NICKEL AND PALLADIUM-CATALYZED CROSS-COUPLINGS THAT FORM CARBON-HETEROATOM AND CARBON-ELEMENT BONDS

The transition-metal catalyzed addition of heteroatom nucleophiles to aryl and vinyl halides is reviewed. This chemistry typically involves a nickel-or palladium-based catalyst containing phosphine ligands. In recently developed palladium-catalyzed chemistry, aryl halides react w ith amines in the presence of base to form arylamines. In similar chem istry catalyzed by both nickel and palladium, aryl and vinyl halides r eact with alkali metal or tin thiolates or selenides to form aryl and vinyl sulfides, while the reaction of different phosphorus compounds, such as phosphides, phosphonates, and phosphonites, with aryl halides gives compounds with new aryl-p linkages. In addition to these typical ly nucleophilic heteroatoms, electrophilic heteroatoms such as boron, silicon, tin, and germanium have also been coupled to aryl electrophil es, The review closes with a brief summary of the general reaction pat hways of these C-X bond-forming processes.