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Reaction of Arynes with Sulfoxides

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journal contribution
posted on 06.03.2015, 00:00 by Hong-Ying Li, Li-Juan Xing, Mei-Mei Lou, Han Wang, Rui-Hua Liu, Bin Wang
A S–O bond insertion reaction of sulfoxides with arynes is reported. This reaction represents a rare instance of semipolar single bond insertion in aryne chemistry. The study of mechanism indicates that a sulfur ylide triggered by aryne is the key intermediate, which further transfers its methylene group to carbonyl compounds to give epoxides and thioethers through a sequential process.