ArticleNature communications2021
Organophotocatalytic selective deuterodehalogenation of aryl or alkyl chlorides.
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 26 papers.
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Who cites it
26 citing papers in PubMed.
- Solvent-controlled Rh-catalysed hydrodehalogenation and construction of phenanthridinone skeleton from a common precursor in one-step sequence and the antitumor activity of its derivatives.Journal of enzyme inhibition and medicinal chemistry · 2026Article
- Electrochemical functionalization of pyridines.Chemical science · 2026Review
- Photocatalytic Cross-Coupling of Phenols and Heteroaryl Halides With Machine Learning-Guided Reaction Prediction.Angewandte Chemie (International ed. in English) · 2026Article
- Electricity-driven site-selective deuteration of pharmaceuticals.Chemical science · 2026Article
- Asymmetric synthesis of chiral boronic esters featuring nonadjacent axial and flexible, acyclic central chirality.Science advances · 2025Article
- Deuteration of Six-Membered N-Heteroarenes: Chemistry and Applications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- Scalable reductive deuteration of (Hetero)Aryl chlorides with DNature communications · 2025Article
- Mechanochemical Dehalogenative Deuteration of Alkyl Halides Through Piezoelectric Catalysis Initiated by a Single-Electron Oxidation Strategy.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Late-Stage Serine Modification Enables Noncanonical Peptide Synthesis.Journal of the American Chemical Society · 2025Article
- Pd-catalyzed deuteration of aryl halides with deuterium oxide.Nature communications · 2025Article
- Catalytic Reductive Homocoupling of Benzyl Chlorides Enabled by Zirconocene and Photoredox Catalysis.Precision chemistry · 2025Article
- Hydro- and deutero-deamination of primary amines using O-diphenylphosphinylhydroxylamine.Nature communications · 2024Article
- Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes.Nature communications · 2024Article
- Radical Replacement Process for Ligated Boryl Radical-Mediated Activation of Unactivated Alkyl Chlorides for C(spJournal of the American Chemical Society · 2024Article
- Electroreductive deuteroarylation of alkenes enabled by an organo-mediator.Chemical science · 2024Article
- Metallaphotoredox deuteroalkylation utilizing thianthrenium salts.Nature communications · 2024Article
- Electrochemical C-H deuteration of pyridine derivatives with DNature communications · 2024Article
- Photocatalytic Dehalogenative Deuteration of Halides over a Robust Metal-Organic Framework.Angewandte Chemie (International ed. in English) · 2023Article
- Chlorine Atom Transfer of Unactivated Alkyl Chlorides Enabled by Zirconocene and Photoredox Catalysis.Precision chemistry · 2023Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Development of practical deuteration reactions is highly valuable for organic synthesis, analytic chemistry and pharmaceutic chemistry. Deuterodehalogenation of organic chlorides tends to be an attractive strategy but remains a challenging task. We here develop a photocatalytic system consisting of an aryl-amine photocatalyst and a disulfide co-catalyst in the presence of sodium formate as an electron and hydrogen donor. Accordingly, many aryl chlorides, alkyl chlorides, and other halides are converted to deuterated products at room temperature in air (>90 examples, up to 99% D-incorporation). The mechanistic studies reveal that the aryl amine serves as reducing photoredox catalyst to initiate cleavage of the C-Cl bond, at the same time as energy transfer catalyst to induce homolysis of the disulfide for consequent deuterium transfer process. This economic and environmentally-friendly method can be used for site-selective D-labeling of a number of bioactive molecules and direct H/D exchange of some drug molecules.
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