Regioselective Bromination of Fused Heterocyclic N-Oxides
Organic Letters2013Vol. 15(4), pp. 792–795
Citations Over TimeTop 10% of 2013 papers
Sarah E. Wengryniuk, Andreas Weickgenannt, Christopher A. Reiher, Neil A. Strotman, Ke Chen, Martin D. Eastgate, Phil S. Baran
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.
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