98 / 2023-09-29 08:49:23

A Novel Phosphorylmethylation Reagent Based on Dibenzothiophene Skeleton

phosphorylmethylation,dibenzothiophene,indole,-CH2PO(OEt)2

New Technologies in Phosphorus Chemistry > 1) New reagents and methods in organophosphorus Chemistry

A novel electrophilic phosphorylmethylation reagent, namely, S-(diethyl methylphosphate)-dibenzothiophene salt I, was efficiently synthesized using readily available starting materials. The reagent can be synthesized on a gram scale and preserved stably. We explored its reactivity for the alkylation of indole derivatives, and interestingly found, the reagent exhibited selectivity at positions 2- and 3- which were crucial for the formation of C(sp²) - CH₂PO(OEt)₂ bonds.

Organic compounds with C-P (O) bonds have numerous applications in medicine, agricultural chemistry, and material chemistry. Alkyl phosphate esters and their derivatives play a critical role in the research and development of anticancer drugs, biological enzyme inhibitors, and other pharmaceuticals. However, practical ways for preparing it remain restricted. In our work, a novel reagent that can directly introduce -CH₂PO(OEt)₂ motif into organic molecules using dibenzothiophene framework. Based on its unique reactivity, selective alkylation of indole derivatives have been achieved with good yields. The reagent compound has the benefits of straightforward synthesis, convenience, efficiency, and easy access to raw materials. Its participation in the selective akylation of indoles with phosphorylmethyl group has the advantages of mild reaction conditions and good functional group tolerance.