Zn-Catalyzed Regioselective and Chemoselective Reduction of Aldehydes, Ketones and Imines

An operationally convenient Zn-catalyzed synthesis of alcohols by the reduction of aldehydes, ketones, and alpha,beta-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.