Gold-Catalyzed Cascade Cyclization and Amidation of 2-Alkynyl Arylazides To Access 3-Amidoindoles

A gold-catalyzed cyclization and amidation of 2-alkynyl arylazides with nitriles and water is described. This protocol affords structurally diverse 3-amidoindoles in moderate to excellent yields under mild reaction conditions via the key benzene-fused α-imino gold carbene intermediate. Mechanistic studies reveal that the oxygen atom in the amide group is derived from water.

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Publication Details

Journal
Organic Letters
Published
2025-11-27
DOI
https://doi.org/10.1021/acs.orglett.5c04581
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Gold-Catalyzed Cascade Cyclization and Amidation of 2-Alkynyl Arylazides To Access 3-Amidoindoles

Anyuan Cao, Chengfeng Zhu, Mengcheng Wang, Xiang Wu et al.
Organic Letters
Catalytic Alkyne Reactions
article

Gold-Catalyzed Cascade Cyclization and Amidation of 2-Alkynyl Arylazides To Access 3-Amidoindoles

Anyuan Cao, Chengfeng Zhu, Mengcheng Wang, Xiang Wu, Zhen-Yu Wang, Si-Ru Wang, Jianping Wu, Yanming Fu
article en

Abstract

A gold-catalyzed cyclization and amidation of 2-alkynyl arylazides with nitriles and water is described. This protocol affords structurally diverse 3-amidoindoles in moderate to excellent yields under mild reaction conditions via the key benzene-fused α-imino gold carbene intermediate. Mechanistic studies reveal that the oxygen atom in the amide group is derived from water.

Organic LettersVol. 27(49)
Hefei University of Technology (CN), Veterinary and Agrochemical Research Centre (BE), Ministry of Industry and Information Technology (CN)
Openalex Percentile: Top 72%
Catalytic Alkyne Reactions
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