New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation:
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| Main Author: | |
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| Format: | Thesis Book |
| Language: | English |
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Singapore
Springer
[2017]
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| Series: | Springer Theses
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| Subjects: | |
| Online Access: | Inhaltsverzeichnis Klappentext |
| Physical Description: | xvii, 216 Seiten Illustrationen |
| ISBN: | 9789811031922 |
| ISSN: | 2190-5053 |
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| 245 | 1 | 0 | |a New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation |c Rui Shang |
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| adam_text | Contents
Part I New Carbon—Carbon Coupling Reactions Based
on Decarboxylation
1 Transition Metal-Catalyzed Decarboxylation
and Decarboxylative Cross-Couplings.............................. 3
1.1 Introduction................................................... 3
1.2 Metal-Catalyzed Decarboxylation Reactions...................... 4
1.2.1 Cu-Catalyzed Protodecarboxylation...................... 4
1.2.2 Ag-Catalyzed Protodecarboxylation...................... 4
1.2.3 Au-Catalyzed Protodecarboxylation...................... 5
1.2.4 Pd-Catalyzed Protodecarboxylation...................... 6
1.2.5 Rh-Catalyzed Protodecarboxylation...................... 6
1.3 Decarboxylative C—C Cross-Coupling Reactions................... 7
1.3.1 Cross-Coupling Between C—COOH and C—X Bonds ... 7
1.3.2 Decarboxylative Heck Couplings........................ 19
1.3.3 Decarboxylative Cross-Coupling of Activated
C-H/C-COOH............................................ 23
1.3.4 Cross-Coupling Between C-COOH and C—M Bonds ... 32
1.4 Decarboxylative Carbon—Heteroatom Cross-Coupling.............. 34
1.4.1 Decarboxylative C—N Cross-Coupling.................... 34
1.4.2 Decarboxylative C—S Cross-Coupling.................... 34
1.4.3 Decarboxylative C—P Cross-Coupling.................... 35
1.4.4 Decarboxylative C-Halide Cross-Coupling............... 36
1.5 Decarboxylative Addition Reactions............................ 36
1.5.1 Additions to Aldehydes and Iminės..................... 36
1.5.2 Additions to Alkynes.................................. 38
1.5.3 Additions to Nitriles................................. 39
1.5.4 1,4-Additions......................................... 39
XIII
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1.6 Other Intramolecular Decarboxylative Coupling Reactions
1.6.1 Decarboxylative Coupling Reaction of Allyl
Carboxylates ..................................
1.6.2 Intramolecular Decarboxylative Cyclization.....
1.7 Application of Decarboxylative Coupling Method
in the Synthesis of Important Molecules................
1.8 Conclusions and Perspectives...........................
References...................................................
Palladium-Catalyzed Decarboxylative Coupling of Potassium
Oxalate Monoester with Aryl and Alkenyl Halides..............
2.1 Introduction........................................
2.2 Results and Discussion.................................
2.2.1 Investigation of the Reaction Conditions.......
2.2.2 Exploration of the Substrate Scope.............
2.2.3 Mechanistic Study..............................
2.3 Conclusion.............................................
2.4 Experimental Section and Compound Data.................
2.4.1 General Information............................
2.4.2 Experimental Procedure.........................
2.4.3 Characterization of the Products ..............
References...................................................
Synthesis of Polyfluorobiaryls via Copper-Catalyzed
Decarboxylative Couplings of Potassium Polyfluorobenzoates
with Aryl Bromides and Iodides...............................
3.1 Introduction......................................
3.2 Results and Discussion. . .............................
3.2.1 Investigation of Reaction Condition............
3.2.2 Exploration of the Substrate Scope.............
3.2.3 Mechanistic Study..............................
3.3 Conclusión.............................................
3.4 Experimental Section and Compound Data.................
3.4.1 General Information. . ........................
3.4.2 General Procedure..............................
3.4.3 Characterization of the Products...............
References. . ...............................................
Palladium-Catalyzed Decarboxylative Couplings
of Potassium Polyfluorobenzoates with Aryl Bromides,
Chlorides, and Triflates.....................................
