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Synthesis of Benzylic Alcohols by C-H Oxidation.

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.

SUBMITTER: Tanwar L

PROVIDER: S-EPMC6863597 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Synthesis of Benzylic Alcohols by C-H Oxidation.

Tanwar Lalita L Börgel Jonas J Ritter Tobias T

Journal of the American Chemical Society 20191105 45

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 t ...[more]

PMID: 31689095

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