Core-Labeling (Radio) Synthesis of Phenols.
Colin F LynchJoseph W DowneyYongliang ZhangJacob M HookerMark D LevinPublished in: Organic letters (2023)
We report a method that enables the fast incorporation of carbon isotopes into the ipso carbon of phenols. Our approach relies on the synthesis of a 1,5-dibromo-1,4-pentadiene precursor, which upon lithium-halogen exchange followed by treatment with carbonate esters results in a formal [5 + 1] cyclization to form the phenol product. Using this strategy, we have prepared 12 1- 13 C-labeled phenols, show proof-of-concept for the labeling of phenols with carbon-14, and demonstrate phenol synthesis directly from cyclotron-produced [ 11 C]CO 2 .
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