Zhaoshan Wang , Huiying Liu , Tiantian Liu , Qixiang Wang , Youhao Wei , Xiaoguang Bao , Xinxin Wu
{"title":"Constructing less-conjugated olefins via unusual regioselective hydrogen atom transfer from acetals†","authors":"Zhaoshan Wang , Huiying Liu , Tiantian Liu , Qixiang Wang , Youhao Wei , Xiaoguang Bao , Xinxin Wu","doi":"10.1039/d4qo02099e","DOIUrl":null,"url":null,"abstract":"<div><div>Utilizing a regioselective hydrogen atom transfer (RHAT) strategy, this study demonstrates a triple RHAT process accompanied by C–O bond homolysis to generate unusual less-conjugated or <em>contra</em>-thermodynamic olefins, a transformation rarely documented in the literature. The key to this conversion is the uncommon RHAT from the secondary ether C–H bond, rather than the weaker tertiary acetal C–H bond. This protocol offers a diverse class of synthetically versatile, less-conjugated, or <em>contra</em>-thermodynamic olefins.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1911-1917"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-22","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/S2052412925000415","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/14 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Utilizing a regioselective hydrogen atom transfer (RHAT) strategy, this study demonstrates a triple RHAT process accompanied by C–O bond homolysis to generate unusual less-conjugated or contra-thermodynamic olefins, a transformation rarely documented in the literature. The key to this conversion is the uncommon RHAT from the secondary ether C–H bond, rather than the weaker tertiary acetal C–H bond. This protocol offers a diverse class of synthetically versatile, less-conjugated, or contra-thermodynamic olefins.