Tandem Synthesis of Amides and Secondary Amines from Esters with Primary Amines under Solvent-Free Conditions

被引：25

作者：

Lee, Jeongbin ^{[1
,2
]}

Muthaiah, Senthilkumar ^{[2
]}

Hong, Soon Hyeok ^{[1
,2
]}

机构：

[1] Inst for Basic Sci Korea, Ctr Nanoparticle, Seoul 151742, South Korea

[2] Seoul Natl Univ, Dept Chem, Coll Nat Sci, Seoul 151747, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 11-12期

基金：

新加坡国家研究基金会;

关键词：

amides; amines; esters; hydrogen transfer; iridium; ASTERISK-IR COMPLEX; CATALYZED N-ALKYLATION; BORROWING HYDROGEN METHODOLOGY; REDUCTIVE AMINATION; INTERMOLECULAR HYDROAMINATION; TEMPLATED MACROLACTAMIZATION; EFFICIENT CATALYST; SPERMINE ALKALOIDS; CARBONYL-COMPOUNDS; ORGANIC-SYNTHESIS;

D O I：

10.1002/adsc.201400319

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An iridium(III)-catalyzed tandem synthesis of amides and amines from esters under solvent-free conditions is described. A commercially available iridium(III) complex, [Cp*IrCl2](2), with sodium acetate showed the best activity for the synthesis of amides and secondary amines. The amide was formed by ester-amide exchange which generates an alcohol in situ which is subsequently transformed to a secondary amine via hydrogen autotransfer. This synthetic protocol with high atom economy generates water as the sole by-product and can afford amides and amines from various esters in a one-pot reaction, expanding the synthetic versatility of ester transformations.

引用

页码：2653 / 2660

页数：8