Reactions of Frustrated Lewis Pairs with Chloro-Diazirines: Cleavage of N=N Double Bonds

The reactions of FLPs with diazomethanes leads to the rapid loss of N-2. In contrast, in this work, we reported reactions of phosphine/borane FLPs with chlorodiazirines which led to the reduction of the N=N double bond, affording linked phosphinimide/amidoborate zwitterions of the general form R3PNC(Ar)NR ' BX(C6F5)(2). A detailed DFT mechanistic study showed that these reactions proceed via FLP addition to the N=N bond, followed by subsequent group transfer reactions to nitrogen and capture of the halide anion.

Automated summary

In this work, we reported the reactions of phosphine/borane FLPs with chlorodiazirines, which resulted in the reduction of the N=N double bond and formation of phosphinimide/amidoborate zwitterions. A mechanistic study using DFT showed that these reactions proceed through FLP addition and subsequent group transfer reactions to nitrogen, followed by the capture of a halide anion.