Next Article in Journal
The Effect of Furanocoumarin Derivatives on Induction of Apoptosis and Multidrug Resistance in Human Leukemic Cells
Previous Article in Journal
Selective Adsorption-Based Separation of Flue Gas and Natural Gas in Zirconium Metal-Organic Frameworks Nanocrystals
Previous Article in Special Issue
High Sensitive Immunoelectrochemical Measurement of Lung Cancer Tumor Marker ProGRP Based on TiO2-Au Nanocomposite
Article Menu
Issue 9 (May-1) cover image

Export Article

Open AccessArticle

Evaluation of Transition Metal Catalysts in Electrochemically Induced Aromatic Phosphonation

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 420088 Kazan, Russia
Author to whom correspondence should be addressed.
Molecules 2019, 24(9), 1823;
Received: 22 April 2019 / Revised: 8 May 2019 / Accepted: 9 May 2019 / Published: 11 May 2019
(This article belongs to the Special Issue Organic Electrochemistry 2019)
PDF [1455 KB, uploaded 13 May 2019]
  |     |  


Voltammetry provides important information on the redox properties of catalysts (transition metal complexes of Ni, Co, Mn, etc.) and their activity in electrocatalytic reactions of aromatic C–H phosphonation in the presence of a phosphorus precursor, for example, dialkyl-H-phosphonate. Based on catalytic current growth of oxidation or reduction of the metal catalysts (CoII, MnII, NiII, MnII/NiII, MnII/CoII, and CoII/NiII), quantitative characteristics of the regeneration of catalysts were determined, for example, for MnII, NiII and MnII/NiII, CoII/NiII pairs. Calculations confirmed the previously made synthetic observations on the synergistic effect of certain metal ions in binary catalytic systems (MnIIbpy/NiIIbpy and NiIIbpy/CoIIbpy); for mixtures, the observed rate constants, or TOF, were 690 s−1 and 721 s−1, respectively, and product yields were higher for monometallic catalytic systems (up to 71% for bimetallic catalytic systems and ~30% for monometallic catalytic systems). In some cases, the appearance of pre-waves after adding H-phosphonates confirmed the preceding chemical reaction. It also confirmed the formation of metal phosphonates in the time scale of voltammetry, oxidizing or reducing at lower potentials than the original (RO)2P(O)H and metal complex, which could be used for fast diagnostics of metal ion and dialkyl-H-phosphonate interactions. Electrochemical transfer of an electron to (from) metal phosphonate generates a phosphonyl radical, which can then react with different arenes to give the products of aromatic C–H phosphonation. View Full-Text
Keywords: electrocatalysis; phosphonation; rate constants; cyclic voltammetry; C–H functionalization; metal complex electrocatalysis; phosphonation; rate constants; cyclic voltammetry; C–H functionalization; metal complex

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

Strekalova, S.; Khrizanforov, M.; Budnikova, Y. Evaluation of Transition Metal Catalysts in Electrochemically Induced Aromatic Phosphonation. Molecules 2019, 24, 1823.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top