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

共 91 条

[1] An improved cu-based catalyst system for the reactions of alcohols with aryl halides [J].

Altman, Ryan A. ;

Shafir, Alexandr ;

Choi, Alice ;

Lichtor, Phillip A. ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :284-286

[2] Resting State and Elementary Steps of the Coupling of Aryl Halides with Thiols Catalyzed by Alkylbisphosphine Complexes of Palladium [J].

Alvaro, Elsa ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7858-7868

[3] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[4] Palladium catalyzed alkenyl amination:: from enamines to heterocyclic synthesis [J].

Barluenga, J ;

Valdés, C .

CHEMICAL COMMUNICATIONS, 2005, (39) :4891-4901

[5] Copper-catalyzed synthesis of vinyl sulfides [J].

Bates, CG ;

Saejueng, P ;

Doherty, MQ ;

Venkataraman, D .

ORGANIC LETTERS, 2004, 6 (26) :5005-5008

[6] A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].

Bates, CG ;

Gujadhur, RK ;

Venkataraman, D .

ORGANIC LETTERS, 2002, 4 (16) :2803-2806

[7] Unusual influence of the structures of transition metal complexes on catalytic C-S and C-Se bond formation under homogeneous and heterogeneous conditions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) :3431-3444

[8]

Bolshan Y., 2008, Angewandte Chemie, V120, P2139

[9] Enamide synthesis by copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts [J].

Bolshan, Yuri ;

Batey, Robert A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2109-2112

[10] 2-(2,2-DIBROMOETHENYL)-BENZENAMINE [J].

Bryan, Christopher ;

Aurregi, Valentina ;

Lautens, Mark .

ORGANIC SYNTHESES, 2009, 86 :36-+

← 1 2 3 4 5 6 7 8 9 10 →