Recent Progress in Electrochemical Late-Stage C(sp²)–H Functionalization

Dedication

Dedicated to Prof. Dr. Paul Knochel on the occasion of his 70^th birthday.

Abstract

Late-stage C–H functionalization has gained rapid development as a key approach in modern synthetic methodology, particularly for the transformation of structurally complex molecules. This strategy has reformed retrosynthetic logic and improved synthetic efficiency. C(sp²)–H functionalization, as a pivotal part in late-stage functionalization, has significantly promoted the development of medicinal chemistry. However, the latter often employ transition metal catalysts, in combination with stoichiometric amounts of chemical oxidants, which severely compromise their sustainability, functional group tolerance, and their extension to industrial applications. In sharp contrast, electrochemical late-stage C(sp²)–H functionalization has emerged as a more sustainable and environmentally friendly alternative, where electrons are used as clean redox agents. Therefore, this approach obviates the need for toxic chemical oxidants, enabling reactions to be operative under milder conditions, allowing for a wide scope of redox transformations. In this review, we highlight the recent progress in the electrochemical late-stage functionalization of C(sp²)–H bonds from 2019 to 2025, with particular focus on the formation of C(sp²)–C, C(sp²)–O, C(sp²)–N, and C(sp²)–P bonds.

Keywords

Electrochemistry - Late-stage functionalization - C–H activation - Transition-metal catalysis - Bioactive molecules

1

Introduction

Organic electrosynthesis has gained recognition as a robust and environmentally friendly strategy for achieving molecular transformations, serving as a sustainable alternative to conventional synthetic methods.[1] [2] [3] By harnessing electrons as traceless redox agents, electrochemistry techniques avoid the use of stoichiometric amounts of chemical oxidants or reductants. This allows reactions to proceed under milder conditions, enhances their compatibility with sensitive functional groups, as well as broadens the accessible redox potentials window for complex synthetic applications.[4] Therefore, electrochemical methodologies are increasingly employed in scalable and selective bond-forming strategies, establishing themselves as attractive and powerful tools in contemporary organic chemistry.

Late-stage C–H functionalization allows the direct introduction of new functional groups into otherwise unreactive C–H bonds.[5] This not only improves atom economy but also simplifies synthetic routes by significantly reducing the number of necessary synthetic steps required. Consequently, such strategies are highly attractive for the late-stage diversification of structurally complex molecules, including active pharmaceutical ingredients and natural products.[6] However, traditional late-stage C(sp²)–H functionalization often relies on expensive transition-metal catalysts as well as stoichiometric amounts of chemical oxidants, such as silver or copper salts.[7] The latter significantly hinders the development of environmentally benign and economically feasible approaches.

This review summarizes recent progress in electrochemical late-stage C(sp²)–H functionalization, focusing on direct, regio-, and chemo-selective transformation of C–H bonds to construct C(sp²)–C, C(sp²)–O, C(sp²)–N, and C(sp²)–P bonds in structurally diverse and biologically relevant molecules ([Fig. 1]). Moreover, particular attention is given to its application in late-stage functionalization of natural products, drugs, peptides, and other architecturally complex compounds, highlighting its significant potential in advancing sustainable synthetic chemistry.

Fig. 1 Overview of electrochemical late-stage C(sp²)–H functionalization.

2

Electrochemical Late-Stage C(sp²)–C Formation

Methylation represents a well-established example of late-stage functionalization, which was widely employed to enhance the pharmacological profiles of bioactive compounds by improving metabolic stability, lipophilicity, and molecular recognition, an effect often referred to as the “magic methyl effect”.[8] Anodic C(sp²)–H methylation enabled by transition metal catalysis offers a viable strategy that avoids the use of stoichiometric strong oxidants.[9] [10] In 2022, Ackermann and coworkers reported a rhodium-catalyzed electrooxidative C(sp²)–H methylation of N-heteroarene-containing substrates, utilizing potassium methyltrifluoroborate as the methyl source ([Scheme 1]).[11] This method accomplished the site-selective methylation of complex scaffolds such as purines, diazepam, and amino acid derivatives. A proposed catalytic cycle commences with carboxylate-assisted C–H activation to form the rhodacycle intermediate Int-1. Transmetalation with potassium methyltrifluoroborate then yields the more readily oxidizable species Int-2. This intermediate undergoes oxidation-induced reductive elimination to afford the desired product and a rhodium(II) species, which is subsequently oxidized anodically to regenerate the active rhodium(III) catalyst. Concurrently, proton reduction occurs at the cathode, releasing H₂. Subsequently, Guo expanded the substrate scope using a similar strategy to encompass natural products such as estrone and nucleoside analogues.[12]

Scheme 1 Electrochemical rhodium-catalyzed C(sp²)–H methylation.

