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.

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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
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article

Gold‐Catalyzed Cyclization of Indole‐Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles

Chengting Wang, Jingrui He, Jorge Escorihuela, Haibo Mei et al.
European Journal of Organic Chemistry
Catalytic Alkyne Reactions
article

Gold‐Catalyzed Cyclization of Indole‐Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles

Chengting Wang, Jingrui He, Jorge Escorihuela, Haibo Mei, Jianlin Han
article en

Abstract

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.

European Journal of Organic Chemistry
Universitat de València (ES), Nanjing Forestry University (CN)
Openalex Percentile: Top 24%
Catalytic Alkyne Reactions
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