Palladium-CatalyzedDearomative Fluoroallylation ofPyrroles with <i>gem</i>-Difluorinated Cyclopropanes

We herein report the development of a novel Pd-catalyzed dearomative functionalization of pyrroles with <i>gem</i>-difluorinated cyclopropanes (<i>gem</i>-F₂CPs). This dearomative/ring-opening strategy streamlines the diversity-oriented synthesis (DOS) of α-quaternary 2-fluoroallylic 2<i>H</i>-pyrroles with a broad scope and excellent functional group tolerance, which enables the efficient late-stage transformation of complex bioactive molecule-derived <i>gem</i>-F₂CPs. Derivation of the resulting fluoroallylic 2<i>H</i>-pyrroles to different synthetically useful fluoroallylic 2<i>H</i>-pyrrole motifs demonstrated the synthetic value of this methodology.