Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators

被引：255

作者：

Neely, Jamie M. ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 07期

关键词：

ONE-POT SYNTHESIS; SUBSTITUTED PYRIDINE-DERIVATIVES; GRAM-SCALE SYNTHESIS; DE-NOVO SYNTHESIS; ALPHA; BETA-UNSATURATED KETOXIMES; FUNCTIONALIZED PYRIDINES; REGIOSELECTIVE SYNTHESIS; AROMATIC CARBOXYLATES; DIRECTING GROUPS; BIARYL SYNTHESIS;

D O I：

10.1021/ja412444d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha/beta-Unsaturated carboxylic acids undergo Rh(III)-catalyzed decarboxylative coupling with alpha,beta-unsaturated O-pivaloyl oximes to provide substituted pyridines in good yield. The carboxylic acid, which is removed by decarboxylation, serves as a traceless activating group, giving 5-substituted pyridines with very high levels of regioselectivity. Mechanistic studies rule out a picolinic acid intermediate, and an isolable rhodium complex sheds further light on the reaction mechanism.

引用

页码：2735 / 2738

页数：4

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