIZATION CATALYZED BY PROLINE-DERIVED 5-ALKYL AND O-ALKYL THIOCARBAMATES ...................................................................................... 417 5.433.4 BROMINE-INDUCED SEMIPINACOL REARRANGEMENT CATALYZED BY DIMERIC CINCHONA ALKALOIDS ............................................................................................. 418 5.4 3 3 .5 DIHALOGENATION CATALYZED BY DIMERIC ALKALOIDS ................................................ 419 5.43.4 CHIRAL LEWIS ACID CATALYSIS ............................................................................. . * 420 5.43.4.1 LODOCARBOCYCLIZATION OF MALONATES CATALYZED BY TITANIUM(IV) LEWIS ACIDS * 420 5.43.4.2 DIBROMINATION OF CINNAMYL ALCOHOLS CATALYZED BY TITANIUM(IV) LEWIS ACIDS * * 422 5.43.43 LODOETHERIFICATION CATALYZED BY COBALT(LL) LEWIS ACIDS ..................................... 423 5.43.4.4 INTERMOLECULAR CHLOROAMINATION CATALYZED BY SCANDIUM(LLL) LEWIS ACIDS ....... 424 5.5 THE WACKER PROCESS N. J. RACE, H. H. PATEL, AND M. S. SIGMAN 5.5 THE WACKER PROCESS ....................................... . ......................... . .................... 429 5.5.1 KETONE-SELECTIVE WACKER OXIDATIONS ................................................................. 430 5.5.1.1 DIRECT MOLECULAR OXYGEN COUPLED CONDITIONS .................................................. 430 5.5.1 .2 PEROXIDE-BASED WACKER OXIDATIONS ................................................................... 432 5.5.13 WACKER OXIDATION OF PROTECTED ALLYLIC AMINES ....... - ........................................ 435 5.5.1.4 WACKER OXIDATION OF HOMOALLYLIC ALCOHOLS ........................................................ 436 5 . 5.2 ALDEHYDE-SELECTIVE WACKER OXIDATIONS ........................................ 437 5 . 5 . 2.1 WACKER OXIDATION OF TERMINAL ALKENES: UNBIASED SUBSTRATES .......................... 437 5 . 5 . 2 .2 WACKER OXIDATION OF PHTHALIMIDE-PROTECTED ALLYLIC AMINES .............................. 439 5 . 5.23 WACKER OXIDATION OF ALLYLIC ESTERS ...................................................................... 440 S.5.2.4 WACKER OXIDATION OF STYRENE DERIVATIVES ........................................................... 440 5.5.25 WACKER OXIDATION OF ALLYLIC FLUORIDES ..................................... 441 5 . 5.25 WACKER OXIDATION OF STERICALLY HINDERED TERMINAL ALKENES ............................. 443 5.5.3 WACKER OXIDATION OF INTERNAL ALKENES ................................................ 445 5 . 53.1 INDUCTIVE EFFECTS IN THE WACKER OXIDATION OF INTERNAL ALKENES ......................... 447 6 SULFINYL- AND SULFONYL-CONTAINING DIRECTING GROUPS IN CH OXIDATION OF ARENES R. GOEMEZ-ARRAYAS AND N. RODRIGUEZ 6 SULFINYL- AND SULFONYL-CONTAINING DIRECTING GROUPS IN CH OXIDATION OF ARENES . ............. . ........................................................................................... 449 6.1 SULFINYL-BASED DIRECTING GROUPS ....................................................................... 451 6 . 1.1 ARYL SULFOXIDE BASED DIRECTING GROUPS ............................................................. 451 6 . 1 . 1.1 OXIDATIVE CH BOND ARYLATION OF ARENES ............. . ............................................ 451 6.1.1.2 REDOX-NEUTRAL C-H BOND ARYLATION OF ARENES ................................................... 453 6 . 1.13 DIRECTED CH BOND ALKENYLATION OF ARENES ..................................................... 453 6.1.2 REMOVABLE 2-PYRIDYLSULFINYL GROUP ASSISTED C -H BOND ACTIVATION * . ............... 456 6.1.2.1 DIRECT C-H BOND ALKENYLATION OF ARENES ........................................................... 456 6.1.2.2 DIRECT C -H BOND ARYLATION OF ARENES ................................................................ 457 6.1.2.2.1 SUZUKI-MIYAURA-TYPE COUPLING .............. 457 6.1.2.2.2 DEHYDROGENATIVE ARYLATION ............................................. 458 6.1.23 DIRECT C-H BOND ALKYLATION OF ARENES ............................................................. 458 6.1.24 C -H ACETOXYLATION ........................................................................................... 