Development of a Modified Bouveault-Blanc Reduction for the Selective Synthesis of α,α-Dideuterio Alcohols

A modified Bouveault Blanc reduction has been developed for the synthesis of alpha,alpha-dideuterio alcohols from carboxylic acid esters. Sodium dispersions are used as the electron donor in this electron transfer reaction, and ethanol -d(1), is employed as the deuterium source. This reaction uses stable, a a cheap, and commercially available reagents, is operationally simple, and results in excellent deuterium incorporation across a broad range of aliphatic esters, which provides an attractive, alternative to reactions mediated by expensive pyrophoric alkali metal deuterides.