Phosphine-phosphonium ylides as ligands in palladium-catalysed C2-H arylation of benzoxazoles

被引：10

作者：

Yao, Zhenyu ^{[1
]}

Lin, Xing ^{[1
]}

Chauvin, Remi ^{[1
,2
,3
]}

Wang, Lianhui ^{[1
]}

Gras, Emmanuel ^{[2
,3
]}

Cui, Xiuling ^{[1
]}

机构：

[1] Huaqiao Univ, Sch Biomed Sci, Key Lab Xiamen Marine & Gene Drugs,Engn Res Ctr M, Minist Educ,Key Lab Fujian Mol Med,Key Lab Precis, Xiamen 361021, Peoples R China

[2] CNRS, Lab Coordinat Chem LCC, F-31077 Toulouse 4, France

[3] Univ Toulouse, UPS, INP, F-31077 Toulouse 4, France

来源：

CHINESE CHEMICAL LETTERS | 2020年 / 31卷 / 12期

基金：

中国国家自然科学基金;

关键词：

Electron-rich; Ligands; Phosphine-phosphonium-ylides; Benzixazole; C-H activation; OXIDATIVE ADDITION; ARYL HALIDES; COMPLEXES; HETEROCYCLES; ACTIVATION; CHEMISTRY; DIAMINOCARBENE; DERIVATIVES; REACTIVITY; TRIFLATE;

D O I：

10.1016/j.cclet.2020.04.008

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

As balanced electron-rich P,C-chelating ligands, phosphine-phosphonium-ylides are considered for their ability to in situ promote palladium-catalysed direct C(sp(2))-H arylation. Using methyl phosphonium salts of 2,2'-bis(diphenylphosphino)-1,1'-binaphtyl ("methyl-BINAPIUM") as ylide precursors under optimized reaction conditions, arylation of benzoxazole was found to proceed in moderate to high yield to give functional 2-aryl benzoxazoles. A strong anion effect of the non-salt free ylide was evidenced (TfO > I > PF6 approximate to salt-free). This first example of phosphonium ylides as ligands in catalytic C-H activation extends the prospect of their general implementation in homogeneous transition metal catalysis. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：3250 / 3254

页数：5

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