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Direct reversible decarboxylation from stable organic acids in dimethylformamide solution

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Science  31 Jul 2020:
Vol. 369, Issue 6503, pp. 557-561
DOI: 10.1126/science.abb4129

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Simple swaps of CO2

The loss of carbon dioxide (CO2) 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 CO2 loss all by themselves from carboxylates bridged by one carbon to aromatic rings. With electron-withdrawing substituents on the ring, isotopically labeled CO2 can be efficiently swapped in even at room temperature. Alternatively, reaction with aldehydes leads to alcohol formation.

Science, this issue p. 557

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