Anaerobic 1,2-/1,3-Hydroxytrifluoromethylation of Unactivated Alkenes Enabled by Photoexcited Nitroarenes
Cong Shi, Ruihua Liu, Zemin Wang, Chenxia Gao, Jiashu Chen, Hongyun Qin, Wenlong Shan, Wenli Zhuang, Nan Zhou, Xiangqian Li, Dayong Shi
Abstract
An anaerobic 1,2-/1,3-hydroxytrifluoromethylation of unactivated alkenes is described. This reaction proceeds in mild and environmentally friendly conditions without photocatalyst and metal catalyst, allowing access to a wide range of β- and γ-trifluoromethyl alcohols. Preliminary mechanistic investigations indicate that the accomplishment of this protocol relies on the dual functionality of the photoexcited triplet nitroarenes, which serve as the oxygen atom source and enable the single-electron transfer (SET) process with CF 3 SO 2 Na.
Topics & Concepts
ChemistryCatalysisEnvironmentally friendlyTrifluoromethylCombinatorial chemistryPhotocatalysisPhotochemistryElectron transferMolecular oxygenOrganic chemistryEcologyBiologyAlkylFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsRadical Photochemical Reactions