Cesium Carbonate-Catalyzed Synthesis of Phosphorothioates via S‑Phosphination of Thioketones

Ze-Wei Chen, Annamalai Pratheepkumar, Rekha Bai, Yongyi Hu, Satpal Singh Badsara, Kuo-Wei Huang, Chin-Fa Lee

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

A highly efficient and environmentally-friendly base-mediated transition metal-free direct thiophlic catalytic approach has been reported for the synthesis of S-benzhydryl-phosphorothioates by reacting phosphite nucleophiles with diarylmethanethione. A wide variety of thioketones were coupled with different phosphite derivatives to provide the corresponding phosphorothioates in good to excellent yields. The control experiments, and density functional theory (DFT) calculations relies on the regio-selective thiophilic addition of phosphite nucleophile via umpolung protocols.
Original languageEnglish (US)
JournalChemical Communications
DOIs
StatePublished - Sep 2 2022

Bibliographical note

KAUST Repository Item: Exported on 2022-09-14
Acknowledgements: This work was financially supported by the Ministry of Science and Technology, Taiwan (Most 110-2113-M-005-014-MY3), National Chung Hsing University, i-Center for Advanced Science and Technology (iCAST), the “Innovation and Development Centre of Sustainable Agriculture (IDCSA)” from The Featured Areas Research Centre Program within the framework of the Higher Education Sprout Project by the Ministry of Education (MOE) in Taiwan and Science and Engineering Research Board-Department of Science. We are also grateful to the service of NOOR 2, Shaheen 2 High Performance Computing Facilities, and financial support from King Abdullah University of Science and Technology (KAUST).

ASJC Scopus subject areas

  • Materials Chemistry
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Ceramics and Composites
  • General Chemistry
  • Catalysis
  • Electronic, Optical and Magnetic Materials

Fingerprint

Dive into the research topics of 'Cesium Carbonate-Catalyzed Synthesis of Phosphorothioates via S‑Phosphination of Thioketones'. Together they form a unique fingerprint.

Cite this