Abstract
Arylnickel and arylpalladium complexes which were easily prepared from aryl halide having internal double bond and the low valent metal complexes gave indole, oxindole, quinoline, isoquinoline and benzazepine derivatives. These reactions were highly regiospecific because the reaction occurred at the position of the halogen atom of the aromatic ring and the exo-position of the double bond. Since the insertion of carbon monoxide to this aryl or vinylmetal complex gave acylmetal complex, aryl and vinyl halide having functional group such as amine, alcohol and amide were treated with a catalytic amount of PdII and PPh3 under carbon monoxide to give benzolactam, benzolactone, cyclic imide and α-methylene lactam and lactone. By using this method, α-methylene-β-lactams and α-alkylidene-β-lactams were synthesized from 2-bromo-allylamine derivatives. Moreover, natural compounds, sendaverine, anthramycin skeletone and 3-aminonocardicinic acid were synthesized by this method.
