title: Transition-metal-free synthesis of unsymmetrical diaryl chalcogenides from arenes and diaryl dichalcogenides.
abstract: A transition-metal-free synthetic method has been developed for the synthesis of unsymmetrical diaryl chalcogenides (S, Se, and Te) from diaryl dichalcogenides and arenes under oxidative conditions by using potassium persulfate at room temperature. Variously substituted arenes such as anisole, thioanisole, diphenyl ether, phenol, naphthol, di- and trimethoxy benzenes, xylene, mesitylene, N,N-dimethylaniline, bromine-substituted arenes, naphthalene, and diaryl dichalcogenides underwent carbon-chalcogen bond-forming reaction to give unsymmetrical diaryl chalcogenides in trifluoroacetic acid. To understand the mechanistic part of the reaction, a detailed in situ characterization of the intermediates has been carried out by (77)Se NMR spectroscopy by using diphenyl diselenide as the substrate. (77)Se NMR study suggests that electrophilic species ArE(+) is generated by the reaction of diaryl dichalcogenide with persulfate in trifluoroacetic acid. The electrophilic attack of arylchalcogenium ion on the arene may be responsible for the formation of the aryl-chalcogen bond.
authors: Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, MP 462 023, India.
authors: Ch Durga
authors: ChD
authors: Prasad
authors: Shah Jaimin
authors: SJ
authors: Balkrishna
authors: Amit
authors: A
authors: Kumar
authors: Bhagat Singh
authors: BS
authors: Bhakuni
authors: Kaustubh
authors: K
authors: Shrimali
authors: Soumava
authors: S
authors: Biswas
authors: Sangit
authors: S
authors: Kumar
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D018011:Chalcogens / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D028561:Transition Elements / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000814:Aniline Compounds; D018011:Chalcogens; D028561:Transition Elements; D014269:Trifluoroacetic Acid