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. 2007 Dec 26;129(51):15734-5.
doi: 10.1021/ja074931n. Epub 2007 Nov 30.

A new paradigm for carbon-carbon bond formation: aerobic, copper-templated cross-coupling

Janette M Villalobos  1 , Jiri Srogl, Lanny S Liebeskind
Affiliations

A new paradigm for carbon-carbon bond formation: aerobic, copper-templated cross-coupling

Janette M Villalobos et al. J Am Chem Soc. .

Abstract

Thiol esters and boronic acids react to produce ketones under aerobic conditions in the presence of catalytic quantities of a CuI or CuII salt. The reaction occurs at reasonable rates between room temperature and 50 degrees C at neutral pH using thiol esters derived from bulky 2 degrees amides of thiosalicylamides such as those based on N-tert-butyl-2-mercaptobenzamide. In this mechanistically unprecedented reaction system, the carbon-carbon bond formation occurs through templating of the thiol ester and the boronic acid at copper; the system is rendered catalytic in copper under the aerobic conditions.

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Figures

Scheme 1
Scheme 1
Proposed Mechanism
See this image and copyright information in PMC

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