Electrosynthesis of Phosphacycles via Dehydrogenative C-P Bond Formation Using DABCO as a Mediator

The first electrochemical synthesis of diarylphosphole oxides (DPOs) was achieved under mild conditions. The practical protocol employs commercially available and inexpensive DABCO as a hydrogen atom transfer (HAT) mediator, leading to various DPOs in moderate to good yields. This procedure can also be applied to the synthesis of six-membered phosphacycles, such as phenophosphazine derivatives. Mechanistic studies suggested that the reaction proceeds via an electro-generated phosphinyl radical.

Automated summary

The first electrochemical synthesis of diarylphosphole oxides (DPOs) was achieved under mild conditions using commercially available and inexpensive DABCO as a hydrogen atom transfer mediator. The procedure resulted in moderate to good yields of various DPOs and can also be used for the synthesis of six-membered phosphacycles. Mechanistic studies suggested that the reaction proceeds via an electro-generated phosphinyl radical.