Iron and palladium catalyzed C-H functionalization:
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| Format: | Abschlussarbeit Buch |
| Sprache: | English |
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2011
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| Online-Zugang: | Volltext https://nbn-resolving.org/urn:nbn:de:bvb:19-131598 Inhaltsverzeichnis |
| Beschreibung: | 254 S. graph. Darst. |
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| adam_text | IMAGE 1
DISSERTATION ZUR ERLANGUNG DES DOKTORGRADES
DER FAKULTAET FUER CHEMIE UND PHARMAZIE
DER LUDWIG-MAXIMILIANS-UNIVERSITAET MUENCHEN
IRON AND PALLADIUM CATALYZED C-H FUNCTIONALIZATION
WEIHAN
HUBEI, CHINA
2011
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1014188628
DIGITALISIERT DURCH
IMAGE 2
TABLE OF CONTENTS
CHAPTER 0 SUMMARY
0.1 GENERAL
0.2 FE CATALYZED C-H BOND ACTIVATION *
0.2.1 IRON CATALYZED OXIDATIVE CYANATION OF TERTIARY AMINES 1 0.2.2
IRON-CATALYZED DEHYDROGENATIVE PHOSPHONATION OFN,N- DIALKYLANILINES 4
0.3 PALLADIUM-CATALYZED DIRECT ARYLATIONS OF AZOLES WITH
ARYL SILICON AND TIN REAGENTS 5
0.4 PALLADIUM-CATALYZED DEHYDROGENATIVE CROSS COUPLINGS
OF AZOLES 7
0.5 PALLADIUM-CATALYZED DIRECT TRIFLUOROMETHYLATION OF
AZOLES VIA SP 2 C-H ACTIVATION 8
CHAPTER 1 INTRODUCTION
1.1 GENERAL OVERVIEW 10
1.2 FE-CATALYZED ORGANIC REACTIONS U
1.2.1 OVERVIEW H
1.2.2 FUNCTIONALIZATION OF SP 3 C-H BONDS ADJACENT TO NITROGEN 11
1.3 PD-CATALYZED DIRECT ARYLATION OF SP 2 C-H BONDS 22
1.3.1 OVERVIEW 22
1.3.2 PD-CATALYZED DIRECT ARYLATION OF SP 2 C-H WITH ORGANOMETALLIC
IMAGE 3
REAGENTS 26
1.3.3 PD-CATALYZED DIRECT C-H/C-H CROSS-COUPLING OF ARENES 33
1.4 TRANSITION-METAL-CATALYZED ARENE TRIFLUOROMETHYLATION 45
1.5 OBJECTIVES 53
1.6 REFERENCES 55
CHAPTER 2 IRON CATALYZED OXIDATIVE CYANATION OF
TERTIARY AMINES
2.1 INTRODUCTION 62
2.2 RESULTS AND DISCUSSION 65
2.2.1 OPTIMIZING THE CATALYTIC SYSTEM 65
2.2.2 SCOPE AND LIMITATIONS 67
2.2.3 OXYGEN AS OXIDANT 72
2.3 CONCLUSION 76
2.4 REFERENCES 77
2.5 E X P E R I M E N T AL SECTION 79
2.5.1 GENERAL 79
2.5.2 MATERIALS 7 9
2.5.3 IRON-CATALYZED CYANATION OF TERTIARY AMINES WITH /ERT-BUTYL
HYDROPEROXIDE AS OXIDANT 80
2.5.4 IRON-CATALYZED CYANATION OF TERTIARY AMINES WITH OXYGEN
AS OXIDANT 93
2.5.5 X-RAY CRYSTAL STRUCTURE ANALYSIS OF L-PHENYLPYRROLIDINE-2,5-
DICARBONITRILE 98
IMAGE 4
CHAPTER 3 IRON-CATALYZED DEHYDROGENATIVE
PHOSPHONATION OF N, VV-DIALKYLANILINES
3.1 INTRODUCTION 3.2 RESULTS AND DISCUSSION
3.2.1 A-PHOSPHONATION 3.2.2 A,A -BISPHOSPHONATIONS
3.2.3 MECHANISM
3.3 CONCLUSIONS
3.4 REFERENCES
3.5 EXPERIMENTAL SECTION
3.5.1 GENERAL 3.5.2 MATERIALS
3.5.3 TYPICAL PROCEDURE FOR THE IRON CATALYZED PHOSPHONATION OF
TERTIARY AMINES
3.5.4 PHOSPHONATED TERTIARY AMINES
3.5.5 REACTIONS OF THE N,O-ACETAL 27A WITH 2A
3.5.6 IN SITU EXPERIMENT FOR SLOW FORMATION OF CH 3 OD
3.5.7 X-RAY CRYSTAL STRUCTURE ANALYSIS OF 3S
100
102
102
110
111
113
114
119
119
119
120
120
144
144
146
CHAPTER 4 PALLADIUM-CATALYZED DIRECT ARYLATIONS OF
AZOLES WITH ARYL SILICON AND TIN REAGENTS
4.1 INTRODUCTION 148
4 .2 RESULTS AND DISCUSSION 153
4.2.1 OPTIMIZING THE CATALYTIC SYSTEM 153
