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 (free Supporting Information)
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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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H. Li, Y. Hou, C. Liu, Z. Lai, L. Ning, R. Szostak, M. Szostak, J. An, Org. Lett., 2020, 22, 1249-1253.
M. Szostak, B. Sautier, M. Spain, D. J. Procter, Org. Lett., 2014, 16, 1092-1095.