ArticleNature chemistry2025
Carbon-to-nitrogen atom swap enables direct access to benzimidazoles from drug-like indoles.
Article in Nature chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Oxetane-to-azetidine skeletal editing.Nature chemistry · 2026Article
- Embracing triplet nitrenes for C-to-N replacement of complex bicyclic (hetero)aryl azides.Science (New York, N.Y.) · 2026Article
- Sulfur-to-Metal Single-Atom Editing of a Thiourea Self-Assembled Monolayer into an Adatom-Bound N-Heterocyclic Carbene Monolayer on Coinage Metal Surfaces.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Direct Access to the SimplestJACS Au · 2026Article
- Formal nitrogen-to-carbon replacement in isoindolines to form indenesChemical science · 2026Article
- Direct access to 2-imidazolines from unactivated alkenes.Chemical science · 2026Article
- Pyridine C─N Transposition via Cycloaddition-Cycloreversion.Angewandte Chemie (International ed. in English) · 2026Article
- Nitrogen atom insertion and related skeletal editing strategies in aromatic heterocycles for drug discovery (2015-2025).Molecular diversity · 2026Review
- Shape-Conserving Atom Replacements.Chemical reviews · 2026Review
- Photoinduced H-Bonding EDA complex-enabled skeletal editing of furans to pyridazines.Nature communications · 2026Article
- Enantioselective Pyrazole Alkylation via Iridium and Squaramide Catalyzed N-H Insertion.Journal of the American Chemical Society · 2026Article
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- Article
- Iodonitrene-Mediated Nitrogen Transfer to Alkenes for the Direct Synthesis of NH-Aziridines.Journal of the American Chemical Society · 2025Article
- Phototransposition of Indazoles to Benzimidazoles: Tautomer-Dependent Reactivity, Wavelength Dependence, and Continuous Flow Studies.Angewandte Chemie (International ed. in English) · 2025Article
- Chemodivergent C-to-N atom swap from benzofurans to benzisoxazoles and benzoxazoles.Chemical science · 2025Article
- Article
- Unifying principles for the design and evaluation of natural product-inspired compound collections.Chemical science · 2025Review
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The ability to selectively edit organic molecules at the atomic level has the potential to streamline lead discovery and optimization in the pharmaceutical and agrochemical industry. While numerous atom insertion and deletion reactions have recently been reported, examples of single atom swaps remain scarce due to the challenge of orchestrating the selective cleavage and formation of multiple chemical bonds around the same atom. Here we report a method for the carbon-to-nitrogen atom swap in N-alkyl indoles, allowing the direct conversion of indoles to the corresponding benzimidazoles. The reaction leverages the innate reactivity of the indole scaffold to engage in an initial oxidative cleavage step, followed by oxidative amidation, Hofmann-type rearrangement and cyclization. This complex sequence of steps is mediated by the simple combination of commercially available phenyliodine(III) diacetate and ammonium carbamate as the nitrogen atom source. The reaction tolerates a wide range of functional groups, which is demonstrated by the interconversion of 15 drug-like molecules, implying its immediate applicability across a wide range of discovery programmes.
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