Heterodimerization of propylene and vinylarenes: Functional group compatibility in a highly efficient Ni-catalyzed carbon-carbon bond-forming reaction

Unlike heterodimerization reactions of ethylene and vinylarenes, no such sy nthetically useful reactions using propylene are known. We find mat propyle ne reacts with various vinylarenes in the presence of catalytic amounts of [(allyl)NiBr](2), triphenylphosphine and AgOTf giving excellent yields of t he dimerization products. The reaction proceeds at 1 atm of propylene at te mperatures between -15 and 10 degrees C. These conditions are compatible wi th a number of common organic functional groups such as halides, ethers, es ters, ketones and sulfonamides. As expected, a mixture of regioisomeric pro ducts (with propene-C-1 addition to the benzylic position as the major one) is obtained. The product distribution appears to be significantly differen t when a hemilabile ligand (2-diphenylphosphino-2'-alkoxy-1,1'-binaphthyl) is employed. (C) 2000 Elsevier Science Ltd. All rights reserved.