Dichloropalladium(II): An Effective Catalyst for Cross-Coupling of secondary and Primary Alkyl Grignard and Alkylzinc Reagents with Organic Halides

Article abstract of DOI:10.1021/ja00313a032

Several phosphine-palladium and -nickel complexes were examined for their catalytic activity in the reaction of sec-butylmagnesium chloride with bromobenzene, (E)-β-bromostyrene, 4-bromoanisole, and 2-bromotoluene.Dichloro<1,1'-bis(diphenylphosphino)ferrocene>palladium(II) was found to be by far the most active and selective catalyst to give the corresponding sec-butyl derivatives in high yields with no byproducts.The palladium-dppf complex was also found highly effective in catalyzing the reaction of n-butylmagnesium chloride and sec- and n- butylzinc chloride with organic bromides to give the corresponding cross-coupling products in high yields.The structure of PdCl2(dppf) has been determined by an X-ray diffraction study.It is proposed that the high efficiency of PdCl2(dppf) catalyst can be ascribed to its large P-Pd-P angle and small Cl-Pd-Cl angle.