Phosphole plays an important role in the modern organophosphorus chemistry. Due to its structure specialities, the exocyclic P-R σ bond shows significant interaction with the π* orbital of the dienic system and this overlap favors the [1,5]-sigmatropic shift of the substitutent (R) of P from phosphorus to carbon. This provides an efficient method to prepare various functionalized phospholes. This review is concerning the recent application of [1,5]-sigmatropic shift of phospholes in the organophosphorus and material chemistry.
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