Journal of Organic Chemistry p. 1434 - 1443 (2013)
Update date:2022-09-26
Topics: Synthesis Catalyst Solvent Reagent Transition-metal-free Arenes Reaction Vessel Unsymmetrical diaryl chalcogenides Diaryl dichalcogenides
Prasad, Ch Durga
Balkrishna, Shah Jaimin
Kumar, Amit
Bhakuni, Bhagat Singh
Shrimali, Kaustubh
Biswas, Soumava
Kumar, Sangit
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 77Se NMR spectroscopy by using diphenyl diselenide as the substrate. 77Se 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.
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