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Published on: February 24, 2015
Synthesis of o-Aryloxy Triarylsulfonium Salts via Aryne Insertion into Diaryl Sulfoxides
Xiaojin Li1, Yan Sun1, Xin Huang1
1Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.
Abstract:
The aryne insertion into "S═O" bond has been validated recently. This technology is elusively applied to the synthesis of thioethers. In contrast to the reported cases, the reaction described furnished o-aryloxy triarylsulfonium salts, in lieu of thioethers, in good to excellent yields. The reaction is also featured by its exquisite regioselectivity, broad substrate scope, and mild conditions (25 °C). Preliminary mechanistic studies suggest that the reaction probably proceeds in a sequential [2 + 2] cycloaddtion/O-arylation/protonation pathway.
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