Transition-Metal-Free C–H Trifluoromethylthiolation of <i>N,N</i>-Disubstituted Enaminones To Access CF<sub>3</sub>S-Functionalized Enaminones and Their Application in the Synthesis of CF<sub>3</sub>S-Heteroaryls
Jinbiao Ying, Tao Zhou, Yunyun Liu, Liyun Zhou, Jie‐Ping Wan
Abstract
The α-C–H trifluoromethylthiolation of N,N -disubstituted enaminones has been achieved with simple and cheap CF 3 SO 2 Na as the CF 3 S source. The reactions were run at mild temperature (0 °C to rt) using POCl 3 as the only reducing reagent. The work represents the first example on the synthesis of α-trifluoromethylthio enaminones via direct C–H functionalization. In addition, the resulting CF 3 S-functionalized enaminones have been proven as useful building blocks in the synthesis of various CF 3 S-functionalized heteroaromatic compounds by simple annulation reactions.
Topics & Concepts
ChemistryReagentAnnulationCombinatorial chemistrySurface modificationTransition metalOrganic chemistryCatalysisPhysical chemistryFluorine in Organic ChemistryInorganic Fluorides and Related Compounds