Tribromoisocyanuric Acid (TBCA)
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.