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

Santra, Sourav Kumar ; Banerjee, Arghya ; Khatun, Nilufa ; Samanta, Asim ; Patel, Bhisma K. (2015) Palladium catalyzed ortho-halogenation of 2-arylbenzothiazole and 2,3-diarylquinoxaline RSC Advances, 5 (16). pp. 11960-11965. ISSN 2046-2069

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Official URL: http://pubs.rsc.org/en/content/articlelanding/2015...

Related URL: http://dx.doi.org/10.1039/C4RA15461D

Abstract

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, ortho-unsubstituted 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.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:113816
Deposited On:02 May 2018 04:47
Last Modified:02 May 2018 04:47

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