Tetrahedron

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

J Barluenga, J Perez-Prieto, G Asensio

Index: Barluenga, Jose; Perez-Prieto, Julia; Asensio, Gregorio Tetrahedron, 1990 , vol. 46, # 7 p. 2453 - 2460

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Citation Number: 12

Abstract

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.