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Nickel-Catalyzed Synthesis of Acrylamides from α-Olefins and Isocyanates

Kristin D. Schleicher and Timothy F. Jamison*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: tfjmit.edu

K. D. Schleicher, T. F. Jamison, Org. Lett., 2007, 9, 875-878.

DOI: 10.1021/ol063111x (free Supporting Information)


Abstract

A nickel(0)-catalyzed coupling of α-olefins and isocyanates in the presence of an N-heterocyclic carbene ligand proceeds preferentially at the 2-position of the olefin to provide α,β-unsaturated amides. N-tert-butyl amide products can be converted to the corresponding primary amides under acidic conditions.

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Key Words

α,β-unsaturated amides


ID: J54-Y2007-0770