%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