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Regioselective bromination of fused heterocyclic N-oxides

Academic Article
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Overview

authors

  • Wengryniuk, S. E.
  • Weickgenannt, A.
  • Reiher, Chris
  • Strotman, N. A.
  • Chen, K.
  • Eastgate, M. D.
  • Baran, Phil

publication date

  • February 2013

journal

  • Organic Letters  Journal

abstract

  • A mild method for the regioselective C2-bromination of fused azine N-oxides is presented, employing tosic anhydride as the activator and tetra-n-butylammonium bromide as the nucleophilic bromide source. The C2-brominated compounds are produced in moderate to excellent yields and with excellent regioselectivity in most cases. The potential extension of this method to other halogens, effecting C2-chlorination with Ts(2)O/TBACl is also presented. Finally, this method could be incorporated into a viable one-pot oxidation/bromination process, using methyltrioxorhenium/urea hydropgen peroxide as the oxidant.

subject areas

  • Catalysis
  • Cyclic N-Oxides
  • Halogenation
  • Hydrocarbons, Brominated
  • Molecular Structure
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol3034675

PubMed ID

  • 23350852
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Additional Document Info

start page

  • 792

end page

  • 795

volume

  • 15

issue

  • 4

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