Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic C-S Coupling

被引：193

作者：

Bryan, Christopher S. ^{[1
]}

Braunger, Julia A. ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 1A1, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 38期

基金：

加拿大自然科学与工程研究理事会;

关键词：

cross-coupling; palladium; sulfur heterocycles; synthetic methods; tandem catalysis; ARYL HALIDES; BOND FORMATION; ONE-POT; PD; THIOLS; LIGAND; CARBON; ARYLATION; SULFIDES; DERIVATIVES;

D O I：

10.1002/anie.200902843

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The simultaneous construction of a C-S and a C-C bond under catalytic conditions forms the basis of an efficient route to diversely functionalized benzothiophenes from gem-dihalovinyl thiophenols. The C-C bond can be formed in this tandem catalytic process with an organoboron reagent as shown in the scheme (R1=H, Me, F, Cl, Br,-OCH2O-; R2=H, Me; R 3=aryl, heteroaryl, alkenyl, alkyl), or by Heck or Sonogashira coupling with an alkene or alkyne. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7064 / 7068

页数：5