Catalytic aminomercuration of olefins in a tandem aminomercuration-deoxymercuration; one-step synthesis of secondary n-arylallylamines from allylalcohols

Article abstract of DOI:10.1016/S0040-4020(01)82026-3

Allyl alcohols react with primary aromatic amines and stoichiometric amounts of mercury(II) tetrafluoroborate to give mixtures of mono- and diallyl anilines. However, the use of the tandem aminomercuration-deoxymercuration promoted by catalytic mercury(II) tetrafluoroborate allows to perform regiospecifically the monoallylation reaction with very high yields. A mechanism is proposed to account for the observed results.