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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Photochemically Mediated Toluene Oxidation through a Copper Complex.

Christian Noß^1,2, Richard Göttlich², Siegfried Schindler¹

¹Institute for Inorganic and Analytical Chemistry, Justus-Liebig-University Gießen, Heinrich-Buff-Ring 17, 35392, Gießen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|May 17, 2023

Summary

This study introduces a novel photochemical method for selectively oxidizing toluene to benzaldehyde using copper complexes and dioxygen. The process is catalytic, with the active copper species regenerated, and the tris(2-methylpyridyl)amine ligand shows the best performance.

Keywords:

benzaldehyde copper peroxido complexes photooxidation ruthenium bipyridine toluene oxidation

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Published on: June 14, 2018

Area of Science:

Photochemistry
Organometallic Chemistry
Green Chemistry

Background:

Benzaldehyde is a crucial industrial chemical.
Selective oxidation of toluene to benzaldehyde is challenging.
Photocatalysis offers a sustainable route for chemical synthesis.

Purpose of the Study:

To develop a selective photochemical oxidation method for toluene to benzaldehyde.
To investigate the role of copper(I) complexes and dioxygen in the catalytic cycle.
To identify optimal ligands for efficient toluene oxidation.

Main Methods:

Photochemical oxidation using copper(I) complexes and [Ru(bipy)3](PF6)2.
Employing dioxygen as the terminal oxidant.
Screening various ligands for copper complexation, including tris(2-methylpyridyl)amine (tmpa).

Main Results:

Selective formation of benzaldehyde from toluene was achieved.
A copper-oxygen adduct (peroxido complex) was identified as the active species.
The copper(II) product was photochemically reduced to the active copper(I) species, enabling a catalytic cycle.
The tris(2-methylpyridyl)amine (tmpa) ligand yielded the highest conversion rates.

Conclusions:

A sustainable and efficient photochemical method for benzaldehyde synthesis from toluene has been established.
Copper complexes, particularly with the tmpa ligand, are effective catalysts for this transformation.
The catalytic cycle involving photochemical reduction of the copper species offers a promising approach for industrial applications.