An Efficient Nickel-Catalyzed Cross-Coupling Between sp3 Carbon Centers

Since the pioneering work of Wurtz, cross-couplings between sp³ carbon centers have had the reputation of being difficult. In the presence of a catalytic amount of m-trifluoromethylstyrene, an efficient cross-coupling reaction takes place between polyfunctional primary alkyl iodides and diorganozinc compounds [Eq. (a)] to give a general catalytic cross-coupling between sp³ carbon centers. Piv=pivaloyl; Pent = pentyl; acac = acetalacetonate; NMP = N-methylpyrrolidone.