{"title":"Combined Gold and Photoredox Catalysis: Synthesis of 3‐Alkenyl‐2H‐Indazoles from 2‐Alkynylazobenzenes","authors":"Clara Mañas , Estíbaliz Merino","doi":"10.1002/adsc.202400990","DOIUrl":null,"url":null,"abstract":"<div><div>We disclose the intramolecular synthesis of 3‐alkenyl‐2<em>H</em>‐indazoles from 2‐alkynylazobenzenes, promoted by a dual catalysis using AuCl<sub>3</sub> 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.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 1","pages":"Article e202400990"},"PeriodicalIF":4.4000,"publicationDate":"2025-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400990","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1615415024006307","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
We disclose the intramolecular synthesis of 3‐alkenyl‐2H‐indazoles from 2‐alkynylazobenzenes, promoted by a dual catalysis using AuCl3 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.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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