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

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Science  13 May 2016:
Vol. 352, Issue 6287, pp. 801-805
DOI: 10.1126/science.aaf6123

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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 CO2. The ready availability of numerous carboxylic acids (which are easily converted to esters) contributes to the reaction's versatility.

Science, this issue p. 801

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).

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