Copper-Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates |
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| Authors: | Tao He Bin Li Li-Chuan Liu Jing Wang Wen-Peng Ma Guang-Yu Li Prof?Dr Qing-Wei Zhang Prof?Dr Wei He |
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| Institution: | 1. MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084 P. R. China;2. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai, 200032 P. R. China;3. Department of Chemistry, University of Science and Technology of China, Hefei, 230026 P. R. China |
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| 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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| Keywords: | alkynes bis-borylation copper oxindoles trifunctionalization |
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