Related Experiment Video
Updated: Jan 22, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Iodine-catalysed transfer hydrogenation of a carbon-carbon σ-bond with water
Wu Yang1, Ching Tat To1, Kin Shing Chan1
1Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, People's Republic of China. ksc@cuhk.edu.hk.
Abstract:
Iodine catalysed the transfer hydrogenation of a benzylic C-C σ-bond in [2.2]paracyclophane with water to yield 4,4'-dimethylbibenzyl. The C-C σ-bond was first cleaved by homolytic substitution with iodine radicals to produce a 4,4'-diiodomethylbibenzyl intermediate. The benzylic C-I bonds in this intermediate were subsequently reduced by HI, generated in situ from the disproportionation of I2 with H2O, to achieve transfer hydrogenation and regenerate I2.
More Related Videos
Related Concept Videos
Hydrogen Bonds
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
Hydrogen Bonds
Carbon Skeletons
The Carbon Cycle
Carbonation Shrinkage
The concrete's permeability is slightly reduced as calcium carbonate produced during the reaction fills its pores. Furthermore, its strength is slightly enhanced as the water released during the reaction...
Ionic Bonding and Electron Transfer

