{"title":"通过Si-F键的形成,由酰基氟化物和硫硅烷直接合成各种硫酯。","authors":"Ryuki Takeuchi, , , Kento Ishida, , and , Norio Sakai*, ","doi":"10.1021/acs.joc.5c01677","DOIUrl":null,"url":null,"abstract":"<p >Herein it is described that the coupling reactions of aromatic and aliphatic acyl fluorides with phenyl trimethylsilyl sulfide proceeded smoothly under neat conditions to produce thioester derivatives. The addition of a catalytic amount of typical bases, such as triethylamine (Et<sub>3</sub>N) and potassium butoxide (KO<sup><i>t</i></sup>Bu), effectively activates thiosilanes, which could facilitate the coupling reactions of aroyl fluorides with a variety of aryl/alkyl thiosilanes containing an alkyl group, a halogen, an ester, or a heterocyclic ring to produce a variety of thioesters in practical yields.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 41","pages":"14664–14672"},"PeriodicalIF":3.6000,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.joc.5c01677","citationCount":"0","resultStr":"{\"title\":\"Direct Synthesis of Various Thioesters from Acyl Fluorides and Thiosilanes through the Assistance of a Si–F Bond Formation\",\"authors\":\"Ryuki Takeuchi, , , Kento Ishida, , and , Norio Sakai*, \",\"doi\":\"10.1021/acs.joc.5c01677\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Herein it is described that the coupling reactions of aromatic and aliphatic acyl fluorides with phenyl trimethylsilyl sulfide proceeded smoothly under neat conditions to produce thioester derivatives. The addition of a catalytic amount of typical bases, such as triethylamine (Et<sub>3</sub>N) and potassium butoxide (KO<sup><i>t</i></sup>Bu), effectively activates thiosilanes, which could facilitate the coupling reactions of aroyl fluorides with a variety of aryl/alkyl thiosilanes containing an alkyl group, a halogen, an ester, or a heterocyclic ring to produce a variety of thioesters in practical yields.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"90 41\",\"pages\":\"14664–14672\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-10-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.acs.org/doi/pdf/10.1021/acs.joc.5c01677\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.5c01677\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.5c01677","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Direct Synthesis of Various Thioesters from Acyl Fluorides and Thiosilanes through the Assistance of a Si–F Bond Formation
Herein it is described that the coupling reactions of aromatic and aliphatic acyl fluorides with phenyl trimethylsilyl sulfide proceeded smoothly under neat conditions to produce thioester derivatives. The addition of a catalytic amount of typical bases, such as triethylamine (Et3N) and potassium butoxide (KOtBu), effectively activates thiosilanes, which could facilitate the coupling reactions of aroyl fluorides with a variety of aryl/alkyl thiosilanes containing an alkyl group, a halogen, an ester, or a heterocyclic ring to produce a variety of thioesters in practical yields.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.