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

Michal Szostak*, Malcolm Spain , Andrew J. Eberhart 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, M. Spain, A. J. Eberhard, D. J. Procter, J. Am. Chem. Soc., 2014, 136, 2268-2271.

DOI: 10.1021/ja412578t

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Abstract

A highly chemoselective direct reduction of primary, secondary, and tertiary amides to alcohols in high yields in presence of SmI₂/amine/H₂O proceeds via C-N bond cleavage in a carbinolamine intermediate and shows excellent functional group tolerance. The expected C-O cleavage products are not formed under the reaction conditions. Notably, the method provides direct access to acyl-type radicals from unactivated amides under mild conditions.

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Pentafluorophenyl Esters: Highly Chemoselective Ketyl Precursors for the Synthesis of α,α-Dideuterio Alcohols Using SmI₂ and D₂O as a Deuterium Source

H. Li, Y. Hou, C. Liu, Z. Lai, L. Ning, R. Szostak, M. Szostak, J. An, Org. Lett., 2020, 22, 1249-1253.

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

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

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Key Words

reduction of amides, samarium diiodide

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ID: J48-Y2014