A novel electrophilic phosphorylmethylating reagent, S-([diethoxyphosphoryl]methyl) dibenzothiophenium salt, has been successfully synthesized with readily available starting materials. This reagent is air- and moisture-tolerant and bench-stable. Interestingly, the reagent exhibited excellent selectivity for the formation of indole C (sp2) - CH2PO(OEt)2 bonds at position C2 with photo-catalyst and position C3 with Cu-catalyst. Moreover, the resulting compounds with CH2PO(OEt)2 could be easily converted into free phosphinic acid, providing a new pathway to prepare complex acid molecules.

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