Palladium catalyzed ortho-halogenation of 2-arylbenzothiazole and 2,3-diarylquinoxaline

被引：36
作者：
Santra, Sourav Kumar [1 ]
Banerjee, Arghya [1 ]
Khatun, Nilufa [1 ]
Samanta, Asim [1 ]
Patel, Bhisma K. [1 ]
机构：
[1] Indian Inst Technol Guwahati, Dept Chem, Assam 781039, India
来源：
RSC ADVANCES | 2015年 / 5卷 / 16期
关键词：
C-H BONDS; SELECTIVE ORTHO-BROMINATION; CROSS-COUPLING REACTIONS; IODINATION; ACTIVATION; COMPLEXES; FUNCTIONALIZATION; ARYLATION; DERIVATIVES; OLEFINATION;
D O I：
10.1039/c4ra15461d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A palladium catalysed ortho-halogenation strategy has been developed using benzothiazoles and quinoxalines as the directing substrates. This method provides mono-o-halogenated product at the other available ortho site of a mono-ortho substituted 2-arylbenzothiazole. However, orthounsubstituted 2-arylbenzothiazole afforded di-ortho halogenated product exclusively. The preformed (or installed) ortho-group is towards the sulphur side of the benzothiazole from energy minimised calculation. Thus the selective formation of di-ortho-halogenated products is due to favourable exposure of the second ortho site for subsequent halogenation. However the phenyl ring in 2,3-diarylquinoxalines can be selectively mono ortho halogenated. A plausible reaction mechanism has been proposed for this halogenation process.
引用
收藏
页码：11960 / 11965
页数：6
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