Activated aryl chlorides: Useful partners for the coupling with 2-substituted thiazoles in the palladium-catalysed C-H activation/functionalisation reaction

被引：76

作者：

Gottumukkala, Aditya L. ^{[1
]}

Doucet, Henri ^{[1
]}

机构：

[1] Univ Rennes Catalyse & Organomet, Inst Sci Chim Rennes, CNRS, UMR 6226, F-35042 Rennes, France

来源：

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY | 2007年 / 23期

关键词：

aryl chlorides; catalysis; C-H activation; palladium; thiazoles;

D O I：

10.1002/ejic.200700420

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Aryl chlorides are noticeably uncommon partners in coupling reactions with heteroaromatics through C-H activation. We report herein that as little as 1 mol-% of the air-stable PdCl(dppb)(C3H5) complex catalyses the direct coupling of electron-deficient aryl chlorides with 2-substituted thiazole derivatives. A range of functionalities on the aryl chloride such as acetyl, formyl, ester, nitro, nitrile or trifluoromethyl is tolerated. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

引用

页码：3629 / 3632

页数：4

共 30 条

[1] Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (14) :3123-3125

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3]

AOYAGI Y, 1992, HETEROCYCLES, V33, P257

[4] Palladium-catalyzed direct arylation of furans via C-H functionalization at low catalyst loadings [J].

Battace, Ahmed ;

Lemhadri, Mhamed ;

Zair, Touriya ;

Doucet, Henri ;

Santelli, Maurice .

ORGANOMETALLICS, 2007, 26 (03) :472-474

[5] Synthesis of 6-allyl and 6-heteroarylindoles by palladium catalyzed Stille cross-coupling reaction [J].

Benhida, R ;

Lecubin, F ;

Fourrey, JL ;

Castellanos, LR ;

Quintero, L .

TETRAHEDRON LETTERS, 1999, 40 (31) :5701-5703

[6] Structural and kinetic effects of chloride ions in the palladium-catalyzed allylic substitutions [J].

Cantat, T ;

Génin, E ;

Giroud, C ;

Meyer, G ;

Jutand, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) :365-376

[7] Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides [J].

Chiong, Hendrich A. ;

Daugulis, Olafs .

ORGANIC LETTERS, 2007, 9 (08) :1449-1451

[8] Synthesis, incorporation into triplex-forming oligonucleotide, and binding properties of a novel 2′-deoxy-C-nucleoside featuring a 6-(thiazolyl-5)benzimidazole nucleobase [J].

Guianvarc'h, D ;

Fourrey, JL ;

Maurisse, R ;

Sun, JS ;

Benhida, R .

ORGANIC LETTERS, 2002, 4 (24) :4209-4212

[9]

Hara O, 2006, HETEROCYCLES, V68, P1

[10] Synthesis of 2-aryl-oxazolo[4,5-c]quinoline-4(5H)-ones and 2-aryl-thiazolo[4,5-c]quinoline-4(5H)-ones [J].

Hodgetts, KJ ;

Kershaw, MT .

ORGANIC LETTERS, 2003, 5 (16) :2911-2914

← 1 2 3 →