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Published on: February 20, 2020
Lewis Acid Promoted Vicinal Oxytrifluoromethylselenolation of Alkenes
Yang Li1, Shangbiao Zhang1, Yanan Wang1
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Sciences, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.
Abstract:
Herein, we have developed a metal-free, Lewis acid promoted vicinal oxytrifluoromethylselenolation of alkenes using trifluoromethyl selenoxides as electrophilic trifluoromethylselenolation reagents and alcohols as nucleophiles. With less steric and good nucleophilic solvents (such as ethanol and methol), Tf2O-catalyzed oxytrifluoromethylselenolation could be realized, while stoichiometric Tf2O was required to promote full transformation with less nucleophilic and steric solvents (such as isopropanol and tert-butanol). The reaction featured good substrate scope, functional group compatibility, and diastereoselectivity. This method could be further applied to oxytrifluoromethylselenolation, aminotrifluoromethylselenolation with stoichiometric nucleophiles under modified conditions. A mechanism involving a seleniranium ion was proposed based on the preliminary results.
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