459 6.1.3 SULFOXIDES AS CHIRAL DIRECTING GROUPS ............................................................... 459 6 . 1.31 DIRECT CH BOND ALKENYLATION OF ARENES ............................................................ 460 6.1.3 2 OTHER SULFOXIDE-DIRECTED ASYMMETRIC MILD CH FUNCTIONALIZATION PROCESSES * 461 6.2 SULFONAMIDE-BASED DIRECTING GROUPS ................................................................. 462 6 . 2.1 N-SULFONYLANILINE AND N-SULFONYL(ARYLALKYL)AMINE DERIVATIVES .......................... 462 6 . 2.2 ARENE- AND ARYLALKANESULFONAMIDE DERIVATIVES ................................................ 469 6.3 SULFONE-BASED DIRECTING GROUPS ........................................................................ 473 6.4 SUMMARY AND OUTLOOK ........................................................................................ 476 7 GOLD-CATALYZED OXIDATION OF ALKYNES P. CALLEJA, R. DOREL, AND A. M. ECHAVARREN 7 GOLD-CATALYZED OXIDATION OF ALKYNES ............................................................ 479 7.1 MECHANISM ......................................................................................................... 479 7.2 OXIDATIVE REACTIONS OF ALKYNES .......................................................................... 480 7.2.1 INTRAMOLECULAR OXIDATION OF ALKYNES ................................................................. 480 7 . 2.2 INTERMOLECULAR OXIDATION OF ALKYNES .................................................................. 489 7 . 2 . 2.1 INTRAMOLECULAR TRAPPING OF A-OXO GOLD CARBENES ............................................. 490 7.2.2.2 INTERMOLECULAR TRAPPING OF A-OXO GOLD CARBENES .............................................. 497 7.3 OXIDATIVE REACTIONS OF ENYNES ............................................................................ 508 7.4 APPLICATIONS IN TOTAL SYNTHESIS ............................................................................ 520 8 OXIDATION OF ALCOHOLS 8.1 RECENT DEVELOPMENTS IN CATALYTIC ALCOHOL OXIDATION USING IMITROXYL RADICALS L. M. DORNAN, N. L. HUGHES, AND M. J. MULDOON 8.1 RECENT DEVELOPMENTS IN CATALYTIC ALCOHOL OXIDATION USING IMITROXYL RADICALS .............................................................................................. 529 8 . 1.1 MECHANISTIC UNDERSTANDING ............................................................................... 530 8.1.2 OXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES ............................................. 533 8.1.21 HYPOCHLORITE AND HYPERVALENT IODINE BASED OXIDATIONS ................................... 533 8.1.2 2 IMITROXYL RADICAL/NOX BASED SYSTEMS .................................................................. 537 8 . 1 . 2 . 2.1 ANAEROBIC OXIDATIONS ............................................................. 537 8 . 1 . 2 . 2.2 AEROBIC IMITROXYL RADICAL/NOX SYSTEMS .............................................................. 539 8 . 1.2 3 NITROXYL RADICAL/COPPER SALT SYSTEMS .................................................................. 541 8 . 1 . 2 . 3.1 COPPER/TEMPO OXIDATION OF PRIMARY ALCOHOLS .................................................... 541 8 . 1 . 2 . 3.2 COPPER/NITROXYL RADICAL OXIDATION OF SECONDARY ALCOHOLS ................................. 542 8.1.2.3.3 COPPER/NITROXYL RADICAL OXIDATION OF AMINO ALCOHOLS INTO AMINO CARBONYL COMPOUNDS .................................................................... 544 8.1.2.3.4 COPPER/NITROXYL RADICAL SYSTEMS FOR THE SELECTIVE OXIDATION OF VIOLS ............ 546 8.1.3 SYNTHESIS OF NITRILES VIA ALCOHOL OXIDATION .......................................................... 549 8.1.4 OXIDATION OF ALCOHOLS AND AMINES TO IMINES ........................................................ 550 8.1.5 OXIDATION OF ALCOHOLS AND AMINES TO AMIDES ...................................................... 551 8 . 1.6 OXIDATION OF ALCOHOLS TO CARBOXYLIC ACIDS ........................................................... 553 8 . 1 . 6.1 1-ME-AZADO OXOAMMONIUM SALTS AND SODIUM CHLORITE ................................... 