Formation of 3-Alkynylidenephthalides by Gold(I)-Catalyzed Alkynylative Cyclization of o-Alkynylbenzoic Acids under Visible Light Irradiation
Year: 2024
Type: article
Abstract: Herein, we report a Csp 2 –Csp cross-coupling process involving the merger of gold catalysis and visible light photocatalysis leading to the alkynylative cyclization of o -alkynyl benzoic acids. The corresponding and previously undescribed alkynylidenephthalide products were obtained as mixtures of E: Z 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- exo -dig cyclization pathway, as supported by mechanistic studies including DFT calculations.
Source: The Journal of Organic Chemistry
Language: English
Topic: Catalytic Alkyne Reactions
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4404108503