{"title":"Palladium-Catalyzed Insertion of Allenes into Dithioacetals To Access 1,3-Dithioethers","authors":"Shoule Cai, Hongchi Liu, Yinjun Xie, Hanmin Huang","doi":"10.1021/acs.orglett.5c00257","DOIUrl":null,"url":null,"abstract":"Great efforts have been devoted to synthesizing dithioethers due to their unique pharmaceutical properties. While significant success has been achieved in the synthesis of 1,1-dithioethers and 1,2-dithioethers, a concise and efficient strategy for the direct construction of 1,3-dithioethers has not yet been established. Herein, we developed a palladium-catalyzed thiomethylthiolation of allenes with dithioacetals to access a wide range of 1,3-dithioethers through the simultaneous construction of one carbon–carbon bond and one carbon–sulfur bond. A dithioacetal-coordinated cationic palladium complex was isolated and characterized, which was considered the crucial intermediate for this palladium-catalyzed transformation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"66 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00257","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Great efforts have been devoted to synthesizing dithioethers due to their unique pharmaceutical properties. While significant success has been achieved in the synthesis of 1,1-dithioethers and 1,2-dithioethers, a concise and efficient strategy for the direct construction of 1,3-dithioethers has not yet been established. Herein, we developed a palladium-catalyzed thiomethylthiolation of allenes with dithioacetals to access a wide range of 1,3-dithioethers through the simultaneous construction of one carbon–carbon bond and one carbon–sulfur bond. A dithioacetal-coordinated cationic palladium complex was isolated and characterized, which was considered the crucial intermediate for this palladium-catalyzed transformation.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
