On the potential intermediacy of PhIBr2 as a brominating agent

PhIBr2, 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)-CF3)(2)) with TMSBr to form PhIBr(2)in situ and demonstrated its efficacy in aryl brominations. This report investigates this synthesis by replicating bromination reactions claiming to use in situ PhIBr2 as described. The spectroscopical and computational results indicate formation of PhI and Br-2 where Br-2 is responsible for bromination and no supporting evidence for invoking PhIBr2 as an intermediate is found.