N-Heterocyclic Nitrenium-Catalyzed Photohomolysis of CF<sub>3</sub>SO<sub>2</sub>Cl for Alkene Trifluoromethylation
Xiaojian Ren, Peng-Wei Liao, Sheng He, Zhixiang Wang, Xiang‐Yu Chen
Abstract
N-Heterocyclic nitreniums (NHNs) have been utilized as Lewis acid catalysts to activate substrates with lone pairs. Alternative to their conventional applications, we have discovered that NHNs can also serve as charge transfer complex catalysts. Herein, we present another potential of NHNs by utilizing a weak interaction between NHNs and CF 3 SO 2 Cl. The method promotes CF 3 SO 2 Cl to undergo photohomolysis, resulting in the CF 3 radical. Mechanistic studies suggested that the weak interaction could be due to the π-hole effect of NHNs.
Topics & Concepts
ChemistryAlkeneCatalysisTrifluoromethylationLewis acids and basesLone pairCombinatorial chemistryComputational chemistryMedicinal chemistryOrganic chemistryMoleculeAlkylTrifluoromethylFluorine in Organic ChemistryRadical Photochemical ReactionsInorganic Fluorides and Related Compounds