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

Michal Szostak*, Brice Sautier, Malcolm Spain and David J. Procter*

*School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, United Kingdom, Email: michal.szostakrutgers.edu, david.j.proctermanchester.ac.uk

M. Szostak, B. Sautier, M. Spain, D. J. Procter, Org. Lett., 2014, 16, 1092-1095.

DOI: 10.1021/ol403668e (free Supporting Information)


Abstract

Activation of SmI2 (Kagan’s reagent) with Lewis bases enables a mild general reduction of nitriles to primary amines under single electron transfer conditions. Activated samarium diiodide features excellent functional group tolerance and is therefore an attractive alternative to pyrophoric alkali metal hydrides. Notably, an electron transfer from Sm(II) to bench stable nitrile precursors generates imidoyl-type radicals.

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Highly Chemoselective Reduction of Amides (Primary, Secondary, Tertiary) to Alcohols using SmI2/Amine/H2O under Mild Conditions

M. Szostak, M. Spain, A. J. Eberhard, D. J. Procter, J. Am. Chem. Soc., 2014, 136, 2268-2271.


Key Words

reduction of nitrilessamarium diiodide


ID: J54-Y2014