Structure and reactivity of (η3-indolylmethyl) palladium complexes generated by the reaction of organopalladium complexes with o-alkenylphenyl isocyanide

The reaction of methylpalladium complexes with o-alkenylphenyl isocyanides results in the successive intramolecular insertion of the alkenyl and isocyano groups followed by the 1,3-migration of hydrogen to give (eta(3)-indolylmethyl)palladium complexes (4) in good yields. Treatment of 4 with diethylamine causes nucleophilic attack at the exo methylene carbon to give 2-methyl-3-(aminomethyl)indole, whereas the reactions with HCl produce 2,3-dimethylindole derivatives.