A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis

[Image: see text] Manipulating carbon-centered radicals to add to electron-deficient systems is a well-precedented process. By coupling the Fe(II)-mediated Fenton reaction with the Fe(III)-mediated single-electron oxidation of anisolic compounds, we demonstrate how electron-rich carbon-centered radi...

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Autores principales: III, Robert Crowley, Lujan, Berkley, Martinez, Alex, Manasi, Roni, DeBow, Justin D., Kou, Kevin G. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10629232/
https://www.ncbi.nlm.nih.gov/pubmed/37847050
http://dx.doi.org/10.1021/acs.joc.3c01505
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author III, Robert Crowley
Lujan, Berkley
Martinez, Alex
Manasi, Roni
DeBow, Justin D.
Kou, Kevin G. M.
author_facet III, Robert Crowley
Lujan, Berkley
Martinez, Alex
Manasi, Roni
DeBow, Justin D.
Kou, Kevin G. M.
author_sort III, Robert Crowley
collection PubMed
description [Image: see text] Manipulating carbon-centered radicals to add to electron-deficient systems is a well-precedented process. By coupling the Fe(II)-mediated Fenton reaction with the Fe(III)-mediated single-electron oxidation of anisolic compounds, we demonstrate how electron-rich carbon-centered radicals can react with electron-rich arenes through a radical-polar cascade pathway. This bioinspired approach produces diarylmethane derivatives from simple unfunctionalized precursors.
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spelling pubmed-106292322023-11-08 A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis III, Robert Crowley Lujan, Berkley Martinez, Alex Manasi, Roni DeBow, Justin D. Kou, Kevin G. M. J Org Chem [Image: see text] Manipulating carbon-centered radicals to add to electron-deficient systems is a well-precedented process. By coupling the Fe(II)-mediated Fenton reaction with the Fe(III)-mediated single-electron oxidation of anisolic compounds, we demonstrate how electron-rich carbon-centered radicals can react with electron-rich arenes through a radical-polar cascade pathway. This bioinspired approach produces diarylmethane derivatives from simple unfunctionalized precursors. American Chemical Society 2023-10-17 /pmc/articles/PMC10629232/ /pubmed/37847050 http://dx.doi.org/10.1021/acs.joc.3c01505 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 III, Robert Crowley
Lujan, Berkley
Martinez, Alex
Manasi, Roni
DeBow, Justin D.
Kou, Kevin G. M.
A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis
title A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis
title_full A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis
title_fullStr A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis
title_full_unstemmed A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis
title_short A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis
title_sort fenton approach to aromatic radical cations and diarylmethane synthesis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10629232/
https://www.ncbi.nlm.nih.gov/pubmed/37847050
http://dx.doi.org/10.1021/acs.joc.3c01505
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