Xiao Yang , Rui Sun , Chunchun Zhang , Yan Zhang , Zhishan Su , Yicen Ge , Hua Chen , Haiyan Fu , Ruixiang Li
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引用次数: 2
Abstract
A direct C−H phosphonylation of pyridine by N‐benzylating activation is reported, which afforded 4‐pyridylphosphine oxides with high regioselectivity, without the employment of metal catalyst or expensive activator. By increasing the electrophilicity of pyridinium with electron‐withdrawing substituents on the N‐benzyl group, the phosphonylation process could be realized at room temperature. Control experiments and NMR investigation confirmed the interaction between DBU and diphenylphosphine oxide which generated the true phosphorus nucleophile. Moreover, DFT calculations offered enough insight into an intermolecular cooperative dehydrogenation‐debenzylation mechanism, which helped to elucidate the origin of C4‐regioselectivity in this metal‐free Chichibabin‐type phosphonylation.
期刊介绍：
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