Zr-Catalyzed Coupling Reaction of Alkyl Halides, Tosylates, and Sulfates with (beta)-Phenethyl Grignard Reagents via Styrene-Zirconate Intermediates

(beta)-Phenethylmagnesium chlorides react with alkyl halides, tosylates, and sulfates in the presence of a catalytic amount of Cp2ZrCl2 to afford 2-arylalkanes via alkylation of styrene-zirconate intermediates at the benzylic position. Competitive reaction using mixtures of alkyl halides (alkyl-X; X = F, Cl, Br) showed that the reactivities of the halides increase in the order of alkyl-Cl < alkyl-F < alkyl-Br with the relative rates of 1:19:428.