Trifluoromethyl plays a pivotal role in medicinal chemistry due to its strong electron-withdrawing properties and influence on metabolic stability, lipophilicity, and bioavailability.[13] In 2014, Baran and coworkers reported the electrochemical C(sp²)–H trifluoromethylation of bio-relevant heterocycles using zinc trifluoromethanesulfinate [Zn(CF₃SO₂)₂] as the CF₃ radical precursor under anodic conditions ([Scheme 2]).[14] This strategy was later adapted to enable difluoromethylation by employing Zn(CF₂HSO₂)₂ as the reagent, although the overall efficiency of the difluoromethylation was comparatively lower.

Scheme 2 Electrochemical late-stage trifluoromethylation and difluoromethylation.

In 2020, Ackermann and coworkers reported a straightforward photoelectrochemical strategy for the C(sp²)–H trifluoromethylation of arenes utilizing sodium trifluoromethanesulfinate as the CF₃ source ([Scheme 3]).[15] This method exhibited a broad substrate scope and demonstrated excellent functional group tolerance. Moreover, it proved effective for the late-stage trifluoromethylation of complex natural products, including pentoxifylline, doxofylline, theobromine, methyl estrone, and tryptophan. Notably, Wu and coworkers developed a photoelectrochemical method that employs trifluoroacetic acid as a trifluoromethylating reagent for efficient trifluoromethylation of diverse (hetero)arenes.[16]

Scheme 3 Photoelectrochemical C(sp²)–H trifluoromethylation.

In 2025, Ackermann devised a strategy for C─H fluoroalkylation through photoelectrochemical iron(III) catalysis ([Scheme 4]).[17] This strategy accommodates a wide range of fluoroalkyl radical types, utilizing fluorinated carboxylic acids as practical and easily accessible precursors. Notably, the method allows for chemo- and site-selective late-stage modification of structurally intricate biomolecules, including unprotected nucleosides.

Scheme 4 C(sp²)–H fluoroalkylation by photoelectrochemical Iron(III) catalysis.

In 2019, the Xu group developed a transition metal-free photoelectrochemical strategy for the late-stage C(sp²)–H alkylation of bioactive heteroarenes using organotrifluoroborates as alkyl radical precursors ([Scheme 5]).[18] This method was successfully applied to the selective functionalization of diverse natural products and pharmaceutical agents, including purine, voriconazole, camptothecin, fasudil, and quinine. Inspired by this strategy, the same group further extended this methodology to alkyl carboxylic acids[19] and alkanes[20] as radical precursors for the late-stage modification of drug-like heteroarenes. In parallel, other groups, including Chen,[21] Wang,[22] Lambert,[23] and Lei,[24] have also explored diverse photoelectrochemical C–H functionalization strategies, thereby enriching the repertoire of late-stage derivatization approaches in complex molecules. In 2025, Xu elaborated a photoelectrocatalytic C–H hexafluoroisopropylation of indoles and tryptophan-containing peptides, employing hexafluoro-2-propanol (HFIP) as the fluoroalkylating agent.[25]

Scheme 5 C(sp²)–H alkylation of bioactive heteroarenes.

In 2020, Shi and Xie reported an electrochemical iridium-catalyzed directed C(sp²)–H alkynylation employing terminal alkynes as coupling partners ([Scheme 6]).[26] This electrocatalytic transformation proceeded in an undivided cell without the need for external oxidants and delivered excellent yields. Notably, its applicability to the late-stage functionalization of bioactive compounds such as estrone and purine derivatives showcases its potential utility in medicinal chemistry.

