Palladium-Catalyzed Synthesis of Cyclopentane-Fused Benzocyclobutenes via Tandem Directed Carbopalladation/C−H Bond Functionalization

A new Pd-catalyzed reaction for the stereoselective synthesis of cyclopentane-fused benzocyclobutenes is described. These transformations
likely proceed via carbamate-directed carbopalladation followed by intramolecular C−H activation of an alkylpalladium intermediate. The
mechanistic relationship between these transformations and Pd-catalyzed reactions of γ-(n-Boc-amino)alkenes with aryl bromides that afford
pyrrolidines is discussed. Differences in reactivity between Pd-amino and Pd-amido complexes appear to play a key role in the outcome of
these transformations.