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

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,...

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Bibliographic Details
Main Authors: Xin-Yue Niu, Chao-Yang Li, Cong-Cong Zhang, Zhan-Wei Bu, Yan Xie, Wen-Jing Zhang, Qi-Lin Wang
Format: Article
Language:English
Published: KeAi Communications Co. Ltd. 2025-05-01
Series:Green Synthesis and Catalysis
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Online Access:http://www.sciencedirect.com/science/article/pii/S2666554923001084
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Summary: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.
ISSN:2666-5549