Direct synthesis of bipyrroles using phenyliodine bis(trifluoroacetate) with bromotrimethylsilane

The hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), mediates the unprecedented, oxidative coupling reaction of pyrroles to give a-linked bipyrroles selectively in the presence of bromotrimethylsilane. This straightforward synthesis could provide 2,3'-bipyrrole by the choice of a N-substituent of pyrrole. Mechanistic consideration of the present reaction is also described.