553 8.1.6.2 OXIDATION OF ALCOHOLS TO CARBOXYLIC ACIDS USING HYPERVALENT IODINE AS THE TERMINAL OXIDANT ......................................................................... 556 8.1.6.3 OXIDATIVE CLEAVAGE OF TERMINAL VIOLS TO DEHOMOLOGATED CARBOXYLIC ACIDS * * * 557 8 . 1 .6.4 OXIDATION OF 1.2-VIOLS TO A-HYDROXY ACIDS AND FURTHER OXIDATION TO A-OXO ACIDS * . .................................................................................................. 559 8.1.7 SAFETY AND SCALABILITY .......................................................................................... 563 8.2 ENANTIOSELECTIVE OXIDATION OF ALCOHOLS B. M. STOLTZ, A. C. WRIGHT, V. C. EBNER, AND N. PARK 8.2 ENANTIOSELECTIVE OXIDATION OF ALCOHOLS .......................................................... 569 8.2.1 KINETIC RESOLUTION VIA TRANSFER HYDROGENATION .................................................... 570 8 . 2.2 KINETIC RESOLUTION/DESYMMETRIZATION USING MOLECULAR OXYGEN AS TERMINAL OXIDANT ................................................................................................. 571 8 . 2 . 2.1 PALLADIUM-CATALYZED OXIDATIVE KINETIC RESOLUTION OF SECONDARY ALCOHOLS * 571 8.2.2.2 RUTHENIUM-CATALYZED OXIDATIVE KINETIC RESOLUTION OF SECONDARY ALCOHOLS * - * 574 S.2.2.3 IRIDIUM-CATALYZED OXIDATIVE KINETIC RESOLUTION AND DESYMMETRIZATION OF ALCOHOLS ............... . * ................................................................................... 575 S.2.2.4 IRON-CATALYZED OXIDATIVE KINETIC RESOLUTION OF SECONDARY ALCOHOLS ............ * * 576 8.2.2.5 OXIDATIVE KINETIC RESOLUTION OF HYDROXY ESTERS AND KETONES ........................ 577 8.2.3 KINETIC RESOLUTION OF SECONDARY ALCOHOLS USING NITROXYL RADICAL BASED SYSTEMS .................................................... - - ................................................... 578 8 . 2.4 KINETIC RESOLUTION OF SECONDARY ALCOHOLS USING MANGANESE-SALEN COMPLEXES 580 8.2.5 BIOCATALYTIC KINETIC RESOLUTION OF SECONDARY ALCOHOLS ........................................ 582 8 . 2 . 5.1 BACTERIAL KINETIC RESOLUTIONS ............................................................................... 582 9 CATALYTIC AEROBIC OXIDATION OF PHENOLS J.-P. LUMB AND K. V. N. ESGUERRA 9 CATALYTIC AEROBIC OXIDATION OF PHENOLS ........................................................... 587 9.1 OXIDATIVE DIMERIZATION OF PHENOLS ....................................................................... 589 9.1.1 OXIDATIVE CC DIMERIZATION OF PHENOLS TO BIPHENOLS ........................................ 590 9.1.1.1 OXIDATIVE DIMERIZATION USING HOMOGENEOUS CATALYSTS .............................................. 590 9.1 .1.2 OXIDATIVE DIMERIZATION USING HETEROGENEOUS CATALYSTS ..................................... 594 9.1.13 REGIOSELECTIVE CROSS COUPLING .............................................................................. 594 9.1.1.4 STEREOSELECTIVE CROSS COUPLING ............................................................................. 595 9.1.2 OXIDATIVE CC DIMERIZATION AND OXIDATION OF PHENOLS TO PUMMERER S KETONE 596 9.1.3 OXIDATIVE CC DIMERIZATION AND RING EXPANSION ............................................... 598 9.2 OXIDATIVE POLYMERIZATION OF PHENOLS ................................................................... 602 9.3 AEROBIC INTRAMOLECULAR ARENE-PHENOL COUPLING ........................................ 606 9.4 OXYGENATION OF PHENOLS TO QUINONES .................................................................. 609 9.4.1 OXIDATION OF PHENOLS TO BENZO-1,4-QUINONES ...................................................... 610 9.4.2 OXIDATION OF PHENOLS TO BENZO-1,2-QUINONES ...................................................... 618 9.5 AEROBIC NITRATION AND AMINATION OF PHENOLS ....................................................... 623 9.6 CATALYTIC AEROBIC HALOGENATION OF PHENOLS ......................................................... 626 10 A-OXIDATION OF CARBONYL COMPOUNDS M. UYANIK AND K. ISHIHARA IO A-OXIDATION OF CARBONYL COMPOUNDS ............................................................... 