Related Experiment Video
Updated: Feb 8, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Oxidation of Hindered Allylic C-H Bonds with Applications to the Functionalization of Complex Molecules
Zachary C Litman1, Ankit Sharma1, John F Hartwig1
1Department of Chemistry, University of California, Berkeley, California 94720, United States.
Abstract:
We report the palladium-catalyzed oxidation of hindered alkenes to form linear allylic esters. The combination of palladium(II) benzoate, 4,5-diazafluoren-9-one, and benzoquinone catalyzes the mild oxidation of terminal alkenes with tert-butyl benzoyl peroxide as an oxidant in the presence of diverse functional groups. Selective oxidation of terminal alkenes in the presence of trisubstituted and disubstituted alkenes has been achieved, and the ability to conduct the reaction on a gram scale has been demonstrated. The mild conditions and high tolerance for auxiliary functionality make this method suitable for the synthesis and derivatization of complex molecules.
Related Concept Videos
Radical Oxidation of Allylic and Benzylic Alcohols
Metal-Ligand Bonds
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
Oxidation and Reduction of Organic Molecules
The removal of an electron from a molecule, results in a...
Bond Energies and Bond Lengths
Peptide Bonds
Oxidation Numbers

