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Synthesis of Benzylic Alcohols by C–H Oxidation

[Image: see text] Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(metha...

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Autores principales: Tanwar, Lalita, Börgel, Jonas, Ritter, Tobias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6863597/
https://www.ncbi.nlm.nih.gov/pubmed/31689095
http://dx.doi.org/10.1021/jacs.9b09496
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author Tanwar, Lalita
Börgel, Jonas
Ritter, Tobias
author_facet Tanwar, Lalita
Börgel, Jonas
Ritter, Tobias
author_sort Tanwar, Lalita
collection PubMed
description [Image: see text] Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals.
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spelling pubmed-68635972019-11-20 Synthesis of Benzylic Alcohols by C–H Oxidation Tanwar, Lalita Börgel, Jonas Ritter, Tobias J Am Chem Soc [Image: see text] Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals. American Chemical Society 2019-11-05 2019-11-13 /pmc/articles/PMC6863597/ /pubmed/31689095 http://dx.doi.org/10.1021/jacs.9b09496 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Tanwar, Lalita
Börgel, Jonas
Ritter, Tobias
Synthesis of Benzylic Alcohols by C–H Oxidation
title Synthesis of Benzylic Alcohols by C–H Oxidation
title_full Synthesis of Benzylic Alcohols by C–H Oxidation
title_fullStr Synthesis of Benzylic Alcohols by C–H Oxidation
title_full_unstemmed Synthesis of Benzylic Alcohols by C–H Oxidation
title_short Synthesis of Benzylic Alcohols by C–H Oxidation
title_sort synthesis of benzylic alcohols by c–h oxidation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6863597/
https://www.ncbi.nlm.nih.gov/pubmed/31689095
http://dx.doi.org/10.1021/jacs.9b09496
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