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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Bibliographic Details
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
Subjects
Chemistry
Chemistry, Multidisciplinary
Communication
Physical Sciences
Science & Technology
FUNCTIONALIZATION
COMPLEX
HYDROGEN-ATOM ABSTRACTION
COUPLED ELECTRON-TRANSFER
ASYMMETRIC HYDROXYLATION
OXYGENATION
BONDS
RADICALS
EFFICIENT
HYDROXYPHTHALIMIDE
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Summary: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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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b09496