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

被引：276

作者：

Fujita, Ken-ichi ^{[1
,2
]}

Enoki, Youichiro ^{[1
]}

Yamaguchi, Ryohei ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Human & Environm Studies, Kyoto 6068501, Japan

[2] Kyoto Univ, Grad Sch Global Environm Studies, Kyoto 6068501, Japan

来源：

TETRAHEDRON | 2008年 / 64卷 / 08期

关键词：

iridium catalyst; hydrogen transfer; N-alkylation; amine; alcohol;

D O I：

10.1016/j.tet.2007.11.083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 degrees C gives N-benzylaniline in 94% yield. The present catalytic system is applicable to the N-alkylation of both primary and secondary amines, and only harmless water is produced as co-product. A wide variety of secondary and tertiary amines can be synthesized with high atom economy under mild and less-toxic conditions. One-pot sequential N-alkylation leading to tertiary amines bearing three different substituents is also described. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1943 / 1954

页数：12

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