Palladium(0)-catalysed cross-coupling of 2-trimethylsilylpyridine with aryl halides

被引：19

作者：

Blakemore, David C. ^{[1
]}

Marples, Louise A. ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 32期

关键词：

2-Trimethylsilylpyrdine; Hiyama; Copper(I); Fluoride; ROOM-TEMPERATURE; BORONIC ACIDS; PALLADIUM; SILYLATION; CATALYST; ESTERS; MILD;

D O I：

10.1016/j.tetlet.2011.06.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for the Hiyama coupling reaction between aryl halides and 2-trimethylsilylpyridine has been developed. These conditions have been successfully applied to the synthesis of bis-heteroaryl systems, a key disconnection for the pharmaceutical industry in the synthesis of drug-like molecules. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4192 / 4195

页数：4

共 40 条

[1] Palladium-Catalyzed Cross-Coupling Reactions of 2-Pyridylborates with Air-Stable HASPO Preligands [J].

Ackermann, Lutz ;

Potukuchi, Harish K. .

SYNLETT, 2009, (17) :2852-2856

[2] SYNTHESIS OF ARYLSILANE AND HETEROARYLSILANE BY CLEAVAGE OF HEXAMETHYLDILANE [J].

BABIN, P ;

BENNETAU, B ;

THEURIG, M ;

DUNOGUES, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 446 (1-2) :135-138

[3] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].

Billingsley, Kelvin ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366

[4] A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles [J].

Billingsley, Kelvin L. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4695-4698

[5] Synthesis of novel halopyridinylboronic acids and esters. Part 4: Halopyridin-2-yl-boronic acids and esters are stable, crystalline partners for classical Suzuki cross-coupling [J].

Bouillon, A ;

Lancelot, JC ;

Santos, JSD ;

Collot, V ;

Bovy, PR ;

Rault, S .

TETRAHEDRON, 2003, 59 (50) :10043-10049

[6] Pd-PEPPSI-IPent: Low-Temperature Negishi Cross-Coupling for the Preparation of Highly Functionalized, Tetra-ortho-Substituted Biaryls [J].

Calimsiz, Selcuk ;

Sayah, Mahmoud ;

Mallik, Debasis ;

Organ, Michael G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (11) :2014-2017

[7] Applications of and alternatives to π-electron-deficient azine organometallics in metal catalyzed cross-coupling reactions [J].

Campeau, Louis-Charles ;

Fagnou, Keith .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1058-1068

[8] Negishi coupling of 2-pyridylzinc bromide-paradigm shift in cross-coupling chemistry? [J].

Coleridge, Brian M. ;

Bello, Charles S. ;

Ellenberger, David H. ;

Leitner, Andreas .

TETRAHEDRON LETTERS, 2010, 51 (02) :357-359

[9] Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates [J].

Deng, James Z. ;

Paone, Daniel V. ;

Ginnetti, Anthony T. ;

Kurihara, Hideki ;

Dreher, Spencer D. ;

Weissman, Steven A. ;

Stauffer, Shaun R. ;

Burgey, Christopher S. .

ORGANIC LETTERS, 2009, 11 (02) :345-347

[10] SYNTHESIS OF THE HELICOPODANDS - NOVEL SHAPES FOR CHIRAL CLEFTS [J].

DESHAYES, K ;

BROENE, RD ;

CHAO, I ;

KNOBLER, CB ;

DIEDERICH, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6787-6795

← 1 2 3 4 →