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Synthesis
DOI: 10.1055/a-2757-2765
Paper

Light-induced Regioselective 6-endo versus 5-exo Cycloisomerization of o-Alkynylbenzoic Acids

Autoren

  • Maria Ballarin-Marion

    1   Institut Parisien de Chimie Moléculaire, Sorbonne Universite, Paris, France (Ringgold ID: RIN27063)

  • Riccardo Mobili

    2   Institut Parisien de Chimie Moléculaire, Sorbonne Université, Paris, France (Ringgold ID: RIN27063)

  • Geoffrey Gontard

    2   Institut Parisien de Chimie Moléculaire, Sorbonne Université, Paris, France (Ringgold ID: RIN27063)

  • Jeremy Forte

    1   Institut Parisien de Chimie Moléculaire, Sorbonne Universite, Paris, France (Ringgold ID: RIN27063)

  • Cyril Ollivier

    2   Institut Parisien de Chimie Moléculaire, Sorbonne Université, Paris, France (Ringgold ID: RIN27063)

  • Virginie Mouries-Mansuy

    1   Institut Parisien de Chimie Moléculaire, Sorbonne Universite, Paris, France (Ringgold ID: RIN27063)

  • Louis Fensterbank 

    3   Laboratoire d'Activation Moléculaire, Collège de France, Paris, France (Ringgold ID: RIN52843)

Gefördert durch: Agence Nationale de la Recherche ANR-20-CE07-0038 LuxOr
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Regioselectivity of the gold(I)-catalyzed cycloisomerization of o-alkynyl benzoic acids is significantly influenced by blue LEDs irradiation. In particular, the reaction exhibits a higher selectivity towards the 6-endo regioisomer when irradiated with blue light, whereas the 5-exo product is obtained as major product in the absence of light. These findings prompted mechanistic inquiries that we sought to address through running reactions in diverse conditions and also by studying the reactivity of the vinylgold(I) complexes that are formed as intermediates.



Publikationsverlauf

Eingereicht: 15. September 2025

Angenommen nach Revision: 26. November 2025

Accepted Manuscript online:
26. November 2025

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