A highly selective decarboxylative deuteration of carboxylic acids

In this paper, we report a mild and practical method for precise deuteration of aliphatic carboxylic acids by synergistic photoredox and HAT catalysis. The reaction delivers excellent D-incorporation (up to 99%) at predicted sites even in substrates bearing reactive C-H bonds or versatile functional groups. The use of a recirculation reactor with a peristaltic pump supports a scalable preparative ability (up to 50 mmol) under very mild reaction conditions. The practical and precise deuteration of readily available complex carboxylic acids makes this protocol promising for the preparation of deuterium-labelled compounds.

Automated summary

This paper presents a mild and practical method for precise deuterium incorporation in aliphatic carboxylic acids using synergistic photoredox and HAT catalysis. The reaction shows excellent D-incorporation even in substrates with reactive C-H bonds or versatile functional groups, and can be scaled up to 50 mmol under very mild conditions. Precision deuteration of readily available complex carboxylic acids makes this protocol promising for the preparation of deuterium-labeled compounds.