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

Organic Letters 9(5), 875-878, DOI: 10.1021/ol063111x

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