On the potential intermediacy of PhIBr2 as a brominating agent

Abstract

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 PhIBr₂in 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 Br₂ where Br₂ is responsible for bromination and no supporting evidence for invoking PhIBr₂ as an intermediate is found.