An ionic liquid mediated Friedel-Crafts addition of arenes to isothiocyanates

被引：18

作者：

Naik, PU ^{[1
]}

Nara, SJ ^{[1
]}

Harjani, JR ^{[1
]}

Salunkhe, MM ^{[1
]}

机构：

[1] Inst Sci, Dept Chem, Bombay 400032, Maharashtra, India

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2003年 / 81卷 / 10期

关键词：

arenes; isothiocyanates; Friedel-Crafts; ionic liquids; thioamides;

D O I：

10.1139/V03-152

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new protocol is developed for the synthesis of N-substituted thioamides, employing arenes and isothiocyanates in 1-butyl-3-methylimidazolium chloroaluminate ionic liquid, [bmim]Cl.2AlCl(3), as a homogenous Lewis acid catalyst and solvent. The effect of Lewis acidity and the stoichiometry of the ionic liquid on the extent of product formation is studied. Studies reveal that a progressive increase in yields was observed with increasing Lewis acidity, and two equivalents of [bmim]Cl.2AlCl(3) was the optimal amount for the reaction. A distinct para selectivity for the incoming thioamido group on activated arenes was observed under ambient conditions.

引用

页码：1057 / 1060

页数：4

共 26 条

[1] A FAST-ATOM-BOMBARDMENT MASS-SPECTROMETRIC STUDY OF ROOM-TEMPERATURE 1-ETHYL-3-METHYLIMIDAZOLIUM CHLOROALUMINATE(III) IONIC LIQUIDS - EVIDENCE FOR THE EXISTENCE OF THE DECACHLOROTRIALUMINATE(III) ANION [J].