Revisiting 1-chloro-1,2-benziodoxol-3-one: efficient ortho-chlorination of aryls under aqueous conditionsElectronic supplementary information (ESI) available: Copies of NMR spectra are available. See DOI: 10.1039/c8nj00530c

The application of 1-chloro-1,2-benziodoxol-3-one as a powerful chlorinating agent as well as oxidant for aniline derivatives is explored. The amide directing group assisted radical mediated ortho -selective chlorination proceeds in the absence of a radical initiator. Various electronically differen...

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Main Authors: Vinayak, Botla, Ravindrakumar, Pardhi Vishal, Ramana, Daggupati V, Chandrasekharam, Malapaka
Format: Article
Language:English
Online Access:Get full text
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Summary:The application of 1-chloro-1,2-benziodoxol-3-one as a powerful chlorinating agent as well as oxidant for aniline derivatives is explored. The amide directing group assisted radical mediated ortho -selective chlorination proceeds in the absence of a radical initiator. Various electronically differentiated anilides and sulfonamides are tolerated under aqueous conditions. The ortho -selective amide directing group assisted chlorination of aryls with the easily accessible 1-chloro-1,2-benziodoxol-3-one as oxidant as well as chlorinating reagent is reported in the absence of a radical initiator. The open air, aqueous conditions and recyclable reagent demonstrate the green principles involved in the reaction.
ISSN:1144-0546
1369-9261
DOI:10.1039/c8nj00530c