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

Tian Qin, Josep Cornella, Chao Li, Lara R Malins, Jacob T Edwards, Shuhei Kawamura, Brad D Maxwell, Martin D Eastgate, Phil S Baran

Index: Science 352(6287) , 801-5, (2016)

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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). Copyright © 2016, American Association for the Advancement of Science.