On the potential intermediacy of PhIBr<sub>2</sub> as a brominating agent.
null TaniaAndrew MolinoLachlan Sharp-BucknallDavid J D WilsonJason L DuttonPublished in: Organic & biomolecular chemistry (2022)
PhIBr<sub>2</sub>, first purported to exist over 100 years ago, has been subject of few reports due to its low stability. However, a recent publication proposes a reaction of PIFA (PhI(OC(O)-CF<sub>3</sub>)<sub>2</sub>) with TMSBr to form PhIBr<sub>2</sub><i>in situ</i> and demonstrated its efficacy in aryl brominations. This report investigates this synthesis by replicating bromination reactions claiming to use <i>in situ</i> PhIBr<sub>2</sub> as described. The spectroscopical and computational results indicate formation of PhI and Br<sub>2</sub> where Br<sub>2</sub> is responsible for bromination and no supporting evidence for invoking PhIBr<sub>2</sub> as an intermediate is found.