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Figure 3. Experimental conditions and the cyclic voltammogram of a 5 mL solution of 1 (10 mM) Catalysts 2019, 9, 413 5 of 12 before (black line) and after (blue line) controlled potential electrolysis under an inert atmosphere with a glassy carbon electrode (top) and silver electrode (bottom). Scan rate: 0.5 V s−1. Taking into account the cyclic voltammetry and controlled potential electrolysis experiments, Taking into account the cyclic voltammetry and controlled potential electrolysis experiments, it it is possible to conclude that 1 followed the Electron transfer, Chemical reaction, Electron transfer is possible to conclude that 1 followed the Electron transfer, Chemical reaction, Electron transfer (ECE) mechanism. Hence, in a first electrochemical step (E) the radical anion, 1−, was generated. (ECE) mechanism. Hence, in a first electrochemical step (E) the radical anion, 1 −, was generated. A A chemical reaction (C) coupled to this first electron transfer led to a benzonitrile radical and an chemical reaction (C) coupled to this first electron transfer led to a benzonitrile radical and an iodide iodide anion through a C–I bond cleavage reaction. Finally, the radical was reduced to an anion at the anion through a C–I bond cleavage reaction. Finally, the radical was reduced to an anion at the electrode surface (E), which later protonated by reacting with the solvent (Scheme 2). Note that the electrode surface (E), which later protonated by reacting with the solvent (Scheme 2). Note that the electrochemical generation of benzonitrile anion, which acts as a nucleophile leading to benzonitrile, electrochemical generation of benzonitrile anion, which acts as a nucleophile leading to benzonitrile, opened the door to incorporate CO2 via nucleophile-electrophile reaction through the electrochemical opened the door to incorporate CO2 via nucleophile-electrophile reaction through the electrochemical reduction of 1. reduction of 1. Scheme 2. ECE mechanism proposal for the electrochemical reduction of 1 for both media. 2.2. ElectrocShcehmeimcael 2R. eEdCuEctmioencohfa4n-isIomdopbreonpzoosnailtfroilretuhne deelercatrCocahrebmonicDaliorexdiduect(iCoOn o)f A1 ftomrobsoptherme edia. Electrochemical Reduction Mechanism of 4-Iodobenzonitrile on Carbon and Silver Cathodes 4-Iodobenzonitrile (1) showed a different electrochemical behavior at GC and silver cathodes in DMF under a CO2 atmosphere. When GC was used, two reduction peaks were observed at −1.83 V and −2.35 V, the first one corresponding to the electrochemical reduction of 1, and the second one to the electrochemical reduction of benzonitrile (Figure 4a). It is worth noting that in the presence of CO2 there was an increase in the peak current value of this second reduction peak and a loss of reversibility, which indicated that the benzonitrile was acting as an organic mediator for the reduction of CO2 through a homogeneous indirect catalytic process [41,42]. In the corresponding anodic counter scan, a new oxidation peak was observed at 0.45 V, which corresponded to the oxidation of the oxalate anion generated in the CO2 reduction process under a saturated CO2 atmosphere [43] (Scheme 3). Note that the peaks at higher oxidation potential values corresponded to the oxidation of iodide and triiodide, respectively. Due to the low oxidation potential value of silver, it was not possible to record any anodic counter scan so as to detect the nature of the anionic products formed. 2PDF Image | Electrocatalytic Processes for the Valorization of CO2
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