635 10.1 METAL CATALYSIS ...................................................................................................... 635 10.1.1 A-HYDROXYLATION .................................................................................................... 635 10 . 1.2 OXIDATIVE A-CO COUPLING ................................................................................... 639 10.13 OXIDATIVE A-CN COUPLING ................................................................................... 641 10.2 ENANTIOSELECTIVE ORGANOCATALYSIS ........................................................................ 643 10 . 2.1 PHASE-TRANSFER CATALYSIS ........................................................................................ 643 10 . 2.2 ORGANOBASE CATALYSIS ........................................................................................... 646 10.2.3 CHIRAL KETONE CATALYZED EPOXIDATION OF ENOL ESTERS ........................................... 647 10.3 IODINE-BASED CATALYSIS .......................................................................................... 649 10.3.1 ORGANOIODINE(LLL) CATALYSIS ................................................................................... 650 10.3.1 .1 A-ACYLOXYLATION ..................................................................................................... 650 10.3.12 A-TOSYLOXYLATION ..................................................................................................... 651 10.3.2 INORGANIC IODINE CATALYSIS ............................................................................. 554 10 . 3 . 2.1 A-ACYLOXYLATION ................................................................................................. 554 10 . 3 . 2.2 OXIDATIVE COUPLING OF CARBONYL COMPOUNDS WITH PHENOLS ............................. 658 10 . 3 . 2.3 CC-HYDROXYLATION ............................................................................ 55G 10 . 3 . 2.4 OXIDATIVE A-CN COUPLING ................................................................................ 661 10 . 3 . 2.5 ENANTIOSELECTIVE A-OXIDATIVE COUPLING .............................................................. 666 11 OXIDATION OF AMINES AND N-HETARENES N. JIAO AND Z. LI 11 OXIDATION OF AMINES AND IM-HETARENES ............................................................ 671 II- I CATALYTIC OXIDATION OF AMINES ............................................................................ 671 H- I-I DIRECT OXIDATION OF SECONDARY AMINES TO IMINES .............................................. 671 11-1-2 OXIDATION OF PRIMARY AMINES TO IMINES ............................................................. 674 11 . 1.3 OXIDATION OF AMINES TO NITRILES ................................................... 676 11 . 1.4 OXIDATION OF AMINES TO OXIMES .......................................................................... 678 11 . 1.5 OXIDATION OF AMINES TO NITROSO COMPOUNDS .................................................... 680 H I-6 OXIDATION OF AMINES TO NITRO COMPOUNDS ......................................................... 680 11 . 1.7 OXIDATION OF AMINES TO /V-OXIDES ...................................................................... 682 11 . 1 . 7.1 OXIDATION OF TERTIARY AMINES TO N-OXIDES ........................................................ 682 11 . 1 . 7.2 OXIDATION OF SECONDARY AMINES TO NITRONES ..................................................... 685 11 . 1.73 OTHER OXIDATIONS ON THE NITROGEN ATOM ........................................................... 687 11 . 1.8 OXIDATION OF AMINES TO AMIDES ......................................................................... 689 111 . 8.1 OXIDATION OF METHYLAMINES TO FORMAMIDES ..................................................... 689 111 . 8.2 OXIDATION OF BENZYLIC AMINES TO BENZAMIDES ................................................... 689 11.1.83 OXIDATION OF CYCLIC AMINES TO LACTAMS .............................................................. 690 11.1.8 4 OXIDATION OF COMMON ALIPHATIC AMINES TO AMIDES .......................................... 691 11 . 