IMAGE 5
4.2.2 SCOPE AND LIMITATIONS 156
4.2.3 MECHANISM 160
4.3 CONCLUSION 163
4.4 REFERENCES 163
4.5 E X P E R I M E N T AL SECTION I 6 ?
4.5.1 GENERAL 167
4.5.2 MATERIALS 167
4.5.3 PALLADIUM-CATALYZED DIRECT COUPLING OF AZOLES WITH TRIALKOXY-
(ARYL)SILANES 1 67
4.5.4 PALLADIUM-CATALYZED DIRECT COUPLING OF AZOLES WITH ALLYL-
TRIPHENYLSTANNANE
4.5.5 X-RAY CRYSTAL STRUCTURE ANALYSIS OF 5 178
CHAPTER 5 PALLADIUM-CATALYZED DEHYDROGENATIVE CROSS
COUPLINGS OF AZOLES
5.1 INTRODUCTION 18
5.2 RESULTS A ND DISCUSSION 183
5.2.1 SCOPE AND LIMITATIONS 183
5.2.2 MECHANISM 192
5.3 CONCLUSION M
5.4 REFERENCES I95
5.5 EXPERIMENTAL SECTION 199
5.5.1 GENERAL 1
5.5.2 MATERIALS 1
5.5.3 PRODUCTS FROM PALLADIUM-CATALYZED C -C COUPLINGS OF AZOLES 200
IMAGE 6
5.5.4 REACTIONS OF BENZOTHIAZOLE WITH ?RAW-[PHPDI(PPH 3 ) 2 ] 220
5.5.5 REACTION OF BENZOTHIAZOLE WITH 4,5-DIMETHYLTHIAZOLE WITHOUT AGF
222
5.5.6 PALLADIUM-CATALYZED REACTIONS OF AZOLES WITH [PH 2 I] + [PF 6 ]~
222
5.5.7 POWDER X-RAY DIFFRACTION ANALYSIS 223
5.5.8 X-RAY CRYSTAL STRUCTURE ANALYSIS 225
CHAPTER 6 PALLADIUM-CATALYZED DIRECT
TRIFLUOROMETHYLATION OF AZOLES VIA SP 2 C-H ACTIVATION
6.1 INTRODUCTION 229
6.2 RESULTS AND DISCUSSION 2 33
6.2.1 REACTION OPTIMIZATION 233
6.2.2 SUBSTRATE SCOPE 235
6.3 CONCLUSION 240
6.4 REFERENCES 240
6.5 E X P E R I M E N T AL SECTION 243
6.5.1 GENERAL 243
6.5.2 MATERIALS 243
6.5.3 GENERAL PROCEDURE FOR PALLADIUM-CATALYZED DIRECT
TRIFLUOROMETHYLATION OF AZOLES
6.5.4 PROCEDURE FOR THE PALLADIUM-CATALYZED DIRECT PENTA-
FLUOROETHYLATION OF 1 -METHYL-1 H-BENZIMIDAZOLE 2 52
6.5.5 PROCEDURE FOR THE REACTION BETWEEN COMPLEX TRANS-
[(PPH 3 ) 2 PHPDI] AND TRIFLUOROMETHYLTRIMETHYLSILANE 2 53
CURRICULUM VITAE 254
|
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| spelling | Han, Wei 1981- Verfasser (DE-588)1014033543 aut Iron and palladium catalyzed C-H functionalization von Wei Han 2011 254 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier München, Univ., Diss., 2011 (DE-588)4113937-9 Hochschulschrift gnd-content Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:19-131598 http://edoc.ub.uni-muenchen.de/13159/ Verlag kostenfrei Volltext https://nbn-resolving.org/urn:nbn:de:bvb:19-131598 Resolving-System DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=024421913&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Han, Wei 1981- Iron and palladium catalyzed C-H functionalization |
| subject_GND | (DE-588)4113937-9 |
| title | Iron and palladium catalyzed C-H functionalization |
| title_auth | Iron and palladium catalyzed C-H functionalization |
| title_exact_search | Iron and palladium catalyzed C-H functionalization |
| title_full | Iron and palladium catalyzed C-H functionalization von Wei Han |
| title_fullStr | Iron and palladium catalyzed C-H functionalization von Wei Han |
| title_full_unstemmed | Iron and palladium catalyzed C-H functionalization von Wei Han |
| title_short | Iron and palladium catalyzed C-H functionalization |
| title_sort | iron and palladium catalyzed c h functionalization |
| topic_facet | Hochschulschrift |
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