A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents.
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).
Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Tian
T
Qin
Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Josep
J
Cornella
Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Chao
C
Li
Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Lara R
LR
Malins
Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Jacob T
JT
Edwards
Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Shuhei
S
Kawamura
Discovery Chemistry Platforms-Radiochemistry, Bristol-Myers Squibb, Post Office Box 4000, Princeton, NJ, USA.
Brad D
BD
Maxwell
Chemical Development, Bristol-Myers Squibb, One Squibb Drive, New Brunswick, NJ 08903, USA.
Martin D
MD
Eastgate
Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. pbaran@scripps.edu.
Phil S
PS
Baran