{"title":"Difunctionalization of Sulfamate-Derived Cyclic Imines through Phosphine Catalysis","authors":"Yaping Wang, Bing Zheng*, Jiawei Liu, Siting Qu, Shicong Hou, Leijie Zhou* and Hongchao Guo*, ","doi":"10.1021/acs.orglett.5c01703","DOIUrl":null,"url":null,"abstract":"<p >With the use of alkynyl 1,2-diones as phosphine acceptors and H<sub>2</sub>O as a reaction partner, an unprecedented phosphine-catalyzed three-component difunctionalization of sulfamate-derived cyclic imines was achieved, providing a wide range of highly functionalized cyclic sulfonamide products in moderate to good yields. This protocol features a broad substrate scope and mild reaction conditions. It also represents a rare example of H<sub>2</sub>O serving as a substrate to participate in phosphine-catalyzed reactions. The reaction mechanism involves a tandem acyloxylation/cinnamoylation reaction.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 26","pages":"6942–6946"},"PeriodicalIF":5.0000,"publicationDate":"2025-06-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c01703","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
With the use of alkynyl 1,2-diones as phosphine acceptors and H2O as a reaction partner, an unprecedented phosphine-catalyzed three-component difunctionalization of sulfamate-derived cyclic imines was achieved, providing a wide range of highly functionalized cyclic sulfonamide products in moderate to good yields. This protocol features a broad substrate scope and mild reaction conditions. It also represents a rare example of H2O serving as a substrate to participate in phosphine-catalyzed reactions. The reaction mechanism involves a tandem acyloxylation/cinnamoylation reaction.
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.