Rapid Assembly of Diversely Functionalized Spiroindenes by a Three-Component Palladium-Catalyzed C-H Amination/Phenol Dearomatization Domino Reaction

A novel palladium-catalyzed three-component reaction of phenol-derived biaryls with N-benzoyloxyamines and norbornadiene (NBD) has been developed for the assembly of highly functionalized spiroindenes. This domino process was realized through NBD-assisted C-H amination and phenol dearomatization by forming one C-N bond and two C-C bonds in a single step. Preliminary studies indicated that asymmetric control of this transformation was feasible with chiral ligands. Moreover, the potential synthetic utility of this methodology was highlighted by a series of further transformations.