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

• 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

Identity

International Standard Serial Number (ISSN)

• 1523-7060

Digital Object Identifier (DOI)

• 10.1021/ol3034675

PubMed ID

• 23350852

Additional Document Info

start page

• 792

end page

• 795

volume

• 15

issue

• 4