Oxidative cross-coupling reactions:
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| Main Authors: | , , , , , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH Verlag GmbH & Co. KGaA
[2017]
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | IX, 229 Seiten Illustrationen |
| ISBN: | 9783527336883 |
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MARC
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Record in the Search Index
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| adam_text | CONTENTS
1 OXIDATIVE COUPLING - BONDING BETWEEN TWO NUCLEOPHILES
1
1.1 INTRODUCTION/GENERAL 1
1.1.1 WHAT IS OXIDATIVE CROSS-COUPLING? 1
1.1.2 WHY OXIDATIVE CROSS-COUPLING? 1
1.1.3 HOW DOES OXIDATIVE CROSS-COUPLING WORK? 3
1.1.4 DEVELOPMENT AND OUTLOOK 4
REFERENCES 4
2 ORGANOMETALS AS NUCLEOPHILES 7
2.1 CLASSIFICATION AND APPLICATIONS OF ORGANOMETALLIC REAGENTS
2.2 CSP-M AND CSP-M AS NUCLEOPHILES 8
2.2.1 ALKYNE-ALKYNE OXIDATIVE COUPLING 9
2.2.1.1 ALKYNYL-SI 11
2.2.1.2 ALKYNYL-SN 12
2.2.1.3 ALKYNYL-B 14
2.2.1.4 ALKYNYL-MG 17
2.2.1.5 ALKYNYL-TE 19
2.2.2 ALKYNE-CYANO OXIDATIVE COUPLING 22
2.3 CSP-M AND CSP2-M AS NUCLEOPHILES 22
2.4 CSP-M AND CSP3-M AS NUCLEOPHILES 28
2.5 CSP2-M AND CSP2-M AS NUCLEOPHILES 30
2.5.1 HOMOCOUPLING OF CSP2-M 30
2.5.2 CROSS-COUPLING BETWEEN DIFFERENT SPECIES OF CSP2-M 32
2.6 CSP2-M AND CSP3-M AS NUCLEOPHILES 34
2.7 CSP3-M AND CSP3-M AS NUCLEOPHILES 37
2.8 CONCLUSIONS 40
ACKNOWLEDGMENTS 41
REFERENCES 42
3 OXIDATIVE COUPLINGS INVOLVING THE CLEAVAGE OF C-H BONDS 45
3.1 THEORETICAL UNDERSTANDINGS AND METHODS IN C-H BOND
FUNCTIONALIZATION 45
3.1.1 INTRODUCTION 45
3.1.2 MECHANISMS OF C-H CLEAVAGE BY TRANSITION METALS 47
3.1.2.1 OXIDATIVE ADDITION 49
3.1.2.2 ELECTROPHILIC SUBSTITUTION 49
3.1.2.3 O-BOND METATHESIS 52
3.1.2.4 CONCERTED METALATION DEPROTONATION (CMD) 52
3.1.2.5 1,2-ADDITION 55
3.1.2.6 BIOMIMETIC C-H OXIDATION 55
3.1.2.7 CARBENOID/NITRENOID C-H INSERTION 56
3.1.3 METHODS FOR SELECTIVE C-H BOND FUNCTIONALIZATION 58
3.1.3.1 DIRECTED C-H FUNCTIONALIZATION 58
3.1.3.2 STERICALLY CONTROLLED C-H FUNCTIONALIZATION 63
3.1.3.3 C-H FUNCTIONALIZATION VIA IONIC INTERMEDIATES 63
3.1.3.4 C -H FUNCTIONALIZATION VIA RADICAL INTERMEDIATES 67
3.2 OXIDATIVE COUPLINGS BETWEEN ORGANOMETALS AND HYDROCARBONS 71
3.2.1 C(SP)-H AND ORGANOMETALS AS NUCLEOPHILES 71
3.2.2 CSP2-H AND ORGANOMETALS AS NUCLEOPHILES 73
3.2.3 CSP3-H AND ORGANOMETALS AS NUCLEOPHILES 93
3.3 OXIDATIVE COUPLINGS BETWEEN TWO HYDROCARBONS 95
3.3.1 C(SP)-H AND C(SP)-H AS NUCLEOPHILES 95
3.3.2 C(SP)-H AND C(SP2)-H AS NUCLEOPHILES 99
3.3.3 C(SP)-H AND C(SP3)-H AS NUCLEOPHILES 105
3.3.4 CSP2-H AND CSP2-H AS NUCLEOPHILES 106
3.3.4.1 OXIDATIVE COUPLING BETWEEN DIRECTING-GROUP-CONTAINING ARENES
AND UNACTIVATED ARENES 107
3.3.4.2 OXIDATIVE COUPLING OF ARENES WITHOUT DIRECTING GROUPS 109
