ArticleNature2014
Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles.
Article in Nature, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 103 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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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
103 citing papers in PubMed, 534 citations in OpenAlex.
- An alkyl-swap platform for late-stage modification of secondary N-methylamines.Nature chemistry · 2026Article
- B(COrganic letters · 2026Article
- Ligand-controlled regiodivergent and enantioselective C-H cyanation of secondary amines.Nature communications · 2026Article
- Conformation-driven C3-C(Nature catalysis · 2026Article
- Palladium-Catalyzed Regio- and Stereoselective C-H Alkynylation of Conjugated Dienols.JACS Au · 2025Article
- Pd(II)/PIDA-Enabled Migratory Triple Functionalization of Terminal Alkenes via a 1,2-C/Pd(IV) Dyotropic Rearrangement.Angewandte Chemie (International ed. in English) · 2025Article
- Dynamic behavior of molecular Pd-acetate trimers and dimers in heterogeneous vinyl acetate synthesis.Nature communications · 2025Article
- Chemical Tagging ofJournal of the American Chemical Society · 2025Article
- Synthesis and Application of Bioactive N-Functionalized Aziridines.Angewandte Chemie (International ed. in English) · 2025Review
- Catalytic aromatic C-H borylation via strained Si and Ge metallacycles.Nature communications · 2025Article
- Engineering Single Ni Sites on 3D Cage-like Cucurbit[n]uril Ligands for Efficient and Selective COAngewandte Chemie (International ed. in English) · 2025Article
- Article
- Light-driven C-H activation mediated by 2D transition metal dichalcogenides.Nature communications · 2024Article
- Palladium-catalysed methylene C(Nature synthesis · 2024Article
- Light-driven C-H activation mediated by 2D transition metal dichalcogenides.Research square · 2024Article
- Atroposelective hydroarylation of biaryl phosphines directed by phosphorus centres.Nature communications · 2023Article
- Coordinating activation strategy enables 1,2-alkylamidation of alkynes.Chemical science · 2023Article
- 1,2-Redox Transpositions of Tertiary Amides.Journal of the American Chemical Society · 2023Article
- Direct Cyclopalladation of Fluorinated Benzyl Amines by PdOrganometallics · 2023Article
- Tunably strained metallacycles enable modular differentiation of aza-arene C-H bonds.Nature communications · 2023Article
43 more citing papers are in PubMed but not listed here.
Corrections and comments
- Commented on by
- Erratum issued
Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The development of new chemical transformations based on catalytic functionalization of unactivated C-H bonds has the potential to simplify the synthesis of complex molecules dramatically. Transition metal catalysis has emerged as a powerful tool with which to convert these unreactive bonds into carbon-carbon and carbon-heteroatom bonds, but the selective transformation of aliphatic C-H bonds is still a challenge. The most successful approaches involve a 'directing group', which positions the metal catalyst near a particular C-H bond, so that the C-H functionalization step occurs via cyclometallation. Most directed aliphatic C-H activation processes proceed through a five-membered-ring cyclometallated intermediate. Considering the number of new reactions that have arisen from such intermediates, it seems likely that identification of distinct cyclometallation pathways would lead to the development of other useful chemical transformations. Here we report a palladium-catalysed C-H bond activation mode that proceeds through a four-membered-ring cyclopalladation pathway. The chemistry described here leads to the selective transformation of a methyl group that is adjacent to an unprotected secondary amine into a synthetically versatile nitrogen heterocycle. The scope of this previously unknown bond disconnection is highlighted through the development of C-H amination and carbonylation processes, leading to the synthesis of aziridines and β-lactams (respectively), and is suggestive of a generic C-H functionalization platform that could simplify the synthesis of aliphatic secondary amines, a class of small molecules that are particularly important features of many pharmaceutical agents.
Identifiers
What 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.