Palladium-catalyzed synthesis of cyclopentane-fused benzocyclobutenes via tandem directed carbopalladation/C-H bond functionalization.

ABSTRACT: 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 gamma-(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.

SUBMITTER: Bertrand MB 

PROVIDER: S-EPMC2528069 | biostudies-literature | 2007 Aug

REPOSITORIES: biostudies-literature