Dichlorobis(triphenylphosphine)nickel-catalyzed cross-coupling of aryl chlorides with intramolecularly stabilized group 13 metal alkylating reagents

The intramolecularly stabilized alkyl and aryl aluminum complexes 1, 4 and 11, as well as the indium compounds 6, 9 and 10 cross-couple with a variety of chloroarenes at 80°C in the presence of NiCl2(PPh3)2 to give selectively the respective alkylated arenes in high yields. Addition of organic or inorganic bases lowers the reaction temperature to 50°C.