A new approach to large scale production of dimethyl sulfone: a promising and strong recyclable solvent for ligand-free Cu-catalyzed C–C cross-coupling reactions. Issue 6 (10th March 2020)

• Record Type: Journal Article
• Authors: Cheng, Shen; Wei, Wei; Zhang, Xingyu; Yu, Hewei; Huang, Mingming; Kazemnejadi, Milad
• Is Part Of: Green chemistry. Volume 22:Issue 6(2020)
• Page Start: 2069
• Page End: 2076
• Publication Date: 2020-03-10
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c9gc04374h
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : Dimethyl sulfone (DMSN or MSM) was prepared via efficient oxidation of dimethyl sulfoxide and used and developed as an efficient, viscose, and recyclable solvent for ligand-free CuI-catalyzed Heck, Suzuki, and Sonogashira cross-coupling reactions. Abstract : Dimethyl sulfone (DMSN) was easily prepared through efficient oxidation of dimethyl sulfoxide (DMSO) and used as a strong and green solvent for organic reactions. A mixture of HNO3 /NaOCl was used as an oxidizing agent for efficient oxidation of DMSO to DMSN. The effect of DMSN was evaluated for copper-catalyzed coupling reactions. It is worth noting that DMSN could play the role of a ligand for copper ions. A general survey was accomplished for various types of C–C cross-coupling reactions catalyzed by CuI in DMSN in the absence of any ligand. Moderate to good yields were achieved for Sonogashira, Heck, and Suzuki cross-coupling reactions. Finally, DMSN was recovered and reused for several consecutive runs without any loss of its activity.