Organic letters

Electron Transfer Reduction of Nitriles Using SmI2–Et3N–H2O: Synthetic Utility and Mechanism

M Szostak, B Sautier, M Spain, DJ Procter

Index: Szostak, Michal; Sautier, Brice; Spain, Malcolm; Procter, David J. Organic Letters, 2014 , vol. 16, # 4 p. 1092 - 1095

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Citation Number: 21

Abstract

The first general reduction of nitriles to primary amines under single electron transfer conditions is demonstrated using SmI2 (Kagan's reagent) activated with Lewis bases. The reaction features excellent functional group tolerance and represents an attractive alternative to the use of pyrophoric alkali metal hydrides. Notably, the electron transfer from Sm (II) to CN functional groups generates imidoyl-type radicals from bench stable nitrile ...