NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates

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Abstract: Umpolung N‐heterocyclic carbene (NHC) catalysis of non‐aldehyde substrates offers new pathways for C−C bond formation, but has proven challenging to develop in terms of viable substrate classes. Here, we demonstrate that pyridinium ions can undergo NHC addition and subsequent intramolecular C−C bond formation through a deoxy‐Breslow intermediate. The alkylation demonstrates, for the first time, that deoxy‐Breslow intermediates are viable for catalytic umpolung of areniums.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates ; day:18 ; month:02 ; year:2022 ; extent:1
Angewandte Chemie ; (18.02.2022) (gesamt 1)

Creator: Wu, Terence
Tatton, Matthew R.
Greaney, Michael F.

DOI: 10.1002/ange.202117524

URN: urn:nbn:de:101:1-2022021814125700470909

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:30 AM CEST

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Wu, Terence
Tatton, Matthew R.
Greaney, Michael F.

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NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates

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Other Objects (12)

NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy‐Breslow Intermediates

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Key intermediates in NHC-catalyzed reactions of activated esters and novel NHC ligands for gold catalysis

N-heterocyclic carbenes : aromatic Breslow intermediates, synthesis of novel electron-deficient NHC catalysts and NHC catalysis

Asymmetric C–H Alkylation of Fluoroarenes with Alkenes via Nickel/NHC Catalysis

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Transition‐Metal‐Free Alkylation of N‐Heterocycles with Nitriles via Heteroarylphosphonium Intermediates

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Synthese und Eigenschaften makrozyklischer 4-Pyridinium-Redox-Systeme [Pyridinium-Redox-Systeme]

Pyridinium-Crosslinks : Knochenstoffwechsel und Peritonealdialyse

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Key intermediates in NHC-catalyzed reactions of activated esters and novel NHC ligands for gold catalysis

N-heterocyclic carbenes : aromatic Breslow intermediates, synthesis of novel electron-deficient NHC catalysts and NHC catalysis

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NHC-catalyzed annulations via homoenolate and α,β - unsaturated acylazolium intermediates

Transition‐Metal‐Free Alkylation of N‐Heterocycles with Nitriles via Heteroarylphosphonium Intermediates

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NHC Umpolung of enals key intermediates and novel catalysts for selective synthesis

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Key intermediates in NHC-catalyzed reactions of activated esters and novel NHC ligands for gold catalysis

N-heterocyclic carbenes : aromatic Breslow intermediates, synthesis of novel electron-deficient NHC catalysts and NHC catalysis

Asymmetric C–H Alkylation of Fluoroarenes with Alkenes via Nickel/NHC Catalysis

NHC-catalyzed annulations via homoenolate and α,β - unsaturated acylazolium intermediates

Transition‐Metal‐Free Alkylation of N‐Heterocycles with Nitriles via Heteroarylphosphonium Intermediates

Transition‐Metal‐Free Alkylation of N‐Heterocycles with Nitriles via Heteroarylphosphonium Intermediates

NHC Umpolung of enals key intermediates and novel catalysts for selective synthesis

Metal Halide Exchange in Benzylborane NHC‐Adducts: The Effect of Backbone Alkylation in the N ‐Heterocyclic Carbene

Synthese und Eigenschaften makrozyklischer 4-Pyridinium-Redox-Systeme [Pyridinium-Redox-Systeme]

Pyridinium-Crosslinks : Knochenstoffwechsel und Peritonealdialyse

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