Green synthesis of & alpha;-deuterated boronates using DMTT reagent

An efficient method for the synthesis of deuterated homologation of boronate esters was developed. This discovery uses robust deuterated agent 5-(methyl-d3)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethane sulfonate (DMTT) as d2-methylene source. Mechanistically, base promoted deprotonation of DMTT to generate d2-sulfurmethylene ylide intermediate, which attack the boron atom of boronic ester and followed by 1,2-migration to afford the deuterated boronic homologues. The developed protocol provides a unique approach to achieve onecarbon growth under the practical mild conditions.

Automated summary

An efficient method for the synthesis of deuterated homologation of boronate esters was developed using DMTT as d2-methylene source. The reaction mechanism involves base promoted deprotonation of DMTT to generate d2-sulfurmethylene ylide intermediate, which attacks the boron atom of boronic ester followed by 1,2-migration to afford the deuterated boronic homologues. This provides a unique approach to achieve one-carbon growth under practical mild conditions.