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Figure 10. Electrochemical defluorination deuteration of trifluoromethylbenzene.
Figure 9. Organoboron reagent-controlled selective deuterodefluorination.
Figure 8. Electrochemical dehalogenation deuteration of benzyl halide.
Figure 7. Electrochemical dehalogenation deuteration of unactivated alkyl halides.
Figure 6. Palladium-catalyzed electrochemical dehalogenation deuteration.
Figure 5. Electrochemical dehalogenation deuteration promoted by organic mediator.
Figure 4. Electrochemical dehalogenation deuteration with Cu NWAs as the cathode.
Figure 3. Electrochemical dehalogenation deuteration of aryl halides.
Figure 2. Early electrochemical dehalogenation deuteration efforts.
Figure 1. Electrochemical deuteration of halides.
Figure 10. Energy barriers of reductive eliminations from divalent Ni species (left) and trivalent Ni species (right) at PBE0-D3(BJ)/def2-TZVP-SMD(DMAc)//PBE0-D3(BJ)/def2-SVP-SMD(DMAc).
Figure 9. DFT calculations of the proposed mechanism at PBE0-D3(BJ)/def2-TZVP-SMD(DMAc)//PBE0-D3(BJ)/def2-SVP-SMD(DMAc).
Scheme 2. Proposed mechanism.
Figure 8. Cyclic voltammograms. Black line: NiBr₂·glyme (0.10 mmol), 5,5′-Me₂-bpy (0.15 mmol), TBAPF₆ (2.0 mmol), DMAc (10.0 mL). The scan rate was 100 mV/s. The solution resistance of 70.6 Ω was fully compensated. Red line: NiBr₂·glyme (0.10 mmol), 5,5′-Me₂-bpy (0.15 mmol), 4-CF₃-C₆H₄-Br (1.0 mmol), TBAPF6 (2.0 mmol), DMAc (10.0 mL). The scan rate was 100 mV/s. The solution resistance of 72.3 Ω was fully compensated.
Table 2. DFT calculations of relative reduction potentials (vs. SHE).
Scheme 1. Proposed formation mechanism of the self-coupling product 4.
Figure 7. Evaluations of aryl bromides bearing electron-donating groups. [a] Electrolyzed for 6 hours.
Figure 6. 3D structures of 4-Br-C₆H₄-Bpin 2e′ (up) and 4-Br-C₆H₄-B(Epin) 2e (down).
Figure 5. Evaluations of aryl bromides bearing electron-withdrawing groups. [a] Yields were determined by proton NMR using dibromomethane as an internal standard. [b] Electrolyzed for 6 hours.
Figure 4. Evaluations of α-cyanoacetates.

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