Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using SmI2 and D2O as deuterium source under SET conditions.

Michal Szostak, Malcolm Spain, David J Procter

Index: Org. Lett. 16(19) , 5052-5, (2014)

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Abstract

The first general method for the chemoselective synthesis of α,α-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.