Direct reversible decarboxylation from stable organic acids in dimethylformamide solution

We report that chemically stable C(sp3) carboxylates, such as arylacetic acids and malonate half-esters, undergo uncatalyzed reversible decarboxylation in dimethylformamide solution. Decarboxylation-carboxylation occurs with substrates resistant to protodecarboxylation by Brønsted acids under otherwise identical conditions. Isotopically labeled carboxylic acids can be prepared in high chemical and isotopic yield by simply supplying an atmosphere of 13CO2 to carboxylate salts in polar aprotic solvents. An understanding of carboxylate reactivity in solution enables conditions for the trapping of aldehydes, ketones, and α,β-unsaturated esters.

Source: ScienceNOW - July 29, 2020 Category: Science Authors: Kong, D., Moon, P. J., Lui, E. K. J., Bsharat, O., Lundgren, R. J. Tags: Chemistry reports Source Type: news