Selective Synthesis of α,α-Dideuterio Alcohols by the Reduction of Carboxylic Acids Using SmI2 and D2O as Deuterium Source under SET Conditions

The first general method for the chemoselective synthesis of alpha,alpha-dideuterio alcohols directly from feedstock carboxylic acids under single electron transfer conditions using SmI2 is reported. This reaction proceeds after the activation of Sm(II) with a Lewis base, results in excellent levels of deuterium incorporation across a wide range of substrates, and represents an attractive alternative to processes mediated by pyrophoric alkali metal deuterides.