Studies of microwave-enhanced Suzuki-Miyaura vinylation of electron-rich sterically hindered substrates utilizing potassium vinyltrifluoroborate

被引：11

作者：

Brooker, Matthew D. ^{[2
]}

Cooper, Stefan M., Jr. ^{[1
]}

Hodges, Dena R. ^{[1
]}

Carter, Rhiannon R. ^{[1
]}

Wyatt, Justin K. ^{[1
]}

机构：

[1] Coll Charleston, Dept Chem & Biochem, Charleston, SC 29424 USA

[2] Trident Tech Coll, Dept Chem, Charleston, SC 29455 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 51期

关键词：

Suzuki-Miyaura; Potassium vinyltrifluoroborate; Styrenes; Palladium catalysis; Hindered aryl bromides; CROSS-COUPLING REACTIONS; ARYL BROMIDES; CATALYST; CHLORIDES; HALIDES; ACIDS; SCOPE;

D O I：

10.1016/j.tetlet.2010.10.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Suzuki-Miyaura cross-coupling of sterically hindered and electron-rich ortho,ortho'-substituted aryl halides with potassium vinyltrifluoroborate utilizing microwave irradiation has been conducted while adjusting solvent ratio, irradiation time, and catalyst loading to find optimal conditions. Coupling of benzyl 3,5-bis(benzyloxy)-4-bromobenzoate leads to a mixture of the desired styrene derivative and the reduced product. 4-Bromo-1,3,5-trimethoxybenzene, methyl 4-bromo-3,5-dimethoxybenzoate, and mesitylene bromide were also coupled to test the breadth and scope of this methodology. Of these substrates tested only 4-bromo-1,3,5-trimethoxybenzene was not vinylated successfully, which is believed to be due to the electron-rich nature of this system. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6748 / 6752

页数：5

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