ArticleNature chemistry2025
Modular alkyl growth in amines via the selective insertion of alkynes into C-C bonds.
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 6 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
6 citing papers in PubMed.
- Article
- Skeletal Reorganization of Cycloalkylamines Into Angular Azatetracyclic Scaffolds.Angewandte Chemie (International ed. in English) · 2026Article
- Successive Ring Expansion Strategies for the Synthesis of Macrocycles and Medium-Sized Rings.Chemical reviews · 2026Article
- B(COrganic letters · 2026Article
- Chemodivergent Coupling of 1,3-Enynes with Anilines to Access Dihydropyrrole Skeleton under Palladium Catalysis.Nature communications · 2026Article
- Chemical Tagging ofJournal of the American Chemical Society · 2025Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
The site-specific modification of amines has been a highly sought-after objective in organic synthesis. Despite the rapid advancement of carbon-hydrogen (C-H) bond functionalization methods, effective strategies for carbon-carbon (C-C) bond functionalization of amines remain elusive. Here we report a borane-catalysed method for the selective insertion of alkynes into alkyl C-C bonds of amines, resulting in the ring expansion of cyclic amines and chain elongation of acyclic amines. This approach begins with the cleavage of C-H bonds in amines, then transitioning to C-C bond functionalization upon reaction with alkynes. This method is effective with amines lacking an activating or leaving group and is suitable for late-stage functionalization of pharmaceuticals through C-C bond modification. Furthermore, by coupling this reaction with hydrolysis and hydrogenation steps, successive alkyne insertions are achieved, enabling modular and iterative alkyl growth of amines.
Identifiers
40506572What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.