1.9 OXIDATION OF AMINES TO DIAZENES AND DERIVATIVES .......... - ................................ 692 111 . 9.1 OXIDATION OF AMINES TO DIAZENE OXIDES OR DIOXIDES BY HYDROGEN PEROXIDE * * * 692 11 . 1.9 2 AEROBIC OXIDATION OF AMINES TO DIAZENES ......................................................... 693 11 . 1.93 OXIDATION OF AMINES TO DIAZENES BY OTHER OXIDANTS ........................................ 694 11 . 1.10 PHOTOCATALYZED OXIDATION OF AMINES TO IMINES AND NITRILES ........................... 695 11 . 1.11 BIOCHEMICAL AND BIOMIMETIC CATALYSIS IN AMINE OXIDATION ............................. 697 11 . 1 . 11.1 BIOCHEMICAL OXIDATION OF AMINES BY ENZYMES ............ ..................................... 697 11 . 1.112 BIOMIMETIC OXIDATION OF AMINES BY FLAVIN DERIVATIVES .................................... 698 11 . 1.113 BIOMIMETIC OXIDATION OF AMINES BY QUINONE DERIVATIVES ............................. . 701 11.2 CATALYTIC OXIDATION OF HETARENES ....................................................................... 702 11 . 2.1 OXIDATION OF SIX-MEMBERED HETARENES TO GIVE N-OXIDES ................................. 703 N.2.2 OXIDATION OF SIX-MEMBERED HETARENES TO GIVE PYRIDINONES ............................ 705 11.2.3 OXIDATION OF AZOLES ............................ 706 N.2.4 OXIDATION OF PYRROLES ....................................................... 708 11.2.5 OXIDATION OF INDOLES ........................................................................................... 710 11 . 2.6 OXIDATION OF PURINES ........................................................................................... 712 11 . 2.61 OXIDATION ON THE IMIDAZOLE RING OF GUANINES .................................................... 712 11 . 2.6 2 OXIDATION ON THE PYRIMIDINE RING OF ADENINES ................................................... 715 12 AEROBIC OXIDATIVE INTERMOLECULAR CROSS-COUPLING AND HECK REACTIONS F. BEILINA AND !_. A. PEREGO 12 AEROBIC OXIDATIVE INTERMOLECULAR CROSS-COUPLING AND HECK REACTIONS * * * 721 12.1 GENERAL MECHANISTIC CONSIDERATIONS OF AEROBIC OXIDATIVE COUPLINGS .............. 722 12 . 1.1 CH ACTIVATION OF ARENES AND HETARENES BY PALLADIUM(LL) COMPLEXES ............ 723 12.1.2 REGENERATION OF THE PALLADIUM CATALYST BY OXIDATION WITH MOLECULAR OXYGEN 724 12.2 AEROBIC OXIDATIVE HECK ALKENYLATION OF ARENES AND HETARENES ...................... 725 12 . 2.1 AEROBIC OXIDATIVE HECK COUPLING IN THE PRESENCE OF A CO-OXIDANT ................. 725 12 . 2 . 1.1 HETEROPOLYOXOMETALATES OF MOLYBDENUM AND VANADIUM AS CO-OXIDANT ......... 725 12 . 2.1 2 MANGANESE(LLL) SALTS AS CO-OXIDANT . .................................................................... 727 12.2.13 AMMONIUM PERSULFATE AS CO-OXIDANT ................................................................ 728 12 . 2.2 AEROBIC OXIDATIVE HECK COUPLING USING TRANSITION-METAL LIGANDS ................... 729 12 . 2.21 BENZOIC ACID AS A LIGAND ..................................................................................... 729 12 . 2.2 2 MONOPROTECTED AMINO ACIDS AS LIGANDS ........................................................... 730 12.2.2 3 PYRIDINES AND OTHER NITROGEN LIGANDS ................................................................ 732 12 . 2.2 4 THIOETHERS AS LIGANDS .......................................................................................... 735 12.2.3 DIRECTING GROUPS FOR THE AEROBIC OXIDATIVE HECK ALKENYLATION OF ARENES AND HETARENES ........................................................................................ 736 12 . 2.31 AEROBIC HECK ALKENYLATION OF ARENES .................................................................. 736 12.2.3 2 AEROBIC HECK ALKENYLATION OF HETARENES ........................................................... 739 12.3 AEROBIC OXIDATIVE CROSS COUPLING OF TWO ARENES ............................................. 740 12.3.1 AEROBIC ARYL-ARYL OXIDATIVE CROSS COUPLING .................................................. . 741 12.3.11 OXIDATIVE COUPLING OF /V-ARYLAMIDES WITH SIMPLE ARENES ................................. 