{"title":"Gold-Catalyzed Intermolecular 1,2-Difunctionalization of Alkynes with Aryl Iodides","authors":"Lizhu Zhang, , , Gang Li, , , Jiawen Wu, , , Rongjie Yang, , , Shuang Luo*, , and , Zhonghua Xia*, ","doi":"10.1021/acscatal.5c03719","DOIUrl":null,"url":null,"abstract":"<p >Compared with traditional transition metals, gold-catalyzed 1,2-difunctionalization of C–C multiple bonds has introduced a new paradigm. Herein, we report an unexplored gold-catalyzed intermolecular 1,2-difunctionalization of alkynes with aryl iodides in an EtOH/H<sub>2</sub>O mixture, furnishing a variety of α-aryl ketones, overcoming challenges such as facile hydrofunctionalization and direct cross-coupling. Under the influence of the hemilabile MeDalphos ligand gold catalyst, various alkynes underwent 1,2-difunctionalization with different aryl iodides, achieving a high efficiency and good regioselectivity to form α-aryl ketones in a one-pot reaction. This approach eliminates the need for strong external oxidants and the photocatalytic activation of aryl diazonium salts. Mechanistic and theoretical studies support a reaction pathway that effectively integrates the oxidative addition of aryl iodides and the π-activation of alkynes in gold(I)/gold(III) catalysis.</p>","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"15 19","pages":"16731–16739"},"PeriodicalIF":13.1000,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acscatal.5c03719","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
Compared with traditional transition metals, gold-catalyzed 1,2-difunctionalization of C–C multiple bonds has introduced a new paradigm. Herein, we report an unexplored gold-catalyzed intermolecular 1,2-difunctionalization of alkynes with aryl iodides in an EtOH/H2O mixture, furnishing a variety of α-aryl ketones, overcoming challenges such as facile hydrofunctionalization and direct cross-coupling. Under the influence of the hemilabile MeDalphos ligand gold catalyst, various alkynes underwent 1,2-difunctionalization with different aryl iodides, achieving a high efficiency and good regioselectivity to form α-aryl ketones in a one-pot reaction. This approach eliminates the need for strong external oxidants and the photocatalytic activation of aryl diazonium salts. Mechanistic and theoretical studies support a reaction pathway that effectively integrates the oxidative addition of aryl iodides and the π-activation of alkynes in gold(I)/gold(III) catalysis.
期刊介绍：
ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels.
The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
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