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Metal free cross-dehydrogenative N-N coupling of primary amides with Lewis basic amines

Author

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  • Subban Kathiravan

    (Linnaeus University
    Attana AB)

  • Prakriti Dhillon

    (Linnaeus University)

  • Tianshu Zhang

    (Linnaeus University)

  • Ian A. Nicholls

    (Linnaeus University)

Abstract

Hydrazides, N-N containing structural motifs, are important due to their presence in a wide variety of biologically significant compounds. While the homo N-N coupling of two NH moieties to form the hydrazide N-N bond is well developed, the cross-dehydrogenative hetero N-N coupling remains very unevolved. Here we present an efficient intermolecular N-N cross-coupling of a series of primary benzamides with broad range of Lewis basic primary and secondary amines using PhI(OAc)2 as both a terminal oxidant and a cross-coupling mediator, without the need for metal catalysts, high temperatures, and inert atmospheres, and with substantial potential for use in the late-stage functionalization of drugs.

Suggested Citation

  • Subban Kathiravan & Prakriti Dhillon & Tianshu Zhang & Ian A. Nicholls, 2024. "Metal free cross-dehydrogenative N-N coupling of primary amides with Lewis basic amines," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46890-9
    DOI: 10.1038/s41467-024-46890-9
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