Tetrahedron

Cp∗ Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines

K Fujita, Y Enoki, R Yamaguchi

Index: Fujita, Ken-ichi; Enoki, Youichiro; Yamaguchi, Ryohei Tetrahedron, 2008 , vol. 64, # 8 p. 1943 - 1954

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Citation Number: 205

Abstract

A versatile and highly atom economical catalytic system consisting of [Cp∗ IrCl2] 2/NaHCO3 (Cp∗= pentamethylcyclopentadienyl) for the N-alkylation of amines with primary and secondary alcohols as alkylating reagents has been developed. For example, the reaction of equimolar amounts of aniline and benzyl alcohol in the presence of [Cp∗ IrCl2] 2 (1.0 mol% Ir) and NaHCO3 (1.0 mol%) in toluene at 110° C gives N-benzylaniline in 94% yield. The ...