Palladium-catalyzed C–C bond cleavage of N-cyclopropyl acylhydrazones

Abstract

Despite their utility as directing groups, the C–C bond cleavage of cyclopropanes utilizing hydrazones has not been explored. Herein, Pd-catalyzed C–C bond cleavage reaction of N-cyclopropyl acylhydrazones, followed by cycloisomerization to yield pyrazoles, has been developed. The protocol enables the synthesis of various α-pyrazole carbonyl compounds, which have a potential of biological activity. Control experiments and DFT calculations suggest that β-carbon elimination of a stable 6-membered chelate palladium complex occurs, generating a conjugated azine as a reaction intermediate for the following cycloisomerization.