General and highly efficient fluorinated-N-heterocyclic carbene-based catalysts for the palladium-catalyzed Suzuki-Miyaura reaction

被引：25

作者：

Liu, Taoping ^{[1
]}

Zhao, Xiaoming ^{[1
]}

Shen, Qilong ^{[1
]}

Lu, Long ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 32期

基金：

中国国家自然科学基金;

关键词：

Suzuki-Miyaura reaction; Fluoride; N-Heterocyclic carbene; Aryl halides; Heteroaryl halides; CROSS-COUPLING REACTIONS; ARYL HALIDES; HETEROARYLBORONIC ACIDS; BUCHWALD-HARTWIG; ALKYL BROMIDES; BORONIC ACIDS; LIGANDS; COMPLEXES; CHLORIDES; NHC;

D O I：

10.1016/j.tet.2012.05.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and highly efficient trifluoromethylated-N-heterocyclic carbene (NHC)-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction was reported. In the presence of the catalyst, reactions of non-activated aryl chlorides and triflates with aryl boronic acids occurred at room temperature with good to excellent yields (63-98%). In addition, catalysts generated from a combination of Pd(OAc)(2)/imidazolium salt 6a is not only effective for the coupling of heteroaryl boronic acid with aryl halides and heteroaryl halides, but also efficient for coupling of other heteroaryl halides and heteroaryl boronic acids. Finally, the catalyst is highly effective for Suzuki-Miyaura reaction of aryl bromides and chlorides with 0.01-0.1 mol % loading if the temperature was raised at refluxed THF/H2O. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6535 / 6547

页数：13

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