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Cobalt-catalyzed divergent functionalization of N-sulfonyl amines via β-carbon elimination

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Abstract

This article demonstrates a catalytic method for C(aryl)—C(alkyl) bond functionalization of N-sulfonyl amines. A cobalt(III) catalyst was used to cleave the C—C bond via β-carbon elimination, providing a metallacycle intermediate. Subsequent allylation, amidation, or alkenylation of the intermediate led to divergent conversions in the presence of diverse coupling partners. when the coupling partner was a diene, an insertion-type functionalization was realized with an exclusive 1,3-regioselectivity, in which both of the fragments derived from N-sulfonyl amines were utilized.

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Acknowledgements

This work was supported by the “Pioneer” and “Leading Goose” R&D Program of Zhejiang (2022SDXHDX0006) and the Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang (2020R01004).

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Authors and Affiliations

  1. Department of Chemistry, Zhejiang University, Hangzhou, 310027, China

    Lun Xu

  2. Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, Hangzhou, 310024, China

    Lun Xu & Hang Shi

  3. Institute of Natural Sciences, Westlake Institute for Advanced Study, Hangzhou, 310024, China

    Hang Shi

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  1. Lun Xu
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  2. Hang Shi
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Correspondence to Hang Shi.

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Conflict of interest The authors declare no conflict of interest.

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Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Xu, L., Shi, H. Cobalt-catalyzed divergent functionalization of N-sulfonyl amines via β-carbon elimination. Sci. China Chem. 65, 2214–2218 (2022). https://doi.org/10.1007/s11426-022-1251-4

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  • DOI: https://doi.org/10.1007/s11426-022-1251-4

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