Direct Arylation of N-Heteroarenes with Aryldiazonium Salts by Photoredox Catalysis in Water

被引：146

作者：

Xue, Dong ^{[1
]}

Jia, Zhi-Hui ^{[1
]}

Zhao, Cong-Jun ^{[1
]}

Zhang, Yan-Yan ^{[1
]}

Wang, Chao ^{[1
]}

Xiao, Jianliang ^{[1
,2
]}

机构：

[1] Shaanxi Normal Univ, Minist Educ, Sch Chem & Chem Engn, Key Lab Appl Surface & Colloid Chem, Xian 710062, Peoples R China

[2] Univ Liverpool, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 10期

基金：

英国工程与自然科学研究理事会; 中国国家自然科学基金;

关键词：

aryldiazonium salts; cross-coupling; green chemistry; N-heteroarenes; photoredox catalysis; water; C-H ARYLATION; VISIBLE-LIGHT PHOTOREDOX; ARYL BOND FORMATION; XANTHINE DERIVATIVES; HIGHLY POTENT; HETEROCYCLES; FUNCTIONALIZATION; TRIFLUOROMETHYLATION; PHOTOCATALYSIS; DISCOVERY;

D O I：

10.1002/chem.201304120

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly effective visible light-promoted radical-type coupling of N-heteroarenes with aryldiazonium salts in water has been developed. The reaction proceeds at room temperature with [Ru(bpy)(3)]Cl(2)6H(2)O as a photosensitizer and a commercial household light bulb as a light source. Pyridine and a variety of substituted pyridines are effective substrates under these reaction conditions, and only monosubstituted products are formed with different regioselectivities. Using aqueous formic acid as solvent, an array of xanthenes, thiazole, pyrazine, and pyridazine are compatible with this new arylation approach. The broad substrate scope, mild reaction conditions, and use of water as reaction solvent make this procedure a practical and environmentally friendly method for the synthesis of compounds containing aryl-heteroaryl motifs.

引用

页码：2960 / 2965

页数：6

共 108 条

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