{"title":"Ligand-Controlled Ni-Catalyzed Regiodivergent Hydrocyanation of Unactivated Alkynes toward Linear and Branched Vinyl Nitriles","authors":"Jiangkai Ma, Anjiang Qiao, Binglei Wang, Zhongxian Li, Fengqian Zhao, Junliang Wu","doi":"10.1021/acscatal.4c07739","DOIUrl":null,"url":null,"abstract":"In this paper, we have developed an efficient Ni-catalyzed highly regioselective and stereoselective hydrocyanation of alkynes and Zn(CN)<sub>2</sub>. By the control of different ligands, nickel-catalyzed regiodivergent hydrocyanation of terminal alkynes to linear and branched vinyl nitriles via <i>anti</i>-Markovnikov and Markovnikov additions was achieved. In addition, in this system, water or alcohol served as the hydrogen source, thus avoiding the <i>in-situ</i> generation of hydrogen cyanide in the reaction. A preliminary study of the mechanism was performed by deuterium labeling experiments and several control experiments.","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"14 1","pages":""},"PeriodicalIF":13.1000,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acscatal.4c07739","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
In this paper, we have developed an efficient Ni-catalyzed highly regioselective and stereoselective hydrocyanation of alkynes and Zn(CN)2. By the control of different ligands, nickel-catalyzed regiodivergent hydrocyanation of terminal alkynes to linear and branched vinyl nitriles via anti-Markovnikov and Markovnikov additions was achieved. In addition, in this system, water or alcohol served as the hydrogen source, thus avoiding the in-situ generation of hydrogen cyanide in the reaction. A preliminary study of the mechanism was performed by deuterium labeling experiments and several control experiments.
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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