Water-controlled skeletal editing or peripheral modification of ortho-chalcone-substituted organophosphines

Abstract

Skeletal editing of organophosphines is highly challenging owing to the high P-C bond dissociation energy. Herein, we report an efficient catalyst- and additive-free skeletal editing strategy to transform easily accessible ortho-chalcone based organophosphines into new and complex phosphine oxides, that are unattainable by conventional methods. Water is indispensable to this transformation and serves as the oxygen source to cleave P-C bonds. Interestingly, it is possible to achieve the peripheral modification of organophosphines into phosphonium salts in the absence of water. This water-controlled skeletal editing or peripheral modification strategy is embedded with the merits of high bond- and ring-forming efficiency and complete regio-, chemo- and stereoselectivity.