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DOI: 10.1055/a-2757-2765
Light-Induced Regioselective 6-Endo versus 5-Exo Cycloisomerization of o-Alkynylbenzoic Acids
Authors
Funding Information The authors would like to thank Sorbonne Université, the Centre National de la Recherche Scientifique (CNRS), the Institut Universitaire de France (IUF), and Collège de France for their financial support as well as the Agence Nationale de la Recherche (Grant No. ANR-20-CE07-0038 LuxOr for providing a PhD grant to M.B.M.).
Dedication
Dedicated to Paul Knochel, the Kaiser of C–M bonds.
Abstract
Regioselectivity of the gold(I)-catalyzed cycloisomerization of o-alkynyl benzoic acids is significantly influenced by blue LEDs irradiation. In particular, the reaction exhibits higher selectivity toward the 6-endo regioisomer when irradiated with blue light, whereas the 5-exo product is obtained as the major product in the absence of light. These findings prompted mechanistic inquiries that we sought to address through running the reactions in diverse conditions and also by studying the reactivity of the vinylgold(I) complexes that are formed as intermediates.
Keywords
Gold catalysis - Cycloisomerization - o-Alkynylbenzoic acids - Vinylgold(I) complex - Visible light activation - Regioselectivity - Isocoumarin - PhthalidePublication History
Received: 15 September 2025
Accepted after revision: 26 November 2025
Accepted Manuscript online:
26 November 2025
Article published online:
20 January 2026
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