Scheme 6 Electrochemical C(sp²)–H alkynylation.

Electrochemical C–H annulation methods have increasingly attracted attention due to their ability to bypass the use of sacrificial oxidants such as Cu(OAc)₂ and AgOAc, thereby minimizing by-product formation and improving atom economy.[27] In 2021, the Ackermann group developed a rhodium-catalyzed electrooxidative formyl C–H activation strategy for the annulation of 2-hydroxybenzaldehydes with alkynes ([Scheme 7]).[28] This method enabled the site-selective functionalization of tyrosine derivatives, allowing for the electrochemical labeling of fluorescent amino acids and peptides. Notably, a broad range of peptide substrates, including ones bearing oxidation-sensitive functional groups, were efficiently modified.

Scheme 7 Rhodaelectro-catalyzed peptide late-stage labeling.

3

Late-Stage C(sp²)–O Bond Formation

Hydroxylation of arene C(sp²)–H bonds is a valuable transformation in medicinal chemistry, as it can significantly enhance the aqueous solubility of drug candidates. However, achieving controlled electrochemical hydroxylation of arenes remains challenging, primarily due to the susceptibility of phenol intermediates to overoxidation.[29] In this context, trifluoroacetic acid-mediated approaches for the generation of aryl trifluoroacetates were developed to moderate the oxidation reaction. Nevertheless, their applicability is often limited to specific arene substrates.[30] To overcome these limitations, the Xu group introduced a continuous-flow electrochemical microreactor setup that enabled the selective hydroxylation of a broad range of arenes under metal-free and oxidant-free conditions ([Scheme 8]).[31] This mild and scalable approach effectively suppresses overoxidation and was successfully applied to the late-stage modification of natural products and drug derivatives.

Scheme 8 Electrochemical C(sp²)–H hydroxylation.

In 2022, the Ackermann group reported a ruthenium-electrocatalyzed late-stage C(sp²)–H acyloxylation of tyrosine-containing peptides ([Scheme 9]).[32] This method exhibited broad substrate scope, showing excellent compatibility with diverse carboxylic acids and enabling efficient acyloxylation of di-, tri-, and tetrapeptides without inducing epimerization of stereochemically sensitive residues.

Scheme 9 Electrochemical C(sp²)–H acyloxylation of tyrosine-containing peptides.

4

Late-Stage C(sp²)–N Bond Formation

Electrooxidative C–H/N–H cross-coupling has emerged as an efficient strategy for the direct incorporation of nitrogen-based functional groups into aromatic frameworks. In 2019, the Lei group reported an intermolecular electrochemical cross-coupling between sulfonyl imines and arenes, proceeding via a nitrogen-centered radical addition mechanism ([Scheme 10]).[33] This strategy demonstrated broad applicability, enabling the late-stage functionalization of structurally diverse molecules, including flavonoids, caffeine, and fenofibrate.

Scheme 10 Electrochemical late-stage aminations.

In 2024, the Malapit group reported on an electrochemical highly selective aromatic C–H amination ([Scheme 11]).[34] This approach involved the generation of highly electrophilic dicationic nitrogen radicals through cathodic reduction, which facilitates aromatic C–H functionalization while dictating the regioselectivity. The reaction exhibited broad substrate scope including diverse drug molecules such as fenofibrate, flurbiprofen, bifonazole, and celecoxib derivatives.

Scheme 11 Electrochemical late-stage aminations with selectfluor.

In 2019, Lei reported an electrooxidative tyrosine bioconjugation method employing phenothiazine derivatives ([Scheme 12]),[35] which exhibited both high efficiency and high selectivity, facilitating the modification of key biomolecules as well as fluorescent labeling of peptides. A plausible mechanism involves single-electron oxidation of phenothiazine at the anode, yielding a nitrogen-centered radical. This radical subsequently undergoes radical addition at the ortho-position of the phenol, which, after anodic oxidation followed by deprotonation, delivers the desired products.

Scheme 12 Electrochemical peptide and protein modification on tyrosine.

