A SELECTIVE SYNTHESIS OF HYDROCARBONS BY CROSS-COUPLING USING ORGANICCOPPER SALT CATALYSTS

The cross-coupling reaction of the Grignard reagent with alkylating re actants (RBr, RI, and ROTs) was carried out in the presence of copper( II) acetate and organic copper(II) complex catalysts (0.01-0.05 molar amount) in tetrahydrofuran. The reaction readily gave higher hydrocarb ons (n-C-17 H-36, n-C23H48, n-C26H54, n-C27H56, n-C29H60, n-C30H62, an d n-C31H64), 1-phenyloctadecane, and 1-cyclohexyloctadecane as the des ired products in 90-99% isolated yields under mild conditions (-10 -60 degrees C, 2-5 h). In particular, copper(II.) acetate was found to be much more effective than conventional inorganic copper(II) salt catal ysts (Li2CuCl4, CuX(2)) from the viewpoints of availability, solubilit y, stability, and activity.