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Nickel-Catalyzed Reduction of Secondary and Tertiary Amides

Bryan J. Simmons, Marie Hoffmann, Jaeyeon Hwang, Moritz K. Jackl and Neil K. Garg*

*Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States, Email: neilgargchem.ucla.edu

B. J. Simmons, M. Hoffmann, J. Hwang, M. K. Jackl, N. K. Garg, Org. Lett., 2017, 19, 1910-1913.

DOI: 10.1021/acs.orglett.7b00683 (free Supporting Information)


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Abstract

A nickel-catalyzed reduction of secondary and tertiary amides provides amines. The reaction transforms various amide substrates, proceeds in the presence of esters and epimerizable stereocenters, and can be used to achieve the reduction of lactams. Moreover, this methodology provides a simple tactic for accessing medicinally relevant α-deuterated amines.

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Key Words

reduction of amides, phenylsilane


ID: J54-Y2017