Proceedings of MATSUS23 & Sustainable Technology Forum València (STECH23) (MATSUS23)
DOI: https://doi.org/10.29363/nanoge.matsus.2023.302
Publication date: 22nd December 2022
The construction of carbonyl compounds via carbonylation reaction using a safe CO source remains a long-standing challenge to synthetic chemists.[1] In this work, we explored the electrosynthetic approach using CO2 as a CO surrogate in the carbonylation of benzyl chlorides, utilizing a combination of two earth-abundant metal catalysts. As proof of concept, the protocols allow the synthesis of symmetric ketones from good to excellent yields in an undivided cell with non-sacrificial electrodes. The mechanistic studies suggested a synergistic effect between the two metal complexes. Based on the mechanistic studies, we propose the coupling of the electrocatalytic CO formed from CO2 reduction with the benzyl chlorides activated by the Ni-catalyzed. Our approach that has proven more challenging is the use of an undivided cell to perform tandem CO2 reduction to CO, followed by CO utilization in carbonylation reactions. While this approach has the potential to offer several benefits such as simple experimental setups, straightforward synthetic protocols, direct utilization of the CO formed, decrease of the employed toxic CO, and facilitation of the formation of labeled compounds. This is complex due to the need to balance all required catalytic cycles. Few methods used CO2 as a CO source because of its inertness but also due to its inherent reactivity that delivers preferably carboxylation products. In this line, Skrydstrup, Daasbjerg and co-workers developed a set of classical Pd-catalyzed carbonylation reactions using the CO evolved from the electrochemical CO2 reduction in a two-compartment setup.[2] Before that, Perichon and co-workers reported a stepwise electrochemical/chemical method for the stoichiometric synthesis of ketones.[3]
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