Direct reversible decarboxylation from stable organic acids in dimethylformamide solution

Abstract

Simple swaps of CO 2 The loss of carbon dioxide (CO 2 ) from carboxylic acids is a common reaction in both biochemical and synthetic contexts, but it has generally involved catalysis or prolonged heating. Kong et al. now report that certain polar solvents, such as dimethylformamide, promote reversible CO 2 loss all by themselves from carboxylates bridged by one carbon to aromatic rings. With electron-withdrawing substituents on the ring, isotopically labeled CO 2 can be efficiently swapped in even at room temperature. Alternatively, reaction with aldehydes leads to alcohol formation. Science , this issue p. 557