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A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents.

ABSTRACT: Alkyl carboxylic acids are ubiquitous in all facets of chemical science, from natural products to polymers, and represent an ideal starting material with which to forge new connections. This study demonstrates how the same activating principles used for decades to make simple C-N (amide) bonds from carboxylic acids with loss of water can be used to make C-C bonds through coupling with dialkylzinc reagents and loss of carbon dioxide. This disconnection strategy benefits from the use of a simple, inexpensive nickel catalyst and exhibits a remarkably broad scope across a range of substrates (>70 examples).

SUBMITTER: Qin T

PROVIDER: S-EPMC4867118 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents.

Qin Tian T Cornella Josep J Li Chao C Malins Lara R LR Edwards Jacob T JT Kawamura Shuhei S Maxwell Brad D BD Eastgate Martin D MD Baran Phil S PS

Science (New York, N.Y.) 20160421 6287

Alkyl carboxylic acids are ubiquitous in all facets of chemical science, from natural products to polymers, and represent an ideal starting material with which to forge new connections. This study demonstrates how the same activating principles used for decades to make simple C-N (amide) bonds from carboxylic acids with loss of water can be used to make C-C bonds through coupling with dialkylzinc reagents and loss of carbon dioxide. This disconnection strategy benefits from the use of a simple, ...[more]

PMID: 27103669

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