In 2025, the Xu group reported a continuous-flow electrochemical C(sp²)–H amination technique that facilitates scalable and efficient synthesis of valuable primary aromatic amines from diverse arene substrates ([Scheme 13]).[36] This methodology features a broad substrate scope that includes a wide range of electron-deficient and electron-rich arenes, as well as heterocycles, demonstrating excellent functional group tolerance and high regioselectivity. The application of late-stage electrochemical amination was demonstrated on a range of complex molecules, including clofene, triclosan, isoxepac, procymidone, pyriproxyfen, and flurbiprofen.

Scheme 13 Late-stage aminations by continuous flow electrochemistry.

5

Late-Stage C(sp²)–P Bond Formation

Given the extensive applications of organophosphorus compounds in medicinal chemistry, the development of efficient late-stage phosphorylation strategies is of high significance. In 2019, Xu and coworkers reported a rhodium-catalyzed late-stage aromatic C(sp²)–H phosphorylation reaction utilizing inexpensive and readily available phosphine oxides ([Scheme 14]).[37] This approach demonstrated applicability in the late-stage modification of various bioactive molecules, such as diazepam and purine derivatives. This strategy presented high functional group tolerance, broad applicability, and facile scalability in the absence of stoichiometric chemical oxidants. A plausible catalytic cycle is depicted in [Scheme 14]. Initially, carboxylate-assisted C–H activation yields the rhodacycle intermediate Int-1. After ligand exchange with 30, it gives rise to the more easily oxidized complex Int-2. Oxidation-induced reductive elimination then delivers product 31 along with either a rhodium(III) or rhodium(II) species, dictated by the oxidation level of Int-3. If a rhodium(II) complex is produced, it is reoxidized at the anode to regenerate the rhodium(III) catalyst. Concurrently, H₂ evolution occurs via proton reduction at the cathode.

Scheme 14 Electrochemical rhodium-catalyzed C(sp²)–H phosphorylation.

In 2021, Xu and coworkers further developed an electrochemical aromatic C(sp²)–H phosphorylation employing triethyl phosphite in a continuous-flow electrochemical cell ([Scheme 15]).[38] The latter exhibited broad compatibility with both electron-rich and electron-deficient arenes without chemical oxidants and transition-metal catalysts, facilitating selective late-stage functionalization of a variety of bioactive molecules and natural products. A plausible mechanism is depicted in [Scheme 15]. Initially, trialkyl phosphite 31 undergoes anodic oxidation to form a phosphorus-centered radical cation. This intermediate reacts with the arene substrate, resulting in a distally substituted radical cation. Subsequent anodic oxidation and deprotonation yields a phosphonium intermediate, which then undergoes dealkylation to furnish the final phosphonate product.

Scheme 15 Electrochemical late-stage C(sp²)–H phosphorylation in continuous flow.

In 2025, Ackermann described an efficient ruthenium-electrocatalyzed site-selective ortho-C–H phosphorylation of arenes ([Scheme 16]),[39] driven by the electrochemical hydrogen evolution reaction, thereby eliminating the need for stoichiometric chemical oxidants and minimizing redox-waste by-products. Notably, this strategy also enabled an unprecedented ruthenaelectro-catalyzed para-C–H phosphorylation with exceptional site selectivity. This electrocatalytic approach exhibited broad substrate compatibility, thus enabling late-stage phosphorylation of several pharmaceutically relevant molecules such as diazepam, oxaprozin, and purine riboside.

Scheme 16 Electrochemical Ru-catalyzed late-stage C(sp²)–H phosphorylation.

