Electrochemical cascade of Knoevenagel condensation and reduction: a green strategy for intermolecular C(sp3)–C(sp3) bond formation

Electrochemical cascade of Knoevenagel condensation and reduction: a green strategy for intermolecular C(sp3)–C(sp3) bond formation Full article

Journal

Green Chemistry
ISSN: 1463-9262 , E-ISSN: 1463-9270

Output data

Year: 2026, DOI: 10.1039/D5GC06350G

Authors

Bityukov Oleg V. ¹ , Kirillov Andrey S. ¹ , Litvin Fedor A. ^1,2 , Vil' Vera A. ¹ , Terent'ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky pr., Moscow, Russian Federation
2	Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow, Russian Federation

An intermolecular C(sp3)–C(sp3) coupling of ketones with EWG-activated nitriles proceeding via a combination of Knoevenagel condensation of the starting substrates and cathodic reduction of an in situ-formed alkene has been discovered. NH4OAc was used as the base and the electrolyte, and a green solvent, aqueous EtOH, was applied as the medium. A high selectivity of C(sp3)–C(sp3) bond formation was achieved using available glassy carbon as the electrode material. The origin of an electrode's ability to control the reaction outcome was disclosed. A hydrogen adsorption free energy (ΔGH*) far from 0, low HER overpotential (high absolute value), and high OER overpotential were proposed factors that make glassy carbon ideal for the cascade of Knoevenagel condensation and reduction. The reaction proceeds under mild conditions, does not require hydride-based reductants, and provides moderate to good yields of the substituted nitriles.

Bityukov O.V. , Kirillov A.S. , Litvin F.A. , Vil' V.A. , Terent'ev A.O.
Electrochemical cascade of Knoevenagel condensation and reduction: a green strategy for intermolecular C(sp3)–C(sp3) bond formation
Green Chemistry. 2026. DOI: 10.1039/D5GC06350G

Submitted:	Nov 26, 2025
Accepted:	Feb 16, 2026
Published print:	Feb 18, 2026

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