Scissoring Enaminone C═C Double Bond by Free Radical Process for the Synthesis of α-Trifluoromethyl Ketones with CF<sub>3</sub>SO<sub>2</sub>Na
Lu Gan, Qing Yu, Yunyun Liu, Jie‐Ping Wan
Abstract
The C═C double bond cleavage on tertiary enaminones, enabling the formation of a new C–CF3 bond, has been realized as a practical method for the synthesis of α-trifluoromethyl ketones with only the promotion of TBHP and ambient heating. Control experiments support that the reactions proceed via a featured free radical process. The deuterium labeling experiment employing D2O indicates that water participated in the product formation by donating the hydrogen atom for the newly generated α-C–H bond in the product.
Topics & Concepts
ChemistryTrifluoromethylDouble bondDeuteriumHydrogen atomBond cleavageMedicinal chemistryPhotochemistryOrganic chemistryCatalysisGroup (periodic table)AlkylPhysicsQuantum mechanicsFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Reactions of Organic Compounds