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Cobalt-Catalyzed Asymmetric Sequential Hydroboration/Hydrogenation of Internal Alkynes

Jun Guo, Biao Cheng, Xuzhong Shen and Zhan Lu*

*Department of Chemistry, Zhejiang University, Hangzhou 310058, China, Email: luzhanzju.edu.cn

J. Guo, B. Cheng, X. Shen, Z. Lu, J. Am. Chem. Soc., 2017, 139, 15316-15319.

DOI: 10.1021/jacs.7b09832 (free Supporting Information)


Abstract

A chiral imidazoline iminopyridine (IIP) ligand enables a highly regio- and enantioselective cobalt-catalyzed hydroboration/hydrogenation of internal alkynes with HBpin in the presence of hydrogen. Primary mechanistic studies show that a cobalt-catalyzed regioselective hydroboration of alkynes is followed by a HBpin-promoted and cobalt-catalyzed enantioselective hydrogenation of alkenylboronates.

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proposed mechanism



Key Words

benzylboronates, hydrogen


ID: J48-Y2017