Related Experiment Video
Updated: Aug 8, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Tandem one-Pot palladium-catalyzed reductive and oxidative coupling of benzene and chlorobenzene
Mukhopadhyay1, Rothenberg, Gitis
1Casali Institute of Applied Chemistry, Hebrew University of Jerusalem, 91904, Israel.
Abstract:
The in situ combination of oxidative coupling of benzene to biphenyl and reductive coupling of chlorobenzene (also to biphenyl) using palladium catalysts (Pd(2+)/Pd(0)) is described. In each cycle, the reductive process regenerates the catalyst for the oxidative process and vice versa. Kinetic investigations show that the reaction rate depends on [C(6)H(6)], [C(6)H(6)Cl], and catalyst loading, with E(a)() = 13 kcal mol(-)(1). The reduced palladium catalyst undergoes deactivation through aggregation and precipitation, but it is observed that during this deactivation process the Pd(0) becomes an active catalyst for the reductive coupling of chlorobenzene. Accordingly, while Pd(0)/C particles are inactive, Pd(0) colloids do catalyze the tandem reaction. Conversion is increased in the presence of a phase-transfer catalyst, presumably due to stabilization of the active Pd(0) clusters. The two halves of the catalytic cycle are examined in the light of previous research, regarding analogous oxidative and reductive coupling reactions, using stoichiometric amounts of PdCl(2) and Pd(0), respectively. The roles of homogeneous PdCl(2) and Pd(0) clusters are discussed.
More Related Videos
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Related Concept Videos
Preparation and Reactions of Sulfides
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Hydrolysis of Chlorobenzene to Phenol: Dow Process
Reactions at the Benzylic Position: Halogenation
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction