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Photoinduced ynamide structural reshuffling and functionalization

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  • Mohana Reddy Mutra

    (Kaohsiung Medical University)

  • Jeh‐Jeng Wang

    (Kaohsiung Medical University
    Kaohsiung Medical University Hospital)

Abstract

The radical chemistry of ynamides has recently drawn the attention of synthetic organic chemists to the construction of various N-heterocyclic compounds. Nevertheless, the ynamide-radical chemistry remains a long-standing challenge for chemists due to its high reactivity, undesirable byproducts, severe inherent regio- and chemoselective problems. Importantly, the ynamide C(sp)-N bond fission remains an unsolved challenge. In this paper, we observe Photoinduced radical trigger regio- and chemoselective ynamide bond fission, structural reshuffling and functionalization of 2-alkynyl-ynamides to prepare synthetically inaccessible/challenging chalcogen-substituted indole derivatives with excellent step/atom economy. The key breakthroughs of this work includes, ynamide bond cleavage, divergent radical precursors, broad scope, easy to handle, larger-scale reactions, generation of multiple bonds (N-C(sp2), C(sp2)-C(sp2), C(sp2)-SO2R/C-SR, and C-I/C-Se/C-H) in a few minutes without photocatalysts, metals, oxidants, additives. Control experiments and 13C-labeling experiments supporting the conclusion that sulfone radicals contribute to ynamide structural reshuffling processes via a radical pathway.

Suggested Citation

  • Mohana Reddy Mutra & Jeh‐Jeng Wang, 2022. "Photoinduced ynamide structural reshuffling and functionalization," Nature Communications, Nature, vol. 13(1), pages 1-14, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30001-7
    DOI: 10.1038/s41467-022-30001-7
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    References listed on IDEAS

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    1. Linwei Zeng & Yuxin Lin & Jiaming Li & Hironao Sajiki & Hujun Xie & Sunliang Cui, 2020. "Skeletal reorganization divergence of N-sulfonyl ynamides," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
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