Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 4, Pages 1434-1443Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo302480j
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- Department of Science and Technology (DST), New Delhi, India
- Department of Atomic Energy (DAE-BRNS) Mumbai
- Defence Research and Development Organization (DRDO) New Delhi
- IISER Bhopal
- CSIR-UGC New Delhi
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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 Se-77 NMR spectroscopy by using diphenyl diselenide as the substrate. Se-77 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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