Synthesis of Benzylic Alcohols by C–H Oxidation

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) perox...

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Published inJournal of the American Chemical Society Vol. 141; no. 45; pp. 17983 - 17988
Main Authors Tanwar, Lalita, Börgel, Jonas, Ritter, Tobias
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.11.2019
Amer Chemical Soc
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Abstract 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.
AbstractList 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.
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.
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.
Author Tanwar, Lalita
Börgel, Jonas
Ritter, Tobias
AuthorAffiliation Max-Planck-Institut für Kohlenforschung
AuthorAffiliation_xml – name: Max-Planck-Institut für Kohlenforschung
Author_xml – sequence: 1
  givenname: Lalita
  surname: Tanwar
  fullname: Tanwar, Lalita
– sequence: 2
  givenname: Jonas
  orcidid: 0000-0001-5301-8579
  surname: Börgel
  fullname: Börgel, Jonas
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  givenname: Tobias
  orcidid: 0000-0002-6957-450X
  surname: Ritter
  fullname: Ritter, Tobias
  email: ritter@mpi-muelheim.mpg.de
BackLink https://www.ncbi.nlm.nih.gov/pubmed/31689095$$D View this record in MEDLINE/PubMed
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Issue 45
Keywords FUNCTIONALIZATION
COMPLEX
HYDROGEN-ATOM ABSTRACTION
COUPLED ELECTRON-TRANSFER
ASYMMETRIC HYDROXYLATION
OXYGENATION
BONDS
RADICALS
EFFICIENT
HYDROXYPHTHALIMIDE
Language English
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Snippet 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...
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...
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...
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SubjectTerms Chemistry
Chemistry, Multidisciplinary
Communication
Physical Sciences
Science & Technology
Title Synthesis of Benzylic Alcohols by C–H Oxidation
URI http://dx.doi.org/10.1021/jacs.9b09496
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