Core-Labeling (Radio) Synthesis of Phenols

[Image: see text] 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 fo...

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Autores principales: Lynch, Colin F., Downey, Joseph W., Zhang, Yongliang, Hooker, Jacob M., Levin, Mark D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10563162/
https://www.ncbi.nlm.nih.gov/pubmed/37751441
http://dx.doi.org/10.1021/acs.orglett.3c02838
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author Lynch, Colin F.
Downey, Joseph W.
Zhang, Yongliang
Hooker, Jacob M.
Levin, Mark D.
author_facet Lynch, Colin F.
Downey, Joseph W.
Zhang, Yongliang
Hooker, Jacob M.
Levin, Mark D.
author_sort Lynch, Colin F.
collection PubMed
description [Image: see text] 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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spelling pubmed-105631622023-10-11 Core-Labeling (Radio) Synthesis of Phenols Lynch, Colin F. Downey, Joseph W. Zhang, Yongliang Hooker, Jacob M. Levin, Mark D. Org Lett [Image: see text] 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). American Chemical Society 2023-09-26 /pmc/articles/PMC10563162/ /pubmed/37751441 http://dx.doi.org/10.1021/acs.orglett.3c02838 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Lynch, Colin F.
Downey, Joseph W.
Zhang, Yongliang
Hooker, Jacob M.
Levin, Mark D.
Core-Labeling (Radio) Synthesis of Phenols
title Core-Labeling (Radio) Synthesis of Phenols
title_full Core-Labeling (Radio) Synthesis of Phenols
title_fullStr Core-Labeling (Radio) Synthesis of Phenols
title_full_unstemmed Core-Labeling (Radio) Synthesis of Phenols
title_short Core-Labeling (Radio) Synthesis of Phenols
title_sort core-labeling (radio) synthesis of phenols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10563162/
https://www.ncbi.nlm.nih.gov/pubmed/37751441
http://dx.doi.org/10.1021/acs.orglett.3c02838
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