Green synthesis of α-deuterated boronates using DMTT reagent
Zedong Zhang, Jian Wen, Minyan Wang, Chao‐Guo Yan, Zhuangzhi Shi
Abstract
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-sulfur-methylene 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 one-carbon growth under the practical mild conditions.
Topics & Concepts
ChemistryMethyleneReagentDeuteriumDeprotonationYlideCarbon atomBoronic acidSulfonateCombinatorial chemistryOrganic chemistryMedicinal chemistryRing (chemistry)IonQuantum mechanicsPhysicsSodiumChemical Reactions and IsotopesBoron Compounds in ChemistryAsymmetric Hydrogenation and Catalysis