Radical selenation of C(sp3)–H bonds to asymmetric selenides and mechanistic study. Issue 10 (20th January 2022)

• Record Type: Journal Article
• Authors: Wang, Xin; Lei, Jia; Guo, Sa; Zhang, Yan; Ye, Yong; Tang, Shi; Sun, Kai
• Is Part Of: Chemical communications. Volume 58:Issue 10(2022)
• Page Start: 1526
• Page End: 1529
• Publication Date: 2022-01-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc06323e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Herein, the oxidative radical selenation of C(sp 3 )–H bonds to asymmetric selenides was developed. Various C(sp 3 )–H bonds with ethers, thioethers, and toluene derivatives were found to be suitable substrates for this novel transformation. Abstract : Selenides are important structural motifs with a broad range of biological activities and versatile transformational abilities. In this study, a novel and mild method was developed for the facile synthesis of asymmetric selenides under metal-free conditions. The key features of this reaction include good functional-group tolerance, the use of readily available reagents and cheap, low-toxicity solvent, and amenability to gram-scale synthesis. The results of preliminary radical-trapping experiments and a kinetic isotope effect study support a radical process.