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Synthesis of 3-Hydroxymethyl Isoindolinones via Cobalt-Catalyzed C(sp2)–H Carbonylation of Phenylglycinol Derivatives

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    Synthesis of 3-Hydroxymethyl Isoindolinones via Cobalt-Catalyzed C(sp2)–H Carbonylation of Phenylglycinol Derivatives
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    Organic Letters

    Cite this: Org. Lett. 2020, 22, 7, 2720–2723
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    https://doi.org/10.1021/acs.orglett.0c00672
    Published March 17, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    An efficient method for the synthesis of 3-hydroxymethyl isoindolinones via cobalt-catalyzed C(sp2)–H carbonylation of phenylglycinol derivatives using picolinamide as a traceless directing group is demonstrated. The reaction proceeds in the presence of a commercially available cobalt(II) tetramethylheptanedionate catalyst and employs DIAD as a “CO” surrogate. This synthetic route offers a broad substrate scope, excellent regioselectivity, and full preservation of the original stereochemistry. Besides, the developed method provides a pathway for accessing valuable enantiopure 3-substituted isoindolinone derivatives.

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    Organic Letters

    Cite this: Org. Lett. 2020, 22, 7, 2720–2723
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.0c00672
    Published March 17, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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