Transition‐Metal‐Free and Site‐Selective Selenylation of Heterocyclic N‐Oxides in Anisole as a Green Solvent. Issue 31 (9th June 2020)

• Record Type: Journal Article
• Authors: Lee, Suk Hun; Kwon, Na Yeon; Lee, Ji Yoon; An, Won; Jung, Young Hoon; Mishra, Neeraj Kumar; Ghosh, Prithwish; Park, Jung Su; Kim, In Su
• Is Part Of: European journal of organic chemistry. Issue 31(2020)
• Page Start: 4886
• Page End: 4892
• Publication Date: 2020-06-09
• Subjects: Chalcogenation -- Heterocycles -- N‐Oxides -- Selenium -- Transition‐metal‐free; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000610
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Transition‐metal‐free and site‐selective C–H selenylation of heterocyclic N ‐oxides with diselenides is described. This method can be also applied for the formation of C2‐sulfenylated and C2‐tellurinated quinoline derivatives. Notably, the simple reaction conditions with the use of anisole as a green solvent have been employed in this coupling reaction. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process. The synthetic transformations demonstrate the utility of the developed method. Abstract : An environmentally benign protocol for the C–H selenylation of heterocyclic N ‐oxides with diselenides in anisole as one of the greenest solvent is described. Application of this method for the formation of C2‐sulfenylated and C2‐tellurinated quinoline derivatives is also possible.