Torsional strain inversed chemoselectivity in a Pd-catalyzed atroposelective carbonylation reaction of dibenzothiophenium |
| |
| Authors: | Qiuchi Zhang Xiaoping Xue Biqiong Hong Zhenhua Gu |
| |
| Institution: | Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei Anhui 230026 P. R. China.; College of Materials and Chemical Engineering, Minjiang University, Fuzhou Fujian 350108 P. R. China |
| |
| Abstract: | A palladium-catalyzed enantioselective ring-opening/carbonylation of cyclic diarylsulfonium salts is reported. In comparison to thioethers, the sulfonium salts displayed high reactivity and enabled the reaction to be performed under mild conditions (room temperature). The steric repulsion of the two non-hydrogen substituents adjacent to the axis led cyclic diarylsulfonium salts to be distorted, which enabled the ring-opening reaction to proceed with significant preference for breaking the exocyclic C–S bond.Torsional strain inversed chemoselectivity: from bond a to bond b. |
| |
| Keywords: | |
|
|
