A practical and environmentally friendly protocol for synthesis of α-deuterated carboxylic acids

alpha-deuterated carboxylic acids have been synthesized from the corresponding malonic acids via hydrogen/deuterium exchange and decarboxylation in presence of D2O. The method is general, mild and efficient and does not require organic solvents or other additives. Yields range between 83% and 94% and purification was not necessary. Starting materials were easy accessible and the alpha-deuterated carboxylic acids may easily be transformed to other labeled compounds such as alcohols, aldehydes, esters, and amides. Characterization with NMR confirmed purity and isotopic purity.

Automated summary

Alpha-deuterated carboxylic acids were synthesized from malonic acids via hydrogen/deuterium exchange and decarboxylation in the presence of D2O. The method is general, mild, and efficient, and does not require organic solvents or other additives. Yields ranged from 83% to 94%, and purification was not necessary. The alpha-deuterated carboxylic acids can be easily transformed into other labeled compounds such as alcohols, aldehydes, esters, and amides. Characterization with NMR confirmed purity and isotopic purity.