FLP reactivity of [Ph 3 C] + and (o-tolyl) 3 P and the capture of a Staudinger reaction intermediate.

The frustrated Lewis pair (FLP) derived from the trityl cation and (o-tolyl)3 P effects the activation of 1,4-cyclohexadiene and 1-bromo-4-ethynylbenzene and heterolytically cleaves the S-S bond of diphenyl disulfide. The FLP also captures pentafluorophenyl azide as the Staudinger reaction intermediate, a species that reacts with Ph3 SiH to give the silyl analog.