4.1 Introduction ..........................................
4.1.1 Investigation of the Reaction Conditions.......
4.1.2 Exploration of the Substrate Scope.............
4.1.3 Mechanistic Study..............................
4.1.4 The Cross-Coupling Controlled by the Ligands. .
Contents
XV
4.2 Conclusion..................................................... 86
4.3 Experimental Section and Compound Data......................... 86
4.3.1 General Information.................................... 86
4.3.2 General Procedures..................................... 87
4.3.3 Characterization of the Products....................... 88
References........................................................... 92
5 Construction of C(sp3)-C(sp2) Bonds Via Palladium-Catalyzed
Decarboxylative Couplings of 2-(2-Azaaryl)Acetate Salts
with Aryl Halides.................................................... 95
5.1 Introduction................................................... 95
5.2 Results and Discussion......................................... 96
5.2.1 Investigation of the Reaction Conditions............... 96
5.2.2 Exploration of the Substrate Scope..................... 97
5.2.3 Mechanistic Study...................................... 98
5.3 Conclusion.................................................... 100
5.4 Experimental Section and Compound Data........................ 100
5.4.1 General Information................................... 100
5.4.2 General Procedure..................................... 101
5.4.3 Characterization of the Products...................... 101
References.......................................................... 104
6 Synthesis of a-Aryl Nitriles and a-Aryl Acetate Esters Via
Palladium-Catalyzed Decarboxylative Couplings of a-Cyano
Aliphatic Carboxylate Salts and Malonate Monoester Salts with
Aryl Halides........................................................ 107
6.1 Introduction.................................................. 107
6.2 Results and Discussion........................................ 110
6.2.1 Investigation of the Reaction Conditions.............. 110
6.2.2 Exploration of the Substrate Scope.................... 112
6.2.3 Application of the Method............................. 116
6.2.4 Extending the Concept of Decarboxylative
a-Arylation to the Synthesis of a-Aryl Acetates..... 117
6.3 Conclusion.................................................... 11S
6.4 Experiment Section and Compound Data.......................... 119
6.4.1 General Information................................... 119
6.4.2 General Procedures.................................... 119
6.4.3 Characterization of the Products...................... 120
References.......................................................... 123
7 Palladium-Catalyzed Decarboxylative Couplings of Nitrophenyl
Acetate Salts and Its Derivatives with Aryl Halides................. 125
7.1 Introduction.................................................. 125
7.2 Results and Discussion........................................ 126
7.2.1 Investigation of the Reaction Conditions.............. 126
7.2.2 Exploration of Substrate Scope........................ 127
XVI
Contents
7.2.3 Application of the Reaction in Synthesis of 4-Aryl
Quinolines and Dihydroquinolinones................... 129
7.2.4 Transformation of ֊NO2 by Sandmeyer Reaction......... 129
7.3 Conclusion................................................... 131
7.4 Experimental Section and Compound Data........................ 132
7.4.1 General Information................................... 132
7.4.2 General Procedures , . ............................... 132
7.4.3 Characterization of the Products...................... 135
References........................................................ 138
8 Palladium-Catalyzed Decarboxylative Benzylation of a-Cyano
Aliphatic Carboxylate Salts with Benzyl Electrophiles.............. 141
8.1 Introduction ............................................... 141
8.2 Results and Disscussion....................................... 142
8.2.1 Investigation of the Reaction Conditions.............. 142
8.2.2 Study of the Substrate Scope.......................... 144
8.2.3 Proposed Reaction Mechanism........................... 148
8.3 Conclusion.................................................... 149
8.4 Experimental Section and Compound Data........................ 150
8.4.1 General Information.................................. 150
8.4.2 Experimental Procedure................................ 150
8.4.3 Characterization of the Products...................... 153
References.......................................................... 157
Part II New Carbon-Carbon Coupling Reactions Based
on Iron-Catalyzed C-H Activation
9 Recent Developments of Iron-Catalyzed Directed C-H
Activation/C-C Bond Formation Reactions........................... 161
9.1 Introduction................................................. 161
9.2 Iron-Catalyzed Direct Arylation of the C-H Bonds with Aryl
Halides as the Arylation Reagents . .......................... 162
9.3 Iron-Catalyzed Direct Activation of C-H Bond Using
Organometallic Reagents..................................... 165
References......................................................... 173
10 P-Arylation of Carboxamides Via Iron-Catalyzed
C(sp3)-H Bond Activation............................................ 175
10.1 Introduction............................................... 175
10.2 Results and Discussion....................................... 177
