Chemoselective Copper-Catalyzed Acylation of Benzothiazoles with Aryl Methyl Ketones

被引：30

作者：

Feng, Qiang ^{[1
]}

Song, Qiuling ^{[1
]}

机构：

[1] Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Chem Engn, Xiamen 361021, Fujian, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 11-12期

基金：

美国国家科学基金会;

关键词：

acylation; 2-acylbenzothiazoles; aryl methyl ketones; benzothiazoles; oxidation; AEROBIC OXIDATIVE SYNTHESIS; C-H ARYLATION; DECARBOXYLATIVE ARYLATION; ALPHA-KETOAMIDES; 2-ACYLBENZOTHIAZOLES; SYSTEM; AMINES; ACIDS; NIS;

D O I：

10.1002/adsc.201400240

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A copper(I) iodide-catalyzed, highly efficient acylation of benzothiazoles with aryl methyl ketones as carbonyl sources under a nitrogen atmosphere was developed. This is an unprecedented protocol and an extremely efficient method for the selective synthesis of 2-acylbenzothiazoles from commercially available, cheap starting materials with excellent chemoselectivity, good functional group tolerability and high turnover numbers (up to 14,200); also scaling up to 160 mmol without loss of the efficiency is possible. A variety of 2-acylbenzothiazoles was smoothly prepared in good to excellent yields from aryl methyl ketones and benzothiazoles by a one-pot domino protocol of combined sp(3) C-H oxidation, ring opening, and condensation.

引用

页码：2445 / 2452

页数：8

共 26 条

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