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A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides

Author

Listed:
  • Clément Jacob

    (Université libre de Bruxelles (ULB)
    University of Antwerp)

  • Hajar Baguia

    (Université libre de Bruxelles (ULB))

  • Amaury Dubart

    (Université libre de Bruxelles (ULB))

  • Samuel Oger

    (Université libre de Bruxelles (ULB))

  • Pierre Thilmany

    (Université libre de Bruxelles (ULB))

  • Jérôme Beaudelot

    (Université libre de Bruxelles (ULB)
    Université libre de Bruxelles (ULB))

  • Christopher Deldaele

    (Université libre de Bruxelles (ULB))

  • Stefano Peruško

    (Université libre de Bruxelles (ULB)
    University of Antwerp)

  • Yohann Landrain

    (Université libre de Bruxelles (ULB))

  • Bastien Michelet

    (Université libre de Bruxelles (ULB))

  • Samuel Neale

    (Ghent University, Tech Lane Ghent Science Park Campus A)

  • Eugénie Romero

    (Université libre de Bruxelles (ULB))

  • Cécile Moucheron

    (Université libre de Bruxelles (ULB))

  • Veronique Speybroeck

    (Ghent University, Tech Lane Ghent Science Park Campus A)

  • Cédric Theunissen

    (Université libre de Bruxelles (ULB))

  • Gwilherm Evano

    (Université libre de Bruxelles (ULB))

Abstract

A general anti-Baldwin radical 4-exo-dig cyclization from nitrogen-substituted alkynes is reported. Upon reaction with a heteroleptic copper complex in the presence of an amine and under visible light irradiation, a range of ynamides were shown to smoothly cyclize to the corresponding azetidines, useful building blocks in natural product synthesis and medicinal chemistry, with full control of the regioselectivity of the cyclization resulting from a unique and underrated radical 4-exo-dig pathway.

Suggested Citation

  • Clément Jacob & Hajar Baguia & Amaury Dubart & Samuel Oger & Pierre Thilmany & Jérôme Beaudelot & Christopher Deldaele & Stefano Peruško & Yohann Landrain & Bastien Michelet & Samuel Neale & Eugénie R, 2022. "A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-28098-x
    DOI: 10.1038/s41467-022-28098-x
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