Marcos López-Aguilar, Nicolás Ríos-Lombardía, Miguel Gallegos, Daniel Barrena-Espés, Joaquín García-Álvarez, Carmen Concellón, Vicente Del Amo
{"title":"Organocatalytic CS<sub>2</sub> insertion into epoxides in neat conditions: a straightforward approach for the efficient synthesis of Di- and tri-thiocarbonates.","authors":"Marcos López-Aguilar, Nicolás Ríos-Lombardía, Miguel Gallegos, Daniel Barrena-Espés, Joaquín García-Álvarez, Carmen Concellón, Vicente Del Amo","doi":"10.1039/d4cc05154h","DOIUrl":null,"url":null,"abstract":"<p><p>The straightforward organocatalytic insertion of carbon disulfide (CS<sub>2</sub>) into epoxides using either choline chloride (<i>ChCl</i>) or tetrabutylammonium chloride (TBACl) is reported, for the first time, under solvent-free (neat) conditions. Fine-tuning of our system allowed us to obtain either dithiocarbonates (DTCs) or trithiocarbonates (TTCs) with high efficiency. Additionally, a mechanistic proposal is presented, supported by experimental evidence, DFT calculations and wavefunction analyses.</p>","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":" ","pages":""},"PeriodicalIF":4.3000,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4cc05154h","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The straightforward organocatalytic insertion of carbon disulfide (CS2) into epoxides using either choline chloride (ChCl) or tetrabutylammonium chloride (TBACl) is reported, for the first time, under solvent-free (neat) conditions. Fine-tuning of our system allowed us to obtain either dithiocarbonates (DTCs) or trithiocarbonates (TTCs) with high efficiency. Additionally, a mechanistic proposal is presented, supported by experimental evidence, DFT calculations and wavefunction analyses.
期刊介绍:
ChemComm (Chemical Communications) is renowned as the fastest publisher of articles providing information on new avenues of research, drawn from all the world''s major areas of chemical research.