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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 929-939

Nickel-catalyzed coupling reactions of alkenes

Sze-Sze Ng, Chun-Yu Ho, Kristin D. Schleicher and Timothy F. Jamison

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA

Abstract: Several reactions of simple, unactivated alkenes with electrophiles under Ni(0) catalysis are discussed. The coupling of olefins with aldehydes and silyl triflates provides allylic or homoallylic alcohol derivatives, depending on the supporting ligands and, to a lesser extent, the substrates employed. Reaction of alkenes with isocyanates yields N-alkyl acrylamides. In these methods, alkenes act as the functional equivalents of alkenyl- and allylmetal reagents.