Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters
Patrick J Moon1, Anis Fahandej-Sadi1, Wenyu Qian1
1Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.
Abstract:
The copper-catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron-deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.
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