Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 51, Pages 15734-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja074931n
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Funding
- NIGMS NIH HHS [GM066153, R01 GM066153-19A1, R01 GM066153] Funding Source: Medline
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Thiol esters and boronic acids react to produce ketones under aerobic conditions in the presence of catalytic quantities of a Cu-I or Cu-II 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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