Zhen-Zhen Xie , Yu Zheng , Zi-Hao Liao , Chu-Ping Yuan , Ming-Zhi Li , Ke-Yi Deng , Hao-Yue Xiang , Kai Chen , Hua Yang
{"title":"Photoredox-catalyzed hydrogenation of alkenes assisted by an in situ generated PPh3(OH) radical and acetic acid†","authors":"Zhen-Zhen Xie , Yu Zheng , Zi-Hao Liao , Chu-Ping Yuan , Ming-Zhi Li , Ke-Yi Deng , Hao-Yue Xiang , Kai Chen , Hua Yang","doi":"10.1039/d4qo00661e","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, a practical, mild and convenient strategy was disclosed for the hydrogenation of alkenes under photocatalytic conditions through a HAT/protonation process. A combination of experimental and computational studies suggested that water was activated by a phosphine radical cation to generate the critical intermediate, the PR<sub>3</sub>(OH) radical, which acted as a “free” hydrogen atom to facilitate the initial HAT process.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"11 15","pages":"Pages 4187-4193"},"PeriodicalIF":0.0000,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412924004315","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/6/7 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, a practical, mild and convenient strategy was disclosed for the hydrogenation of alkenes under photocatalytic conditions through a HAT/protonation process. A combination of experimental and computational studies suggested that water was activated by a phosphine radical cation to generate the critical intermediate, the PR3(OH) radical, which acted as a “free” hydrogen atom to facilitate the initial HAT process.