3-Trifluoromethyl Pyrrole Synthesis Based on β-CF<sub>3</sub>-1,3-Enynamides
Zongxiang Yu, Jintong Li, Yuxuan Cao, Tingwei Dong, Yuanjing Xiao
Abstract
A new metal-free method for the rapid, productive, and scalable preparation of 3-trifluoromethyl pyrroles has been developed. It is based on the electrophilic nature of the double bond of β-CF 3 -1,3-enynamides due to the electron-withdrawing characteristics of the trifluoromethyl groups and the strong nucleophilic nature of alkyl primary amines. Evidence for the highly regioselective 1,4-hydroamination was observed after the isolation and characterization of the allenamide intermediate.
Topics & Concepts
TrifluoromethylHydroaminationRegioselectivityNucleophileChemistryElectrophilePyrroleAlkylCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsSynthesis and Reactions of Organic Compounds