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

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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.

see article for more examples

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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.

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Key Words

reduction of nitriles, samarium diiodide

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ID: J54-Y2014