Palladium-catalyzed difluorocarbene transfer enables access to enantioenriched chiral spirooxindoles.

ABSTRACT: We disclose herein an unprecedented Pd-catalyzed difluorocarbene transfer reaction, which assembles a series of structurally interesting chiral spiro ketones with generally over 90% ee. Commercially available BrCF₂CO₂K serves as the difluorocarbene precursor, which is harnessed as a user-friendly and safe carbonyl source in this transformation. Preliminary mechanistic studies exclude the formation of free CO in the reaction process, and importantly, we also find that BrCF₂CO₂K outcompete gaseous CO and several common CO surrogates in this asymmetric process. The reaction mechanism, including the in-situ progressive release of the difluorocarbene, the rapid migratory insertion of ArPd(II) = CF₂ species, and subsequent defluorination hyd

SUBMITTER: Nie Z 

PROVIDER: S-EPMC11445564 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature