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Photo-mediated selective deconstructive geminal dihalogenation of trisubstituted alkenes

Author

Listed:
  • Han Wang

    (National University of Singapore)

  • Ren Wei Toh

    (National University of Singapore)

  • Xiangcheng Shi

    (National University of Singapore)

  • Tonglin Wang

    (Northwest Normal University)

  • Xu Cong

    (National University of Singapore)

  • Jie Wu

    (National University of Singapore
    National University of Singapore (Suzhou) Research Institute)

Abstract

Selective deconstructive functionalization of alkenes, other than the well-established olefin metathesis and ozonolysis, to produce densely functionalized molecular scaffolds is highly attractive but challenging. Here we report an efficient photo-mediated deconstructive germinal dihalogenation of carbon-carbon double bonds. A wide range of geminal diiodoalkanes and bromo(iodo)alkanes (>40 examples) are directly prepared from various trisubstituted alkenes, including both cyclic and acyclic olefins. This C=C cleavage is highly chemoselective and produces geminal dihalide ketones in good yields. Mechanistic investigations suggest a formation of alkyl hypoiodites from benzyl alcohols and N-iodoimides, which undergo light-induced homolytic cleavage to generate active oxygen radical species.

Suggested Citation

  • Han Wang & Ren Wei Toh & Xiangcheng Shi & Tonglin Wang & Xu Cong & Jie Wu, 2020. "Photo-mediated selective deconstructive geminal dihalogenation of trisubstituted alkenes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-18274-2
    DOI: 10.1038/s41467-020-18274-2
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    Cited by:

    1. Chen Zhu & Huifeng Yue & Magnus Rueping, 2022. "Nickel catalyzed multicomponent stereodivergent synthesis of olefins enabled by electrochemistry, photocatalysis and photo-electrochemistry," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

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