{"title":"通过苯基甘氨醇与二甲基亚砜的外部无氧化剂氧化缩合轻松合成乙烯基硫醚","authors":"","doi":"10.1016/j.tetlet.2024.155321","DOIUrl":null,"url":null,"abstract":"<div><div>Oxidative activation of C<img>O, C<img>N and C<img>C bonds has recently emerged as a powerful method for the synthesis of valuable organic compounds. However, these strategies have often required the metal catalysts and strong external oxidants. Herein, we report a new protocol for the convenient construction of vinyl sulfoxides from phenylglycinols and DMSO under basic conditions. Notably, DMSO was used not only as a methyl sulfoxide (−SOMe) reagent, but also as an oxidizing agent. The present system features mild metal- and external oxidant-free conditions, broad scope, and excellent functionality tolerance.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Facile synthesis of vinyl sulfoxides via external oxidant-free oxidative condensation of phenylglycinols with DMSO\",\"authors\":\"\",\"doi\":\"10.1016/j.tetlet.2024.155321\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Oxidative activation of C<img>O, C<img>N and C<img>C bonds has recently emerged as a powerful method for the synthesis of valuable organic compounds. However, these strategies have often required the metal catalysts and strong external oxidants. Herein, we report a new protocol for the convenient construction of vinyl sulfoxides from phenylglycinols and DMSO under basic conditions. Notably, DMSO was used not only as a methyl sulfoxide (−SOMe) reagent, but also as an oxidizing agent. The present system features mild metal- and external oxidant-free conditions, broad scope, and excellent functionality tolerance.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-10-11\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924004167\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004167","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
近来,CO、CN 和 CC 键的氧化活化已成为合成有价值有机化合物的有力方法。然而,这些方法通常需要金属催化剂和强外部氧化剂。在此,我们报告了一种在碱性条件下利用苯基甘氨醇和二甲基亚砜方便地构建乙烯基硫醚的新方法。值得注意的是,DMSO 不仅用作甲基亚砜 (-SOMe) 试剂,还用作氧化剂。本系统的特点是条件温和,不含金属和外部氧化剂,适用范围广,对官能度的耐受性极佳。
Facile synthesis of vinyl sulfoxides via external oxidant-free oxidative condensation of phenylglycinols with DMSO
Oxidative activation of CO, CN and CC bonds has recently emerged as a powerful method for the synthesis of valuable organic compounds. However, these strategies have often required the metal catalysts and strong external oxidants. Herein, we report a new protocol for the convenient construction of vinyl sulfoxides from phenylglycinols and DMSO under basic conditions. Notably, DMSO was used not only as a methyl sulfoxide (−SOMe) reagent, but also as an oxidizing agent. The present system features mild metal- and external oxidant-free conditions, broad scope, and excellent functionality tolerance.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.