Palladium-Catalyzed Dearomative Fluoroallylation of Pyrroles with <i>gem</i>-Difluorinated Cyclopropanes
Long Gu, Feimeng Duan, Jiafeng Ye, Zhipeng Zhao, Zhengquan Su, Wei Li, Yue Zhang, Zhaodong Li
Abstract
We herein report the development of a novel Pd-catalyzed dearomative functionalization of pyrroles with gem -difluorinated cyclopropanes ( gem -F 2 CPs). This dearomative/ring-opening strategy streamlines the diversity-oriented synthesis (DOS) of α-quaternary 2-fluoroallylic 2 H -pyrroles with a broad scope and excellent functional group tolerance, which enables the efficient late-stage transformation of complex bioactive molecule-derived gem -F 2 CPs. Derivation of the resulting fluoroallylic 2 H -pyrroles to different synthetically useful fluoroallylic 2 H -pyrrole motifs demonstrated the synthetic value of this methodology.
Topics & Concepts
ChemistryPalladiumCatalysisCombinatorial chemistryMedicinal chemistryOrganic chemistryStereochemistryFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Characterization of Pyrroles