{"title":"Brønsted Acid-Catalyzed Solvent-Controlled Regioselective Thiolation of 2-Furylcarbinols","authors":"Chunyu Zhang, Tianyu Lin, Qing Liu, Rui Hu, Weidong Rao","doi":"10.1039/d4qo01904k","DOIUrl":null,"url":null,"abstract":"A novel p-toluenesulfonic acid-catalyzed solvent-controlled regioselective thiolation of 2-furylcarbinols for the efficient and chemoselective preparation of densely functionalized furan- and lactone-based sulfides under mild metal-free conditions has been developed. By using thiols as nucleophiles in DCE at 80 °C, a new reactivity involving a cascade C5-selective nucleophilic substitution/protonation-hydration/C-S bond cleavage/thia-Michael addition leads to lactone-based sulfides rather than the known Piancatelli-type rearrangement products was revealed for the first time. This tunable thiolation protocol enables ready access to both furan- and lactone-based sulfide derivatives with excellent yields by the judicious choice of the reaction solvent.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"3 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo01904k","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
A novel p-toluenesulfonic acid-catalyzed solvent-controlled regioselective thiolation of 2-furylcarbinols for the efficient and chemoselective preparation of densely functionalized furan- and lactone-based sulfides under mild metal-free conditions has been developed. By using thiols as nucleophiles in DCE at 80 °C, a new reactivity involving a cascade C5-selective nucleophilic substitution/protonation-hydration/C-S bond cleavage/thia-Michael addition leads to lactone-based sulfides rather than the known Piancatelli-type rearrangement products was revealed for the first time. This tunable thiolation protocol enables ready access to both furan- and lactone-based sulfide derivatives with excellent yields by the judicious choice of the reaction solvent.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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