Synthesis of o-Aryloxy Triarylsulfonium Salts via Aryne Insertion into Diaryl Sulfoxides.
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.
Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.
Xiaojin
X
Li
Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.
Yan
Y
Sun
Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.
Xin
X
Huang
Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.
Lei
L
Zhang
Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.
Lichun
L
Kong
Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.|State Key Laboratory of Fine Chemicals, Dalian University of Technology , Dalian 116024, China.
Bo
0000-0002-8237-6698
B
Peng