ArticleNature communications2021
Electrochemical C-H phosphorylation of arenes in continuous flow suitable for late-stage functionalization.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Article
- Review
- Electrochemical Oxidation of Aryl Boronic Acids via Fluoride Activation and Alternating Polarity Electrolysis for Aryl C-P Bond Formation.ChemElectroChem · 2025Article
- Recent advances in the electrochemical synthesis of organophosphorus compounds.Beilstein journal of organic chemistry · 2025Review
- Electrochemical-induced phosphorylation of arenols and tyrosine containing oligopeptides.iScience · 2024Article
- Electrochemical synthesis of peptide aldehydes via C‒N bond cleavage of cyclic amines.Nature communications · 2024Article
- Continuous flow synthesis enabling reaction discovery.Chemical science · 2024Review
- Recent Advances in the Application of P(III)-Nucleophiles to Create New P-C Bonds through Michaelis-Arbuzov-Type Rearrangement.Topics in current chemistry (Cham) · 2024Review
- Bulky, electron-rich, renewable: analogues of Beller's phosphine for cross-couplings.Catalysis science & technology · 2023Article
- Electrochemical Late-Stage Functionalization.Chemical reviews · 2023Review
- The crucial role of silver(I)-salts as additives in C-H activation reactions: overall analysis of their versatility and applicability.Chemical Society reviews · 2023Review
- Scalable electrosynthesis of commodity chemicals from biomass by suppressing non-Faradaic transformations.Nature communications · 2023Article
- Review
- One-pot H/D exchange and low-coordinated iron electrocatalyzed deuteration of nitriles in DNature communications · 2022Article
- Direct Electrooxidative Selenylation/Cyclization of Alkynes: Access to Functionalized Benzo[Molecules (Basel, Switzerland) · 2022Article
- Electrochemical aromatic C-H hydroxylation in continuous flow.Nature communications · 2022Article
- Electrochemically driven regioselective C-H phosphorylation of group 8 metallocenes.Nature communications · 2022Article
- Recent advances in electrochemical C-H phosphorylation.Frontiers in chemistry · 2022Review
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The development of efficient and sustainable methods for carbon-phosphorus bond formation is of great importance due to the wide application of organophosphorus compounds in chemistry, material sciences and biology. Previous C-H phosphorylation reactions under nonelectrochemical or electrochemical conditions require directing groups, transition metal catalysts, or chemical oxidants and suffer from limited scope. Herein we disclose a catalyst- and external oxidant-free, electrochemical C-H phosphorylation reaction of arenes in continuous flow for the synthesis of aryl phosphorus compounds. The C-P bond is formed through the reaction of arenes with anodically generated P-radical cations, a class of reactive intermediates remained unexplored for synthesis despite intensive studies of P-radicals. The high reactivity of the P-radical cations coupled with the mild conditions of the electrosynthesis ensures not only efficient reactions of arenes of diverse electronic properties but also selective late-stage functionalization of complex natural products and bioactive compounds. The synthetic utility of the electrochemical method is further demonstrated by the continuous production of 55.0 grams of one of the phosphonate products.
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