Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates: development and optimization of a mild and stereospecific coupling process

被引：12

作者：

Denmark, Scott E. ^{[1
]}

Regens, Christopher S. ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 17期

基金：

美国国家卫生研究院;

关键词：

SUZUKI-MIYAURA; ARYL MESYLATES; ORGANOSILICON COMPOUNDS; PALLADIUM CATALYSTS; ARYLBORONIC ACIDS; GENERAL-METHOD; BORONIC ACIDS; TOSYLATES; VINYL; REAGENTS;

D O I：

10.1016/j.tetlet.2010.11.133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of an effective protocol for the palladium-catalyzed cross-coupling of (E)-alkenylsilanols with aryl triflates is described. A critical component in the optimization of this method was balancing the stability and reactivity of the triflates in the presence of a nucleophilic promoter. This report highlights the use of a slightly soluble Bronsted base promoter that allows for a low, steady-state concentration of alkenyl(dimethyl)silanolate in solution, thus facilitating cross-coupling in preference to S-O bond cleavage of the triflate. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2165 / 2168

页数：4

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