Related Experiment Video
Updated: Oct 10, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Chelation-assisted C-C bond activation of biphenylene by gold(i) halides
Hélène Beucher1, Johannes Schörgenhumer1, Estíbaliz Merino2,3
1Department of Chemistry, University of Zurich Winterthurerstrasse 190 Zurich CH 8057 Switzerland cristina.nevado@chem.uzh.ch.
Abstract:
A chelation-assisted oxidative addition of gold(i) into the C-C bond of biphenylene is reported here. The presence of a coordinating group (pyridine, phosphine) in the biphenylene unit enabled the use of readily available gold(i) halide precursors providing a new, straightforward entry towards cyclometalated (N^C^C)- and (P^C)-gold(iii) complexes. Our study, combining spectroscopic and crystallographic data with DFT calculations, showcases the importance of neighboring, weakly coordinating groups towards the successful activation of strained C-C bonds by gold.
More Related Videos
Related Concept Videos
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Complexation Equilibria: The Chelate Effect
Nucleophilic Aromatic Substitution: Elimination–Addition
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...

