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

Author:

Qin Tian1,Cornella Josep1,Li Chao1,Malins Lara R.1,Edwards Jacob T.1,Kawamura Shuhei1,Maxwell Brad D.2,Eastgate Martin D.3,Baran Phil S.1

Affiliation:

1. Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.

2. Discovery Chemistry Platforms–Radiochemistry, Bristol-Myers Squibb, Post Office Box 4000, Princeton, NJ, USA.

3. Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, NJ 08903, USA.

Abstract

Carbon links without helpful neighbors It's an irony of modern organic chemistry that the simplest-looking carbon-carbon bonds are often the hardest to make. Most reactions owe their efficiency to neighboring double bonds or oxygen and nitrogen atoms that linger in the products. Qin et al. now present a broadly applicable protocol for making C-C bonds in the absence of such surrounding help. The nickel-catalyzed process couples a zinc-activated carbon center to an ester that's poised to lose CO 2 . The ready availability of numerous carboxylic acids (which are easily converted to esters) contributes to the reaction's versatility. Science , this issue p. 801

Funder

Bristol-Myers Squibb

Catalan Government

U.S. Department of Defense

NIH

China Scholarship Council

National Institute of General Medical Sciences

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

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