Diazotrifluoroethyl Radical: A CF<sub>3</sub>-Containing Building Block in [3 + 2] Cycloaddition
Wenwen Zhao, Yong-Chao Shao, Anni Wang, Jiali Huang, Chun‐Yang He, Bao‐Dong Cui, Nan‐Wei Wan, Yong‐Zheng Chen, Wen‐Yong Han
Abstract
We present herein a visible-light-induced [3 + 2] cycloaddition of a hypervalent iodine(III) reagent with α-ketoacids for the construction of 5-CF3-1,3,4-oxadiazoles that are of importance in medicinal chemistry. The reaction proceeds smoothly without a photocatalyst, metal, or additive under mild conditions. Different from the well-established trifluorodiazoethane (CF3CHN2), the diazotrifluoroethyl radical [CF3C(·)N2], a trifluoroethylcarbyne (CF3CĊ:) equivalent and an unusual CF3-containing building block, is involved in the present reaction system.
Topics & Concepts
Hypervalent moleculeCycloadditionChemistryReagentBlock (permutation group theory)IodineCombinatorial chemistryPhotocatalysisOrganic chemistryCatalysisMathematicsGeometryFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods