Rhodium(III)-Catalyzed Alkenyl C-H Bond Functionalization: Convergent Synthesis of Furans and Pyrroles

被引：146

作者：

Lian, Yajing ^{[1
]}

Huber, Tatjana ^{[1
]}

Hesp, Kevin D. ^{[1
]}

Bergman, Robert G. ^{[2
,3
]}

Ellman, Jonathan A. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[3] Univ Calif Berkeley, Lawrence Berkeley Natl Lab, Berkeley, CA 94720 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 02期

基金：

加拿大自然科学与工程研究理事会;

关键词：

annulation; C-H activation; heterocycles; rhodium; synthetic methods; SUBSTITUTED FURANS; INTERNAL ALKYNES; POLYSUBSTITUTED FURANS; CATALYZED ANNULATION; ACTIVATION; CLEAVAGE; ALDEHYDES; ARYL; BENZAMIDES; DERIVATIVES;

D O I：

10.1002/anie.201207995

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ring in the new: A new annulation for the efficient synthesis of substituted furans and pyrroles is reported. The RhIII-catalyzed reaction of O-methyl α,β-unsaturated oximes with aldehydes and N-tosyl imines affords secondary alcohol and amine intermediates, respectively. Cyclization and aromatization occurs under the reaction conditions to provide access to biologically relevant furans and pyrroles in good yields. Cp*=C5Me5, DCE=1,2-dichloroethane, THF=tetrahydrofuran. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：629 / 633

页数：5

共 80 条

[1] Ruthenium-Catalyzed Hydroarylation of Methylenecyclopropanes through C-H Bond Cleavage: Scope and Mechanism [J].