Research Progress in Metal-Free Electrochemical C—H Bond Activation for the Construction of C—N/C—O Bonds

doi:10.6023/cjoc202508020

Abstract

Electrochemical C—H bond activation has garnered significant attention due to its superior atom economy, abundant reaction sites, environmental friendliness, and the absence of substrate pre-functionalization requirements. C—N/C—O bonds, which are widely present in numerous natural products and pharmaceutical molecules, serve as crucial structural motifs in biological systems, making the development of efficient methodologies for their construction highly consequential. In recent years, with the growing emphasis on green chemistry principles, metal-free electrochemical C—H bond activation for C—N/C—O bond formation has emerged as a prominent research focus, owing to its advantages in avoiding metal residues, cost-effectiveness, and environmental compatibility. This field has witnessed the development of diverse strategies for constructing C—N/C—O bonds via electrochemical C—H activation. The key advancements in metal-free electrochemical C—H activation for C—N/C—O bond formation over the past five years are systematically reviewed, encompassing both direct C—N/C—O bond construction and non-metal-mediated approaches, with particular emphasis on elucidating the under- lying reaction mechanisms.

Key words: electrochemistry, C—H bond activation, green chemistry, metal-free, construction of C—N/C—O bonds

Cite this article

Hui Luo, Wenquan Wang, Yu He, Fuqiang Wang, Jinhui Yang. Research Progress in Metal-Free Electrochemical C—H Bond Activation for the Construction of C—N/C—O Bonds[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 697-724.

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Item compared	Transition metal-catalyzed C—H functionalization	Metal-free electrochemical C—H functionalization
Reaction mechanism	Using transition metals as catalysts, through elementary steps such as ligand exchange, oxidative addition, migration insertion, and reductive elimination, the activation and functionalization of C—H bonds are achieved.	Using electrons as clean oxidants or reductants, through electron transfer at the electrode surface, the substrate is transformed into active intermediates, thereby achieving the cleavage and functionalization of C—H bonds.
Reactive driving force	Chemical oxidants (such as Ag salts, Cu salts, peroxides, etc.) or reductants provide or consume electrons to complete the catalytic cycle.	Electric energy. By applying an external voltage or current, the redox potential of the reaction can be precisely controlled.
major advantage	(1) The method is mature and has a wide range of applications; (2) It offers strong selectivity and can be precisely controlled through ligand engineering; (3) The reaction conditions are relatively mild and facilitate large-scale production.	(1) Green and sustainable, reducing the use of metals and oxidants; (2) Economical in steps, without the need for pre-functionalization steps; (3) Unique reactivity, facilitating the generation of highly reactive free radical species; (4) High safety, capable of avoiding some dangerous chemical oxidants.
Main challenges and limitations	(1) The cost of metals is high and they may be toxic; (2) Metal residues affect the purity of the products, especially in the pharmaceutical industry; (3) They rely on chemical reagents for oxidation, generating chemical waste.	(1) Selective control (especially regional and stereoscopic selectivity) is a major challenge; (2) Reaction scaling is difficult due to limitations imposed by electrode area and mass transfer efficiency; (3) Special equipment (electrolytic cells, power supplies) is required; (4) Requirements exist for the conductivity of the substrate and solvent.
Catalyst and cost	(1) Expensive transition metal catalysts (such as Pd, Rh, Ir) are required; (2) It may involve the design and synthesis of complex ligands; (3) There is a problem of metal residue, which is not friendly to drug synthesis.	(1) No need for transition metal catalysts, and the cost is relatively low; (2) It may use inexpensive media (such as salts, acids, and bases) to facilitate conductivity; (3) No metal residues, especially suitable for the fields of medicine and materials.
Reaction selecti- vity	Regional selectivity: Usually precisely controlled through the spatial/electronic effects of directing groups or ligands, as well as catalysts. Stereoselectivity: High enantioselectivity can be achie- ved through chiral ligands.	Regional selectivity: It can be regulated by substrate structure (such as inherent electronic effects at the site), electrode potential, and medium, but precise activation of the distal C—H bond poses greater challenges. Stereoselectivity: It is relatively difficult to control and is currently a research difficulty.
Sustainability and “Green Chemis- try”	Using stoichiometric oxidants results in poorer atom economy. (1) Toxic or expensive metals may be used; (2) The process has high economic efficiency, but the environmental footprint is relatively large.	The atomic economy is high, and electrons act as “clean reagents”. (1) It is more in line with the principles of green chemistry (reducing waste and using renewable sources); (2) It can be combined with renewable energy sources (solar energy, wind energy).

Item compared	Transition metal-catalyzed C—H functionalization	Metal-free electrochemical C—H functionalization
Reaction mechanism	Using transition metals as catalysts, through elementary steps such as ligand exchange, oxidative addition, migration insertion, and reductive elimination, the activation and functionalization of C—H bonds are achieved.	Using electrons as clean oxidants or reductants, through electron transfer at the electrode surface, the substrate is transformed into active intermediates, thereby achieving the cleavage and functionalization of C—H bonds.
Reactive driving force	Chemical oxidants (such as Ag salts, Cu salts, peroxides, etc.) or reductants provide or consume electrons to complete the catalytic cycle.	Electric energy. By applying an external voltage or current, the redox potential of the reaction can be precisely controlled.
major advantage	(1) The method is mature and has a wide range of applications; (2) It offers strong selectivity and can be precisely controlled through ligand engineering; (3) The reaction conditions are relatively mild and facilitate large-scale production.	(1) Green and sustainable, reducing the use of metals and oxidants; (2) Economical in steps, without the need for pre-functionalization steps; (3) Unique reactivity, facilitating the generation of highly reactive free radical species; (4) High safety, capable of avoiding some dangerous chemical oxidants.
Main challenges and limitations	(1) The cost of metals is high and they may be toxic; (2) Metal residues affect the purity of the products, especially in the pharmaceutical industry; (3) They rely on chemical reagents for oxidation, generating chemical waste.	(1) Selective control (especially regional and stereoscopic selectivity) is a major challenge; (2) Reaction scaling is difficult due to limitations imposed by electrode area and mass transfer efficiency; (3) Special equipment (electrolytic cells, power supplies) is required; (4) Requirements exist for the conductivity of the substrate and solvent.
Catalyst and cost	(1) Expensive transition metal catalysts (such as Pd, Rh, Ir) are required; (2) It may involve the design and synthesis of complex ligands; (3) There is a problem of metal residue, which is not friendly to drug synthesis.	(1) No need for transition metal catalysts, and the cost is relatively low; (2) It may use inexpensive media (such as salts, acids, and bases) to facilitate conductivity; (3) No metal residues, especially suitable for the fields of medicine and materials.
Reaction selecti- vity	Regional selectivity: Usually precisely controlled through the spatial/electronic effects of directing groups or ligands, as well as catalysts. Stereoselectivity: High enantioselectivity can be achie- ved through chiral ligands.	Regional selectivity: It can be regulated by substrate structure (such as inherent electronic effects at the site), electrode potential, and medium, but precise activation of the distal C—H bond poses greater challenges. Stereoselectivity: It is relatively difficult to control and is currently a research difficulty.
Sustainability and “Green Chemis- try”	Using stoichiometric oxidants results in poorer atom economy. (1) Toxic or expensive metals may be used; (2) The process has high economic efficiency, but the environmental footprint is relatively large.	The atomic economy is high, and electrons act as “clean reagents”. (1) It is more in line with the principles of green chemistry (reducing waste and using renewable sources); (2) It can be combined with renewable energy sources (solar energy, wind energy).

无金属电化学C—H键活化构建C—N/C—O键的研究进展