Direct reversible decarboxylation from stable organic acids in dimethylformamide solution

  • Duanyang Kong
    Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
  • Patrick J. Moon
    Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
  • Erica K. J. Lui
    Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
  • Odey Bsharat
    Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
  • Rylan J. Lundgren
    Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.

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<jats:title> Simple swaps of CO <jats:sub>2</jats:sub> </jats:title> <jats:p> The loss of carbon dioxide (CO <jats:sub>2</jats:sub> ) from carboxylic acids is a common reaction in both biochemical and synthetic contexts, but it has generally involved catalysis or prolonged heating. Kong <jats:italic>et al.</jats:italic> now report that certain polar solvents, such as dimethylformamide, promote reversible CO <jats:sub>2</jats:sub> loss all by themselves from carboxylates bridged by one carbon to aromatic rings. With electron-withdrawing substituents on the ring, isotopically labeled CO <jats:sub>2</jats:sub> can be efficiently swapped in even at room temperature. Alternatively, reaction with aldehydes leads to alcohol formation. </jats:p> <jats:p> <jats:italic>Science</jats:italic> , this issue p. <jats:related-article xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="doi" issue="6503" page="557" related-article-type="in-this-issue" vol="369" xlink:href="10.1126/science.abb4129">557</jats:related-article> </jats:p>

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  • Science

    Science 369 (6503), 557-561, 2020-07-31

    American Association for the Advancement of Science (AAAS)

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