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A General Copper-Catalyzed Synthesis of Ynamides from 1,2-Dichloroenamides

Steven J. Mansfield, Russell C. Smith, Jonathan R. J. Yong, Olivia L. Garry, Edward A. Anderson*

*Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, U.K., Email: edward.andersonchem.ox.ac.uk

S. J. Mansfield, R. C. Smith, J. R. J. Yong, O. L. Garry, E. A. Anderson, Org. Lett., 2019, 21, 2918-2922.

DOI: 10.1021/acs.orglett.9b00971 (free Supporting Information)


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Abstract

A copper-catalyzed coupling of Grignard or organozinc nucleophiles with chloroynamides, formed in situ from 1,2-dichloroenamides, provides a broad range of ynamides. The reaction is readily scaled and overcomes typical limitations in ynamide synthesis such as the use of ureas, carbamates, and bulky or aromatic amide derivatives.

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Key Words

arylation, alkylation, sulfonamides


ID: J54-Y2019