Multialkylation of Aqueous Ammonia with Alcohols Catalyzed by Water-Soluble Cp*Ir-Ammine Complexes

被引：267

作者：

Kawahara, Ryoko ^{[1
]}

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

Yamaguchi, Ryohei ^{[1
]}

机构：

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

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 43期

关键词：

TRANSITION-METAL; N-ALKYLATION; ENANTIOSELECTIVE HYDROGENATION; PRIMARY AMINES; ARYL HALIDES; REDUCTIVE AMINATION; SELECTIVE SYNTHESIS; HYDRIDE COMPLEXES; ALLYLIC AMINATION; TERTIARY-AMINES;

D O I：

10.1021/ja107274w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel water-soluble Cp*Ir-ammine complexes have been synthesized, and a new and highly atom-economical system for the synthesis of organic amines using aqueous ammonia as a nitrogen source has been developed. With a water-soluble and air-stable Cp*Ir-ammine catalyst, [Cp*Ir(NH3)(3)][1](2), a variety of tertiary and secondary amines were synthesized by the multialkylation of aqueous ammonia with theoretical equivalents of primary and secondary alcohols. The catalyst could be recycled by a facile procedure maintaining high activity. A one-flask synthesis of quinolizidine starting with 1,5,9-nonanetriol was also demonstrated. This new catalytic system would provide a practical and environmentally benign methodology for the synthesis of various organic amines.

引用

页码：15108 / 15111

页数：4

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