3.3.4.3 INTRAMOLECULAR OXIDATIVE COUPLING OF UNACTIVATED ARENES 110
3.3.4.4 OXIDATIVE HECK-TYPE CROSS-COUPLING 114
3.3.5 CSP2-H AND CSP3-H AS NUCLEOPHILES 123
3.3.5.1 INTRAMOLECULAR OXIDATIVE COUPLING BETWEEN AROMATIC CSP2-H AND
CSP3-H 123
3.3.5.2 INTRAMOLECULAR OXIDATIVE COUPLING BETWEEN ALLCENE CSP2-H AND
CSP3-H 125
3.3.5.3 INTERMOLECULAR OXIDATIVE COUPLING BETWEEN CSP2-H AND
CSP3-H 127
3.3.6 C(SP3)-H AND C(SP3)-H AS NUCLEOPHILES 128
3.4 CONCLUSIONS 130
REFERENCES 130
4 BONDING INCLUDING HETEROATOMS VIA OXIDATIVE COUPLING 139
4.1 INTRODUCTION 139
4.2 OXIDATIVE C-O BOND FORMATION 140
4.2.1 C-H AND O-M AS NUCLEOPHILES 140
4.2.2 C-H AND O-H AS NUCLEOPHILES 140
4.2.2.1 C(SP2, ARYL)-0 BOND FORMATION 140
4.2.2.2 C(SP2, HETEROARYL, ALKENYL)-0 BOND FORMATION 144
4
.
2.23 C(SP3, BENZYL)-0 BOND FORMATION 145
4.2.2.4 C(SP3, ALKANES WITH DIRECTING GROUP)-0 BOND FORMATION 145
4.2.2.5 C(SP3, ETHERS, AMINES, AMIDES, ALKANES)-0 BOND FORMATION 148
4.2.2.6 C(SP3, ALLYL)-0 BOND FORMATION 148
4.3 OXIDATIVE C-N BOND FORMATION 152
4.3.1 C(SP)-N BOND FORMATION 152
4.3.2 C(SP2, ARENES WITH DIRECTING GROUP)-N BOND FORMATION 153
4.3.3 C(SP2, SIMPLE ARENES)-N BOND FORMATION 156
4.3.4 C(SP2, HETEROARYL)-N BOND FORMATION 156
4.3.5 C(SP2, ALKENYL)-N BOND FORMATION 159
4.3.6 C(SP3, ALKYL)-N BOND FORMATION 163
4.3.7 C(SP3, ALLYL)-N BOND FORMATION 164
4.4 OXIDATIVE C-HALO BOND FORMATION 166
4.4.1 C-H AND HALO-H AS NUCLEOPHILES 167
4.4.2 C-H AND HALO-M AS NUCLEOPHILES 168
4.5 OXIDATIVE C-S BOND FORMATION 170
4.5.1 C(SP2)-S BOND FORMATION 170
4.5.2 C(SP)-S BOND FORMATION 171
4.6 OXIDATIVE C-P BOND FORMATION 172
4.6.1 C(SP2, ARYL)-P BOND FORMATION 172
4.6.2 C(SP2, HETEROARYL)-P BOND FORMATION 173
4.6.3 C(SP2, ALKENYL)-P BOND FORMATION 176
4.6.4 C(SP)-P BOND FORMATION 176
4.6.5 C(SP3)-P BOND FORMATION 176
4.7 OXIDATIVE C-B BOND FORMATION 177
REFERENCES 178
5 OXIDATIVE RADICAL COUPLINGS 185
5.1 INTRODUCTION 185
5.2 OXIDATIVE RADICAL C-C COUPLINGS 185
5.2.1 COUPLING OF CSP3-H WITH CSP-H BONDS 185
5.2.2 COUPLING OF CSP3-H WITH CSP2-H BONDS 187
5.2.3 COUPLING OF CSP3-H WITH CSP3-H BONDS 200
5.2.4 COUPLING OF CSP2-H WITH CSP2-H BONDS 204
5.3 OXIDATIVE RADICAL C-C COUPLINGS THROUGH CASCADE PROCESS 208
5.4 OXIDATIVE RADICAL C-C COUPLINGS VIA C-C(N) BOND CLEAVAGE 22 7
REFERENCES 222
INDEX
225
|
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| author | Lei, Aiwen Shi, Wei Liu, Chao Liu, Wei 1979- Zhang, Hua He, Chuan |
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| author_facet | Lei, Aiwen Shi, Wei Liu, Chao Liu, Wei 1979- Zhang, Hua He, Chuan |
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| discipline | Chemie / Pharmazie |
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| illustrated | Illustrated |
| indexdate | 2024-07-10T07:36:27Z |
