We present a Pd-IPent-catalyzed ring-opening defluorinative annulation reaction of gem-difluorocyclopropanes with enamides, which provides a convenient and efficient strategy for the synthesis of multisubstituted N-H pyrrole derivatives. This transformation selectively cleaves the C1-C3 bond, two C-F bonds, and the C-N bond in a one-pot procedure. Additionally, this protocol allows for the modification of several bioactive molecules.