ArticleChemical science2020
N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 172 citations in OpenAlex.
- Asymmetric radical NHC organocatalysis-enabled highly enantioselective acylation of inert C(spScience advances · 2026Article
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- NHC-Mediated Radical Acylation Catalyzed by Thiamine- and Flavin-Dependent Enzymes.Journal of the American Chemical Society · 2025Article
- Local reaction condition optimization via machine learning.Journal of molecular modeling · 2025Review
- Synthesis of Secondary Boronates via Deaminative Cross-Coupling of Alkyl Nitroso Carbamates and Boronic Acids.Angewandte Chemie (International ed. in English) · 2024Article
- Harnessing the potential of acyl triazoles in bifunctional cobalt-catalyzed radical cross-coupling reactions.Nature communications · 2024Article
- Photoinduced cerium-catalyzed C-H acylation of unactivated alkanes.Chemical science · 2023Article
- Recent advances in combining photo- and N-heterocyclic carbene catalysis.Chemical science · 2023Review
- Ketones from aldehydes via alkyl C(spNature communications · 2023Article
- On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis.ACS organic & inorganic Au · 2023Article
- Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis.Nature communications · 2023Article
- A Brief Introduction to Chemical Reaction Optimization.Chemical reviews · 2023Review
- Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes.Nature communications · 2022Article
- Solid-Phase Peptide Modification via Deaminative Photochemical CspChemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones.Nature communications · 2022Article
- Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.Topics in current chemistry (Cham) · 2022Review
- Enantioselective functionalization at the C4 position of pyridinium salts through NHC catalysis.Nature communications · 2022Article
- Single-electron Carbene Catalysis in Redox Processes.Trends in chemistry · 2022Article
- NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones.Chemical science · 2022Article
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Authors and funding
4 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
By employing an N-heterocyclic carbene (NHC) catalyst, we developed a versatile catalytic system that enables deaminative cross-coupling reactions of aldehydes with redox-active pyridinium salts. Katritzky pyridinium salts behave as single-electron oxidants capable of generating alkyl radicals enabled by the redox properties of the enolate form of Breslow intermediates. The resultant alkyl radical undergoes efficient recombination with the NHC-bound aldehyde-derived carbonyl carbon radical for the formation of a C-C bond. The mild and transition metal-free reaction conditions tolerate a broad range of functional groups, and its utility has been further demonstrated by the modification of a series of peptide feedstocks and application to the three-component dicarbofunctionalization of olefins.
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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.