Nickel-catalyzed cross-coupling of alkyl zinc halides for the formation of C(sp2)-C(sp3) bonds: Scope and mechanism

Abstract

Optimal conditions for a general Ni-catalysed Negishi cross-coupling of alkyl zinc halides with aryl, heteroaryl and alkenyl halides have been determined. These conditions allow the reaction to take place smoothly, with low catalyst loading, and in the presence of a wide variety of functional groups to afford products in good yields at room temperature. DFT studies on the mechanism support the occurrence of a catalytic cycle involving transmetalation of the alkyl zinc halide to Ni1 followed by oxidative addition of the haloarene and C-C reductive elimination. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.