N-Alkylation of carbamates and amides with alcohols catalyzed by a Cp*Ir complex

被引：69

作者：

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

Komatsubara, Atsuo ^{[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 | 2009年 / 65卷 / 18期

关键词：

Iridium catalyst; N-Alkylation; Carbamate; Alcohol; DIRECT ALPHA-ALKYLATION; SECONDARY ALCOHOLS; TERTIARY-AMINES; BORROWING HYDROGEN; ORGANIC-SYNTHESIS; RUTHENIUM; EFFICIENT; AMINATION; ACTIVATION; ALDEHYDES;

D O I：

10.1016/j.tet.2009.03.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New atom-economical catalytic systems consisting of [Cp*IrCl2](2)/NaOAc (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of carbamates and amides using alcohols as alkylating agents under solvent-free conditions have been developed. For example, the reaction of n-butyl carbamate with benzyl alcohol in the presence of [Cp*IrCl2](2) (5.0 mol % Ir) and NaOAc (5.0 mol %) at 130 degrees C under the absence of solvent gives n-butyl N-benzylcarbamate in the yield of 94%. The present catalytic system is applicable to not only carbamates but also amides, and only harmless water is produced as co-product. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3624 / 3628

页数：5

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