A ligand free copper(II) catalyst is as effective as a ligand assisted Pd(II) catalyst towards intramolecular C-S bond formation via C-H functionalization

被引：41

作者：

Banerjee, Arghya ^{[1
]}

Santra, Sourav Kumar ^{[1
]}

Rout, Saroj Kumar ^{[1
]}

Patel, Bhisma K. ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

TETRAHEDRON | 2013年 / 69卷 / 43期

关键词：

C-H functionalization; C-S bond formation; Cu-catalysis; Pd-catalysis; Ligand assistance; ONE-POT SYNTHESIS; 2-SUBSTITUTED BENZOTHIAZOLES; CONTROLLED REGIOSELECTIVITY; OXYGEN; HETEROCYCLES; ACTIVATION; AMIDATION; STRATEGY; WATER;

D O I：

10.1016/j.tet.2013.08.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(I) catalysts are usually ineffective on the other hand Pd(II) catalysts are quite effective in promoting intramolecular sp(2) C-H functionalization (C-S bond formation). Herein, we have developed a ligand assisted Pd(II) catalyzed C-S bond formation via C-H activation from arylthioureas leading to the formation of 2-aminobenzothiazoles for substrates bearing electron donating (EDG) groups in the aryl ring. However without the assistance of ligand this Pd(II) catalyzed reaction is quite unproductive particularly for thioureas possessing strongly electron donating groups in the aryl rings. Interestingly, the ligand free Cu(II) catalyzed oxidative cyclization of arylthioureas are equally effective both for arylthioureas possessing electron donating as well as electron withdrawing groups in the aryl rings. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

引用

页码：9096 / 9104

页数：9

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