A New Paradigm for Carbon−Carbon Bond Formation:  Aerobic, Copper-Templated Cross-Coupling

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 °C at neutral pH using thiol esters derived from bulky 2° amides of thiosalicylamide...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2007-12, Vol.129 (51), p.15734-15735
Main Authors: Villalobos, Janette M, Srogl, Jiri, Liebeskind, Lanny S
Format: Article
Language:English
Subjects:
Benzamides - chemistry
Carbon - chemistry
Catalysis
Copper - chemistry
Hydrogen-Ion Concentration
Kinetics
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Summary: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 °C at neutral pH using thiol esters derived from bulky 2° 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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja074931n