6

Conclusion

This review highlights recent advances in electrochemical late-stage C(sp²)–H functionalization, a rapidly evolving powerful strategy for the late-stage diversification of bioactive molecules. By replacing stoichiometric chemical oxidants with green electrons as traceless redox agents, electrochemical methods significantly improve atom economy and environmental compatibility, while overcoming challenges associated with harsh reaction conditions and limited substrate scope. Significant progress has been achieved in the transformation of C(sp²)–H bonds into C(sp²)–C, C(sp²)–O, C(sp²)–N, and C(sp²)–P bonds, thereby broadening the synthetic applicability of this strategy and enabling the direct modification of pharmaceuticals, natural products, and other structurally complex molecules. These developments showcase the great potential of electrochemical synthesis in lead compound optimization and drug discovery, offering new directions for the development of green and efficient synthetic paradigms. However, electrochemical approaches for late-stage C–H functionalization remain relatively underdeveloped compared to those involving simple substrates. Numerous factors in complex molecular architectures contribute to this disparity, including the presence of multiple sensitive functional groups, the site-selectivity challenges arising from various types of C–H bonds, poor solubility, and competing side reactions such as overoxidation. Managing these challenges requires meticulous reaction condition optimization. Both metal-catalyzed and metal-free strategies face distinct hurdles in electrochemical late-stage C(sp²)–H functionalization. Metal-catalyzed strategies need to address potential issues of metal residue contamination, a critical concern in pharmaceutical synthesis, as well as the costs associated with some catalysts. Metal-free methodologies often require high oxidation potentials, which often prevents a broad functional group tolerance and precise site-selectivity without the direct influence of a metal catalyst. Further efforts are required to deepen mechanistic understanding, facilitate the scalability of electrochemical platforms, and achieve site-selective modifications on increasingly complex bioactive molecules. Addressing these challenges will be crucial for enabling the practical implementation and industrial application of electrochemical C–H functionalization.

Yanjun Li

Yanjun Li was born in Hubei, China, in 1992. He received his BSc degree from Hubei University in 2015 and his PhD under the supervision of Prof. Lei Gong at the Xiamen University in 2020. After one year as a research assistant at the same the university, he joined the research group of Prof. Lutz Ackermann as a postdoctoral researcher at the University of Göttingen. His research focuses on the development of new strategies for asymmetric catalysis and C–H functionalization.

Jinbin Zhu

Jinbin Zhu received his PhD degree from East China University of Science and Technology in 2020 under the supervision of Prof. Wenjun Tang and Prof. Wei-Ping Deng. In the same year, he joined the Gannan Normal University as a lecturer. Between 2023 and 2025, he joined Prof. Lutz Ackermann’s research group at the University of Göttingen as a postdoctoral researcher. His current research interest focuses on C–H activation.

Jiandong Liu

Jiandong Liu received his Bachelor’s degree from the Qufu Normal University in 2014. He then pursued his Master’s studies at the Shanghai Institute of Technology and Shanghai University under the supervision of Prof. Xinghua Zhang and Prof. Hegui Gong. In 2020, he completed his PhD at the Shanghai University with Prof. Hegui Gong. From 2021 to 2024, he carried out postdoctoral research at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, under the supervision of Prof. Shu-Li You. Currently, he is a postdoctoral researcher in the group of Prof. Lutz Ackermann at the University of Göttingen. His research focuses on metal-catalyzed cross-coupling reactions, allylic substitution, electrochemistry, and sugar chemistry.

Lutz Ackermann

Lutz Ackermann studied chemistry at the University Kiel (Germany), and performed his PhD with Prof. Alois Fürstner at the Max-Planck-Institut für Kohlenforschung (Mülheim/Ruhr, 2001). After a postdoctoral stay at UC Berkeley with Prof. Robert G. Bergman, he initiated his independent research career in 2003 at the Ludwig Maximilians-University München. In 2007, he became Full Professor (W3) at the Georg-August-University, Göttingen. His recent awards and distinctions include an AstraZeneca Excellence in Chemistry Award (2011), an ERC Consolidator Grant (2012), a Gottfried-Wilhelm-Leibniz-Preis (2017), an ERC Advanced Grant (2021), and an ERC Proof of Concept Grant (2025). The development and application of novel concepts for sustainable catalysis constitute his major current research interests, with a topical focus on electrocatalysis and bond activation.

Contributorsʼ Statement

Y.L.: Conceptualization, Writing – original draft, Writing – review & editing. J.Z.: Conceptualization, Writing – original draft, Writing – review & editing. J.L.: Conceptualization, Writing – original draft, Writing – review & editing. L.A.: Conceptualization, Project administration, Resources, Supervision, Writing – original draft, Writing – review & editing.

Conflict of Interest

The authors declare that they have no conflict of interest.

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Publication History

Received: 08 August 2025

Accepted after revision: 23 September 2025

Article published online:
20 November 2025