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 a photocatalyst and at position C3 with a copper catalyst. Moreover, the resulting compounds with CH₂PO(OEt)₂ could be easily converted into free phosphinic acid, providing a new pathway for preparing complex acid molecules.

中文翻译：

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使用磷酰甲基二苯并噻吩鎓试剂对吲哚进行选择性 C2 和 C3 磷酰甲基化


一种新型亲电磷酰甲基化试剂，S-([二乙氧基磷酰基]甲基)二苯并噻吩鎓盐，已用易于获得的起始原料成功合成。该试剂具有耐空气性和耐湿性，并且在工作台上稳定。有趣的是，该试剂在光催化剂作用下，在 C2 位形成吲哚 C(sp ² )–CH ₂ PO(OEt) ₂ 键时表现出优异的选择性并在位置C3用铜催化剂。此外，所得的CH ₂ PO(OEt) ₂ 化合物可以很容易地转化为游离次膦酸，为制备复杂酸分子提供了新的途径。