Related Experiment Video
Updated: Sep 28, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Increasing the oxidation power of TCNQ by coordination of B(C6F5)3
Paul Anton Albrecht1, Susanne Margot Rupf1, Malte Sellin1,2
1Freie Universität Berlin, Institute of Chemistry and Biochemistry, Fabeckstr. 34-36, 14195 Berlin, Germany. moritz.malischewski@fu-berlin.de.
Abstract:
The oxidation power of the cyanocarbon TCNQ (tetracyano-quinodimethane) can be significantly increased to approximately E = +0.9 V vs. Cp2Fe by coordination of up to four equivalents of the strong fluorinated Lewis acid B(C6F5)3, resulting in a highly reactive but easy-to-use oxidation system. Thianthrene and tris(4-bromophenyl)amine were oxidized to the corresponding radical cations. Dianionic [TCNQ·4 B(C6F5)3]2- was formed upon reduction with two equivalents of ferrocene or decamethylcobaltocene. [TCNQ·4 B(C6F5)3]- and [TCNQ·4 B(C6F5)3]2- are rare cases of redox-active weakly-coordinating anions.
Related Concept Videos
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...
Radical Reactivity: Concentration Effects
Coordination Compounds and Nomenclature
Coordination Number and Geometry
Valence Bond Theory
Hydroboration-Oxidation of Alkenes

![[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)