Tribromoisocyanuric Acid (TBCA)
Recent Literature
The reaction of tribromoisocyanuric acid with alkenes in the presence of
nucleophilic solvents (various alcohols, acetic acid, and H2O in
acetone) led to the corresponding β-bromoethers, β-bromoacetates and
bromohydrins in high regioselectivity and good yields.
L. S. de Almeida, P. M. Esteves, M. C. S. de Mattos, Synlett,
2006, 1515-1518.
The use of trihaloisocyanuric acid/triphenylphosphine enables a regioselective
conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides
under mild and neutral conditions in acetonitrile. The reactions proceed
smoothly in high yield at room temperature and at reflux, respectively, over a
short time.
V. S. C. de Andrade, M. C. S. de Mattos,
Synthesis, 2016, 48, 1381-1388.
Moderately deactivated arenes are efficiently brominated with 0.34 eq.
tribromoisocyanuric acid in trifluoroacetic acid at room
temperature. The use of trifluoroacetic acid avoids the polybromination of
the substrate, as can be observed in the same reaction performed in 98% H2SO4.
L. S. de Almeida, M. C. S. de Mattos, P. M. Esteves, Synlett, 2013, 24,
603-606.
The use of tribromoisocyanuric acid enables a simple and efficient one-pot
protocol for the synthesis of 2-aminothiazoles from readily available β-keto
esters via α-monohalogenation in aqueous medium and a subsequent reaction with
thiourea and DABCO. Extension of the reaction to thioacetamide and o-phenylenediamine
led to 2-methylthiazole and quinoxalines, respectively.
V. S. C. de Andrade, M. C. S. de Mattos, Synthesis, 2018, 50,
4867-4874.
