Gold‐Catalyzed Cyclization of Indole‐Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles
A gold‐catalyzed intramolecular cyclization of indole‐tethered alkynes using Hantzsch ester (HE) and AgNTf 2 as additives has been developed, providing diverse functionalized exocyclic alkenyl tetrahydrocarbazoles in good to excellent yields. Control experiments and DFT studies indicate that the reaction proceeds via a 6‐ exo ‐dig cyclization pathway, with gold acetylide complexes as key intermediates and HE serving as a base. The reaction proceeds under mild conditions, shows broad functional‐group tolerance, and is amenable to scale‐up. Selected tetrahydrocarbazole products also exhibited moderate antifungal activity against two forest pathogenic fungi.
Authors
- Chengting Wang
- Jingrui He
- Jorge Escorihuela (ORCID: https://orcid.org/0000-0001-6756-0991)
- Haibo Mei (ORCID: https://orcid.org/0000-0002-2857-1935)
- Jianlin Han (ORCID: https://orcid.org/0000-0002-3817-0764)
Institutions
- Universitat de València (ES)
- Nanjing Forestry University (CN)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2026-10-05
- DOI
- https://doi.org/10.1002/ejoc.70895
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00