ArticleNature chemistry2020
Rapid functionalization of multiple C-H bonds in unprotected alicyclic amines.
Article in Nature chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed, 103 citations in OpenAlex.
- Deciphering competing reaction pathways in the α-C-H functionalization of unprotected alicyclic aminesOrganic chemistry frontiers : an international journal of organic chemistry · 2026Article
- B(COrganic letters · 2026Article
- Chemical Tagging ofJournal of the American Chemical Society · 2025Article
- Regiodivergent α- and β-Functionalization of SaturatedJournal of the American Chemical Society · 2025Article
- Cyclic Imine-BFSynlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Diversified ring expansion of saturated cyclic amines enabled by azlactone insertion.Nature chemistry · 2024Article
- Selective C-N Bond Cleavage in Unstrained Pyrrolidines Enabled by Lewis Acid and Photoredox Catalysis.Journal of the American Chemical Society · 2024Article
- Photocatalytic Decarboxylative Alkylation of Cyclic Imine-BFJournal of the American Chemical Society · 2024Article
- Regioselective α-Phosphonylation of Unprotected Alicyclic Amines.Organic letters · 2024Article
- Alicyclic-Amine-Derived Imine-BFAngewandte Chemie (International ed. in English) · 2024Article
- Synthesis of dienes from pyrrolidines using skeletal modification.Nature communications · 2023Article
- High-throughput synthesis provides data for predicting molecular properties and reaction success.Science advances · 2023Article
- 1,2-Redox Transpositions of Tertiary Amides.Journal of the American Chemical Society · 2023Article
- Palladium-Catalyzed Arylation of Endocyclic 1-Azaallyl Anions: Concise Synthesis of Unprotected Enantioenriched cis-2,3-Diarylpiperidines.Angewandte Chemie (International ed. in English) · 2023Article
- Article
- Transannular Functionalization of Multiple C(spOrganometallics · 2023Article
- Vicinal stereocentersChemical science · 2023Article
- Regioselective α-Cyanation of Unprotected Alicyclic Amines.Organic letters · 2022Article
- Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.Organic letters · 2022Article
- α,α'-C-H Bond Difunctionalization of Unprotected Alicyclic Amines.Organic letters · 2021Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The synthesis of valuable bioactive alicyclic amines containing variable substituents in multiple ring positions typically relies on multistep synthetic sequences that frequently require the introduction and subsequent removal of undesirable protecting groups. Although a vast number of studies have aimed to simplify access to such materials through the C-H bond functionalization of feedstock alicyclic amines, the simultaneous introduction of more than one substituent to unprotected amines has never been accomplished. Here we report an advance in C-H bond functionalization methodology that enables the introduction of up to three substituents in a single operation. Lithiated amines are first exposed to a ketone oxidant, generating transient imines that are subsequently converted to endocyclic 1-azaallyl anions, which can be processed further to furnish β-substituted, α,β-disubstituted, or α,β,α'-trisubstituted amines. This study highlights the unique utility of in situ-generated endocyclic 1-azaallyl anions, elusive intermediates in synthetic chemistry.
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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.