Zn-Catalyzed Regioselective and Chemoselective Reduction of Aldehydes, Ketones and Imines
Miaomiao Zhang1, Hongmei Jiao1, Haojie Ma1
1Laboratory of New Energy & New Functional Materials, Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an 716000, China.
Abstract:
An operationally convenient Zn-catalyzed synthesis of alcohols by the reduction of aldehydes, ketones, and α,β-unsaturated aldehydes/ketones is reported. It is a rare example of using mild and sustainable HBpin as a reductant for catalytic reduction of carbonyl compounds in the absence of acid or base as hydrolysis reagent. The reaction is upscalable and proceeds in high selectivity without the formation of boronate ester by-products, and tolerates sensitive functionalities, such as iodo, bromo, chloro, fluoro, nitro, trifluoromethyl, aminomethyl, alkynyl, and amide. The Zn(OAc)2/HBpin combination has been also proved to be chemoselective for the C=N reduction of imine analogs.
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