Facile, green, and functional group-tolerant reductions of carboxylic acids…in, or with, water†

Abstract

Facile reductions of carboxylic acids to aldehydes or alcohols can be effected under mild conditions upon initial conversion to their corresponding S-2-pyridyl thioesters. Upon treatment with a commercially available and air-stable nickel pre-catalyst and silane as a stoichiometric reductant, aldehydes are formed in moderate to good yields. Alternatively, the 1-pot conversion of acids to their thioester derivatives can be followed by reduction to the alcohol upon treatment with sodium borohydride. A variety of starting materials ranging from highly functionalized acids to educts from the Merck informer library can be transformed using these green reaction media.