Catalytic C-H bond functionalization with palladiumII: aerobic oxidative annulations of indoles
Eric M Ferreira1, Brian M Stoltz
1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Abstract:
A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C-H bond activation) followed by migratory insertion and beta-hydrogen elimination.
More Related Videos
Related Concept Videos
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry


