Electrosynthesis of Phosphacycles via Dehydrogenative C–P Bond Formation Using DABCO as a Mediator
Yuji Kurimoto, Jun Yamashita, Koichi Mitsudo, Eisuke F. Sato, Seiji Suga
Abstract
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.
Topics & Concepts
ChemistryDABCOElectrosynthesisMediatorElectrochemistryCombinatorial chemistryHydrogen bondHydrogen atomMoleculeOctaneStereochemistryMedicinal chemistryOrganic chemistryGroup (periodic table)Physical chemistryElectrodeInternal medicineMedicineRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods