Catalyzes the coupling of Grignard reagents with allylic alcohols with displacement of the hydroxyl group: J. Chem. Soc., Chem. Commun., 1604 (1968). This alkene synthesis has been extended to enol ethers and methyl aryl ethers: J. Am. Chem. 101, 2246 (1979). The coupling of dithioacetals with Grignard reagents is also useful: Org. Synth. Coll., 9, 727 (1998),Catalyst for cross-coupling of organometallic reagents with aryl bromides: Tetrahedron Lett., 1389 (1977), and aryl tert-butyl sulfones: J. Chem. Soc., Perkin 1, 7 (1995), to give unsymmetrical biaryls. Symmetrical coupling of aryl halides can be effected in high yield with a Ni(0) catalyst generated in situ with Zn and triphenylphosphine in DMF, as a mild alternative to the Ullmann reaction: Tetrahedron Lett., 4089 (1977). For the analogous homocoupling of aryl mesylates, see: J. Org. Chem., 60, 176 (1995). The method has been extended to the formation aryl cyanides, providing an alternative to the classical CuCN route, and of diaryl sulfides: J. Org. Chem., 60, 6895 (1995). In the presence of Zn and pyridine, catalyzes the conjugate addition of alkyl bromides to ɑ?-unsaturated ketones, nitriles and esters: Russ. J. Gen. Chem., 65, 444 (1995).
