Direct Trideuteromethylselenation with a Shelf-Stable Reagent Se-Methyl-d3 Selenosulfonate

Abstract

Direct incorporation of deuterauted functionalizties into molecules has emerged as an attractive approch in organic synthesis. Among them, the deuterauted selenomethyl is of great interest bue still less explored due to the lack of versatile synthons. Here, an electrophilic trideuteromethylselenating reagent, S-Methyl-d3 benzenesulfonoselenoate with >99% D-incorporation has been developed, which can be facilely prepared in one step and enable trideuteromethylselenation for a wide range of nucleophiles or electrophiles including boronic acids, boronic acids esters, terminal alkynes, -ketoesters, oxindoles and diazodium salts under mild reaction conditions. Moreover, difunctionalization of unactivated of alkenes by simultaneously construction of C-S and C-SeCD3 bonds are well-documented. The utility of odourless electrophilic SeCD3 reagent has been highlighted by late-stage modification of bioactive molecules with high efficiency.