ArticleJournal of the American Chemical Society2020
Photoredox-Catalyzed Deaminative Alkylation via C-N Bond Activation of Primary Amines.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 113 citations in OpenAlex.
- Vicinal disubstitution of alkyl C-X synthons via alkene radical cation generation.Science (New York, N.Y.) · 2026Article
- Pyridinium Design for Deaminative Reactions of Sterically Encumbered Alkyl Amines.Organic letters · 2026Article
- Catalyst-Free Photoinduced Deaminative Functionalization of Amino Acids and Glutarimide Precursors.Journal of the American Chemical Society · 2026Article
- Palladium-Catalyzed Deaminative Cross-Coupling of Alkyl Nitroso Carbamates.ACS catalysis · 2026Article
- Article
- Deaminative Giese-type reaction.Nature chemistry · 2025Article
- Photocatalyzed C(spOrganic letters · 2025Article
- Accessing sulfonamides via formal SONature chemistry · 2025Article
- Catalytic diazene synthesis from sterically hindered amines for deaminative functionalization.Nature communications · 2025Article
- Modular Synthesis of Dehydroprolines by an Energy-Transfer Enabled Cloke-Wilson Rearrangement.Angewandte Chemie (International ed. in English) · 2025Article
- Visible-Light-Mediated Deaminative Alkylation of Primary Amines with Silacarboxylic Acids via Isonitrile Formation.Organic letters · 2025Article
- Low-energy photoredox catalysis.Nature reviews. Chemistry · 2025Review
- Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis.Science advances · 2024Article
- Synthesis of Secondary Boronates via Deaminative Cross-Coupling of Alkyl Nitroso Carbamates and Boronic Acids.Angewandte Chemie (International ed. in English) · 2024Article
- Engaging Alkenes in Metallaphotoredox: A Triple Catalytic, Radical Sorting Approach to Olefin-Alcohol Cross-Coupling.Journal of the American Chemical Society · 2024Article
- Photoredox-Catalyzed Generation of Tertiary Anions from Primary Amines via a Radical Polar Crossover.Angewandte Chemie (International ed. in English) · 2024Article
- Late-Stage Isotopic Exchange of Primary Amines.Journal of the American Chemical Society · 2023Article
- Harnessing Sulfur(VI) Fluoride Exchange Click Chemistry and Photocatalysis for Deaminative Benzylic Arylation.ACS catalysis · 2023Article
- Cross-Coupling of Amines via Photocatalytic Denitrogenation of In Situ Generated Diazenes.Journal of the American Chemical Society · 2023Article
- Direct Activation of the C(spJournal of the American Chemical Society · 2023Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Primary amines are often cheap, naturally occurring, and chemically diverse starting materials. For these reasons, deaminative functionalization of amines has emerged as an important area of research. Recent advances in C-N activation transform simple α-1° and α-2° amines into alkylating reagents via Katritzky pyridinium salts. We report a complementary method that activates sterically encumbered α-3° primary amines through visible light photoredox catalysis. By condensing α-3° primary amines with electron-rich aryl aldehyde, we enable an oxidation and deprotonation event, which generates a key imidoyl radical intermediate. A subsequent β-scission event liberates alkyl radicals for coupling with electron-deficient olefins for the generation of unnatural γ-quaternary amino acids and other valuable synthetic targets.
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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.