{"title":"Carboxylate-Directed Oxidative Annulation via C(Alkenyl)－H Activation/Double Alkyne Insertion/1,4-Pd Migration: Synthesis of Functionalized Naphthalenes","authors":"Chih-Ming Chou, Cheng-Hao Fu, Manjaly J. Ajitha, Veerabhushanam Kadiyala, Yu-Chun Wang, Tzu-Yu Hsu, I-Hsuan Sung, Kuo-wei Huang","doi":"10.1002/adsc.202400973","DOIUrl":null,"url":null,"abstract":"A palladium-catalyzed double consecutive C(alkenyl)–H activation/alkyne insertion method utilizing a free carboxylic acid as a directing group in the preparation of functionalized naphthalenes is reported. The reaction mechanism involves a sequence of the C (alkenyl)−H activation/alkyne insertion/1,4-palladium migration/reductive elimination steps. The second alkyne insertion occurred at the phenyl ring of the intermediate generated from the first alkyne insertion via 1,4-palladium migration, which is an uncommon case in typical C–H activation/alkyne insertion chemistry, providing functionalized naphthalene products. Additionally, the kinetic studies and control experiments as well as density functional theory (DFT) studies are also investigated to elucidate the reaction mechanism.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"22 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202400973","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
A palladium-catalyzed double consecutive C(alkenyl)–H activation/alkyne insertion method utilizing a free carboxylic acid as a directing group in the preparation of functionalized naphthalenes is reported. The reaction mechanism involves a sequence of the C (alkenyl)−H activation/alkyne insertion/1,4-palladium migration/reductive elimination steps. The second alkyne insertion occurred at the phenyl ring of the intermediate generated from the first alkyne insertion via 1,4-palladium migration, which is an uncommon case in typical C–H activation/alkyne insertion chemistry, providing functionalized naphthalene products. Additionally, the kinetic studies and control experiments as well as density functional theory (DFT) studies are also investigated to elucidate the reaction mechanism.
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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