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Copper(I) halide mediated tandem 1,4-aryl migration-oxidative amidyl radical cyclisation of bromosulfonamides

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Clark, Andrew J., Fullaway, David R., Murphy, Nicholas P. and Parekh, Hemal (2010) Copper(I) halide mediated tandem 1,4-aryl migration-oxidative amidyl radical cyclisation of bromosulfonamides. Synlett (No.4). pp. 610-614. doi:10.1055/S-0029-1219151 ISSN 0936-5214.

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Official URL: http://dx.doi.org/10.1055/s-0029-1219151

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Abstract

Reaction of N-butyl-N-(2-bromo-2-methylpropionyl)-arylsulfonamides with CuBr/tripyridylamine leads to amidyl radicals via 1,4-aryl migration with concomitant loss of SO2, which can further undergo cyclisation to oxindoles or reduction to amides with the ratio dependent upon the temperature and solvent utilised.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH): Copper, Free radical reactions, Ring formation (Chemistry), Sulfonamides
Journal or Publication Title: Synlett
Publisher: Georg Thieme Verlag
ISSN: 0936-5214
Official Date: March 2010
Dates:
DateEvent
March 2010Published
Number: No.4
Number of Pages: 5
Page Range: pp. 610-614
DOI: 10.1055/S-0029-1219151
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access
Funder: Engineering and Physical Sciences Research Council (EPSRC)
Grant number: EP/F016573 (EPSRC)

Data sourced from Thomson Reuters' Web of Knowledge

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