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| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-029249400 |
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| physical | IX, 229 Seiten Illustrationen |
| publishDate | 2017 |
| publishDateSearch | 2017 |
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| publisher | Wiley-VCH Verlag GmbH & Co. KGaA |
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| spelling | Lei, Aiwen Verfasser (DE-588)1117094189 aut Oxidative cross-coupling reactions Aiwen Lei, Wei Shi, Chao Liu, Wei Liu, Hua Zhang, and Chuan He Weinheim Wiley-VCH Verlag GmbH & Co. KGaA [2017] © 2017 IX, 229 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier Oxidative Kupplungsreaktion (DE-588)4308475-8 gnd rswk-swf Kreuzkupplungsreaktion (DE-588)1033635499 gnd rswk-swf Catalysis Chemie Chemistry Katalyse Nachhaltige u. Grüne Chemie Organic Chemistry Organische Chemie Sustainable Chemistry & Green Chemistry Kreuzkupplungsreaktion (DE-588)1033635499 s Oxidative Kupplungsreaktion (DE-588)4308475-8 s DE-604 Shi, Wei Verfasser (DE-588)1117095223 aut Liu, Chao Verfasser (DE-588)1117101525 aut Liu, Wei 1979- Verfasser (DE-588)1017342369 aut Zhang, Hua Verfasser (DE-588)1117102025 aut He, Chuan Verfasser (DE-588)1117103005 aut Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, ePDF 978-3-527-68101-3 Erscheint auch als Online-Ausgabe, ePub 978-3-527-68100-6 Erscheint auch als Online-Ausgabe, Mobi 978-3-527-68099-3 Erscheint auch als Online-Ausgabe, oBook 978-3-527-68098-6 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029249400&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Lei, Aiwen Shi, Wei Liu, Chao Liu, Wei 1979- Zhang, Hua He, Chuan Oxidative cross-coupling reactions Oxidative Kupplungsreaktion (DE-588)4308475-8 gnd Kreuzkupplungsreaktion (DE-588)1033635499 gnd |
| subject_GND | (DE-588)4308475-8 (DE-588)1033635499 |
| title | Oxidative cross-coupling reactions |
| title_auth | Oxidative cross-coupling reactions |
| title_exact_search | Oxidative cross-coupling reactions |
| title_full | Oxidative cross-coupling reactions Aiwen Lei, Wei Shi, Chao Liu, Wei Liu, Hua Zhang, and Chuan He |
| title_fullStr | Oxidative cross-coupling reactions Aiwen Lei, Wei Shi, Chao Liu, Wei Liu, Hua Zhang, and Chuan He |
| title_full_unstemmed | Oxidative cross-coupling reactions Aiwen Lei, Wei Shi, Chao Liu, Wei Liu, Hua Zhang, and Chuan He |
| title_short | Oxidative cross-coupling reactions |
| title_sort | oxidative cross coupling reactions |
| topic | Oxidative Kupplungsreaktion (DE-588)4308475-8 gnd Kreuzkupplungsreaktion (DE-588)1033635499 gnd |
| topic_facet | Oxidative Kupplungsreaktion Kreuzkupplungsreaktion |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029249400&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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