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

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.

SUBMITTER: Villalobos JM

PROVIDER: S-EPMC2561227 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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

Villalobos Janette M JM Srogl Jiri J Liebeskind Lanny S LS

Journal of the American Chemical Society 20071130 51

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 ...[more]

PMID: 18047333

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