Combined Gold and Photoredox Catalysis: Synthesis of 3‐Alkenyl‐2<i>H</i>‐Indazoles from 2‐Alkynylazobenzenes

Abstract We disclose the intramolecular synthesis of 3‐alkenyl‐2 H ‐indazoles from 2‐alkynylazobenzenes, promoted by a dual catalysis using AuCl 3 and a ruthenium photocatalyst under visible light irradiation. This reaction proceeds through hydroamination of the alkynyl fragment. The yields are influenced by electronic factors. Control experiments suggest that both radical and polar mechanisms operate in parallel. This transformation involves C−N bond formation and a 1,2‐hydride shift. Additionally, derivatization was performed to demonstrate the versatility of this methodology.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2024-10-16
DOI
https://doi.org/10.1002/adsc.202400990
Citations
3
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.75

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article

Combined Gold and Photoredox Catalysis: Synthesis of 3‐Alkenyl‐2H‐Indazoles from 2‐Alkynylazobenzenes

Estı́baliz Merino, Clara Mañas
3 citations
Advanced Synthesis & Catalysis
Catalytic Alkyne Reactions
0.75
article

Combined Gold and Photoredox Catalysis: Synthesis of 3‐Alkenyl‐2H‐Indazoles from 2‐Alkynylazobenzenes

Estı́baliz Merino, Clara Mañas
article en
3 citations

Abstract

Abstract We disclose the intramolecular synthesis of 3‐alkenyl‐2 H ‐indazoles from 2‐alkynylazobenzenes, promoted by a dual catalysis using AuCl 3 and a ruthenium photocatalyst under visible light irradiation. This reaction proceeds through hydroamination of the alkynyl fragment. The yields are influenced by electronic factors. Control experiments suggest that both radical and polar mechanisms operate in parallel. This transformation involves C−N bond formation and a 1,2‐hydride shift. Additionally, derivatization was performed to demonstrate the versatility of this methodology.

Advanced Synthesis & CatalysisVol. 367(1)
Universidad de Alcalá (ES), Instituto Ramón y Cajal de Investigación Sanitaria (ES)
Comunidad de Madrid, Ministerio de Ciencia e Innovación, Universidad de Alcalá
Openalex Percentile: Top 32%
Catalytic Alkyne Reactions
0.75
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