Copper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides

Non‐activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper‐catalyzed cross‐coupling with aryl boron compounds and alkyl 9‐BBN reagents (see scheme; 9‐BBN=9‐borabicyclo[3.3.1]nonane). The reactions proceed with practically useful r...

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Published inAngewandte Chemie (International ed.) Vol. 50; no. 17; pp. 3904 - 3907
Main Authors Yang, Chu-Ting, Zhang, Zhen-Qi, Liu, Yu-Chen, Liu, Lei
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 18.04.2011
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
alkyl halides
alkyl pseudohalides
Boron Compounds - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
copper
Copper - chemistry
cross-coupling
Cross-Linking Reagents - chemistry
Hydrocarbons, Halogenated - chemistry
Molecular Structure
organoboron compounds
Physical Sciences
Science & Technology
alkyl pseudohalides
ROOM-TEMPERATURE
organoboron compounds
BETA-HYDROGENS
BROMIDES
NUCLEOPHILES
CU
alkyl halides
cross-coupling
CHLORIDES
copper
ARYL IODIDES
SUZUKI REACTIONS
ELECTROPHILES
GRIGNARD-REAGENTS
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Summary:Non‐activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper‐catalyzed cross‐coupling with aryl boron compounds and alkyl 9‐BBN reagents (see scheme; 9‐BBN=9‐borabicyclo[3.3.1]nonane). The reactions proceed with practically useful reactivities and thus complement palladium‐ and nickel‐catalyzed Suzuki–Miyaura coupling reactions of alkyl halides.
Bibliography:We are grateful for support in the form of national "973" grants from the Ministry of Science and Technology (No. 2011CB965300).
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Ministry of Science and Technology - No. 2011CB965300
ArticleID:ANIE201008007
We are grateful for support in the form of national “973” grants from the Ministry of Science and Technology (No. 2011CB965300).
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201008007