Copper-Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates
Tao He1, Bin Li1, Li-Chuan Liu1
1MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084, P. R. China.
Abstract:
A copper-catalyzed trifunctionalization of alkynes that provides rapid access to oxindoles bearing a geminal diboronate side chain, highlighted by the simultaneous formation of one C-C bond and two C-B bonds, is reported. This new reaction features simple reaction conditions (ligand-free catalysis), a general substrate scope, and excellent chemoselectivity. Mechanistic study revealed a reaction sequence constituted by, in the order, borylation, intramolecular cross-coupling, hydroboration, which has been rarely documented.
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