10.2.1 Investigation of the Reaction Conditions. ............ 177
10.2.2 Exploration of the Substrate Scope.................... 178
10.2.3 Deuterated Experiments................................ 180
10.3 Conclusion.................................................... 181
Contents xvii
10.4 Experimental Section and Compound Data..................... 181
10.4.1 General Information.................................. 181
10.4.2 Investigation of the Key Reaction Parameters......... 182
10.4.3 Characterization of Compounds........................ 185
10.4.4 Deuterium-Labeling and KIE Experiments............... 191
References.......................................................... 195
11 Iron-Catalyzed Directed C(sp2)-H Bond Functionalization with
Organoboron Compounds............................................... 197
11.1 Introduction.................................................. 197
11.2 Results and Discussion........................................ 199
11.2.1 Investigation of the Reaction Conditions............. 199
11.2.2 Exploration of the Substrate Scope................... 201
11.2.3 Mechanistic Study.................................... 204
11.3 Conclusion.................................................... 206
11.4 Experimental Section and Compound Data..................... 206
11.4.1 General Information.................................. 206
11.4.2 Experimental Procedures.............................. 207
References.......................................................... 215
This thesis presents the latest developments in new catalytic C-C bond
formation methods using easily accessible carboxylate salts through catalytic
decarboxylation with good atom economy, and employing the sustainable
element iron as the catalyst to directly activate C-H bonds with high step
efficiency. In this regard, it explores a mechanistic understanding of the newly
discovered decarboxylative couplings and the catalytic reactivity of the iron
catalyst with the help of density functional theory calculation.
The thesis is divided into two parts, the first of which focuses on the
development of a series of previously unexplored, inexpensive carboxylate salts
as useful building blocks for the formation of various C-C bonds to access
valuable chemicals. In turn, the second part is devoted to several new C-C
bond formation methodologies using the most ubiquitous transition metal,
iron, as a catalyst, and using the ubiquitous C-H bond as the coupling partner.
|
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| spelling | Shang, Rui Verfasser aut New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation Rui Shang Singapore Springer [2017] xvii, 216 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier Springer Theses 2190-5053 Dissertation University of Science and Technology of China, Hefei, China Chemistry Organometallic chemistry Chemistry, Physical and theoretical Catalysis Organometallic Chemistry Theoretical and Computational Chemistry Chemie Katalyse (DE-588)4029921-1 gnd rswk-swf Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 gnd rswk-swf Eisen (DE-588)4014002-7 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 s Eisen (DE-588)4014002-7 s Katalyse (DE-588)4029921-1 s DE-604 Erscheint auch als Online-Ausgabe 978-981-10-3193-9 Digitalisierung UB Regensburg - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029949060&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Regensburg - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029949060&sequence=000002&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext |
| spellingShingle | Shang, Rui New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation Chemistry Organometallic chemistry Chemistry, Physical and theoretical Catalysis Organometallic Chemistry Theoretical and Computational Chemistry Chemie Katalyse (DE-588)4029921-1 gnd Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 gnd Eisen (DE-588)4014002-7 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4164549-2 (DE-588)4014002-7 (DE-588)4113937-9 |
| title | New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation |
| title_auth | New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation |
| title_exact_search | New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation |
| title_full | New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation Rui Shang |
| title_fullStr | New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation Rui Shang |
| title_full_unstemmed | New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation Rui Shang |
| title_short | New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation |
| title_sort | new carbon carbon coupling reactions based on decarboxylation and iron catalyzed c h activation |
| topic | Chemistry Organometallic chemistry Chemistry, Physical and theoretical Catalysis Organometallic Chemistry Theoretical and Computational Chemistry Chemie Katalyse (DE-588)4029921-1 gnd Kohlenstoff-Kohlenstoff-Bindung (DE-588)4164549-2 gnd Eisen (DE-588)4014002-7 gnd |
| topic_facet | Chemistry Organometallic chemistry Chemistry, Physical and theoretical Catalysis Organometallic Chemistry Theoretical and Computational Chemistry Chemie Katalyse Kohlenstoff-Kohlenstoff-Bindung Eisen Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029949060&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029949060&sequence=000002&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
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