Tetrahedron

Metallation of benzylic amines via amine-borane complexes

MR Ebden, NS Simpkins, DNA Fox

Index: Ebden, Mark R.; Simpkins, Nigel S.; Fox, David N.A. Tetrahedron, 1998 , vol. 54, # 42 p. 12923 - 12952

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Citation Number: 32

Abstract

Formation of borane complexes of N, N-dimethylbenzylamine, N, N-dimethyl (1-naphthyl) methylamine, N, N-dimethyl (2-naphthyl) methylamine, N-methyltetrahydroisoquinoline and N-methylisoindoline facilitates regioselective metallation of these systems using BuLi, giving intermediate benzylic anions which react with a range of electrophiles to give products in good yield.