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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2019
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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. |
format | Online Article Text |
id | pubmed-6863597 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT tanwarlalita synthesisofbenzylicalcoholsbychoxidation AT borgeljonas synthesisofbenzylicalcoholsbychoxidation AT rittertobias synthesisofbenzylicalcoholsbychoxidation |