%0 Journal Article %A Wengryniuk, Sarah E. %A Weickgenannt, Andreas %A Reiher, Christopher %A Strotman, Neil A. %A Chen, Ke %A Eastgate, Martin D. %A Baran, Phil S. %D 2013 %T Regioselective Bromination of Fused Heterocyclic N‑Oxides %U https://acs.figshare.com/articles/journal_contribution/Regioselective_Bromination_of_Fused_Heterocyclic_i_N_i_Oxides/2442946 %R 10.1021/ol3034675.s001 %2 https://acs.figshare.com/ndownloader/files/4085605 %K nucleophilic bromide source %K tosic anhydride %K method %K Ts 2O %K Regioselective Bromination %X 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 Ts2O/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. %I ACS Publications