Formation of 3-Alkynylidenephthalides by Gold(I)-Catalyzed Alkynylative Cyclization of <i>o</i>-Alkynylbenzoic Acids under Visible Light Irradiation
Herein, we report a Csp<sup>2</sup>-Csp cross-coupling process involving the merger of gold catalysis and visible light photocatalysis leading to the alkynylative cyclization of <i>o</i>-alkynyl benzoic acids. The corresponding and previously undescribed alkynylidenephthalide products were obtained as mixtures of <i>E</i>:<i>Z</i> isomers. The key C-C bond formation is based on the photoactivation of the oxidative addition of an alkynyliodide to a vinylgold(I) intermediate resulting from an initial 5-<i>exo</i>-dig cyclization pathway, as supported by mechanistic studies including DFT calculations.
Authors
- Louis Fensterbank (ORCID: https://orcid.org/0000-0003-0001-7120)
- Virginie Mouriès‐Mansuy (ORCID: https://orcid.org/0000-0003-1804-4848)
- Héloïse Dossmann (ORCID: https://orcid.org/0000-0003-4844-229X)
- Jorge C. Herrera‐Luna (ORCID: https://orcid.org/0000-0003-2992-7339)
- María Ballarín‐Marión
- Vincent Corcé (ORCID: https://orcid.org/0000-0003-2481-7608)
- Cyril Ollivier (ORCID: https://orcid.org/0000-0003-2416-4467)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Collège de France (FR)
- Sorbonne Université (FR)
- Institut Parisien de Chimie Moléculaire (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-11-06
- DOI
- https://doi.org/10.1021/acs.joc.4c01876
- Citations
- 6
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- Agence Nationale de la Recherche
- Generalitat Valenciana
- Centre National de la Recherche Scientifique
- Sorbonne Université
- Collège de France