741 12.3.12 OXIDATIVE COUPLING OF POLYFLUORINATED ARENES WITH SIMPLE ARENES ................. 742 12.3.2 AEROBIC HETARYL-ARYL OXIDATIVE CROSS COUPLING ................................................ 743 12.3.2.1 OXIDATIVE COUPLING OF HETARENES WITH SIMPLE ARENES ...................................... 743 12 . 3.2 2 OXIDATIVE COUPLING OF HETARENES WITH POLYFLUOROARENES ................................... 747 12 . 3.3 AEROBIC HETARYL-HETARYL OXIDATIVE CROSS COUPLING ............................................ 749 12.4 AEROBIC OXIDATIVE ALKYNYLATION OF ARENES AND HETARENES .................................. 754 12.4.1 COPPER-PROMOTED AEROBIC OXIDATIVE ALKYNYLATION OF ARENES AND HETARENES ** 754 12.4.1.1 ALKYNYLATION OF PERFLUOROARENES ........................................................................ 754 12.4.1.2 ALKYNYLATION OF HETARENES ....................................... 755 12.4.1.3 COPPER-PROMOTED ALKYNYLATION OF ARENES AND HETARENES USING DIRECTING GROUPS ................................................................................................................ 757 12 . 4.2 PALLADIUM-CATALYZED AEROBIC OXIDATIVE ALKYNYLATION OF HETARENES ................... 759 12 . 4 . 2.1 ALKYNYLATION OF AZOLES ........................................................................................ 760 KEYWORD INDEX ................................................................................................. 767 AUTHOR INDEX .................................................................................................... 797 ABBREVIATIONS 833
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spelling	Catalytic oxidation in organic synthesis volume editor K. Muñiz ; authors A. Andries-Ulmer [und weitere] Stuttgart Thieme 2018 XXXIX, 838 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier Science of synthesis 2017, 4 Science of synthesis reference library Organische Synthese (DE-588)4075695-6 gnd rswk-swf Katalytische Oxidation (DE-588)4163425-1 gnd rswk-swf Organic Chemistry Organic Synthesis Organic Reactions Organic Transformations Review Referenzwerk Organische Chemie Catalysis Green Chemistry Oxidation Organocatalysis Photocatalysis Epoxidation Dihydroxylation Wacker Process Biomimetic Oxidation Asymmetric Catalysis Chemie (DE-588)4143413-4 Aufsatzsammlung gnd-content Katalytische Oxidation (DE-588)4163425-1 s Organische Synthese (DE-588)4075695-6 s DE-604 Muniz, Kilian edt Georg Thieme Verlag KG (DE-588)1064287301 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-13-201261-5 Erscheint auch als Online-Ausgabe, EBUP 978-3-13-201271-4 B:DE-101 application/pdf http://d-nb.info/1133580580/04 Inhaltsverzeichnis DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030097910&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis
spellingShingle	Catalytic oxidation in organic synthesis Organische Synthese (DE-588)4075695-6 gnd Katalytische Oxidation (DE-588)4163425-1 gnd
subject_GND	(DE-588)4075695-6 (DE-588)4163425-1 (DE-588)4143413-4
title	Catalytic oxidation in organic synthesis
title_auth	Catalytic oxidation in organic synthesis
title_exact_search	Catalytic oxidation in organic synthesis
title_full	Catalytic oxidation in organic synthesis volume editor K. Muñiz ; authors A. Andries-Ulmer [und weitere]
title_fullStr	Catalytic oxidation in organic synthesis volume editor K. Muñiz ; authors A. Andries-Ulmer [und weitere]
title_full_unstemmed	Catalytic oxidation in organic synthesis volume editor K. Muñiz ; authors A. Andries-Ulmer [und weitere]
title_short	Catalytic oxidation in organic synthesis
title_sort	catalytic oxidation in organic synthesis
topic	Organische Synthese (DE-588)4075695-6 gnd Katalytische Oxidation (DE-588)4163425-1 gnd
topic_facet	Organische Synthese Katalytische Oxidation Aufsatzsammlung
url	http://d-nb.info/1133580580/04 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030097910&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
work_keys_str_mv	AT munizkilian catalyticoxidationinorganicsynthesis AT georgthiemeverlagkg catalyticoxidationinorganicsynthesis

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