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Copper(II)-Catalyzed Selective Hydroboration of Ketones and Aldehydes

Haisu Zeng, Jing Wu, Sihan Li, Christina Hui, Anita Ta, Shu-Yuan Cheng*, Shengping Zheng*, Guoqi Zhang*

*John Jay College & The Graduate Center of the City University of New York, New York, New York 10019; Hunter College, CUNY, New York 10065, United States, Email: shchengjjay.cuny.edu, szh0007hunter.cuny.edu, guzhangjjay.cuny.edu

H. Zeng, J. Wu, S. Li, C. Hui, A. Ta, S.-Y. Cheng, S. Zheng, G. Zhang, Org. Lett., 2019, 21, 401-406.

DOI: 10.1021/acs.orglett.8b03583

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Abstract

A nonanuclear copper(II) complex obtained by a facile one-pot self-assembly catalyzes the hydroboration of ketones and aldehydes with the absence of an activator under mild, solvent-free conditions. The air- and moisture-stable catalyst displays high efficiency and chemoselectivity on aldehydes over ketones and ketones over imines.

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ball-stick representation of the coordination cluster Cu9(L)2(CH3COO-)8(CH3OH)2(μ3-OH)4

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Key Words

reduction of carbonyl compounds, pinacolborane

ID: J54-Y2019