A Strategy for the Formal C−N Cross‐Coupling of Tertiary Amines
Abstract: We report a strategy for the formal C−N cross‐coupling of tertiary amines via the in situ generation and displacement of N‐acyl ammonium species. Specifically, treatment of diverse tertiary amines with TFAA or chloroformates in the presence of NaI leads to the efficient generation of alkyl iodides, which can be engaged directly in Ni‐catalyzed cross‐couplings. The protocol is applicable to acyclic and cyclic systems, including highly hindered variants. Applications to the late‐stage modification of complex heterocycles are presented.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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A Strategy for the Formal C−N Cross‐Coupling of Tertiary Amines ; day:22 ; month:10 ; year:2024 ; extent:7
Angewandte Chemie / International edition. International edition ; (22.10.2024) (gesamt 7)
- Creator
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Ledwith, Peter R.
Cooney, Madelene L.
Bahou, Karim A.
García‐Cárceles, Javier
Thomson, Joshua
Bower, John F.
- DOI
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10.1002/anie.202411555
- URN
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urn:nbn:de:101:1-2410231444133.798556684157
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:33 AM CEST
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Associated
- Ledwith, Peter R.
- Cooney, Madelene L.
- Bahou, Karim A.
- García‐Cárceles, Javier
- Thomson, Joshua
- Bower, John F.
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Direct Cross-Coupling of Phenols with Amines Using Palladium on Carbon
Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines
Oxidative cross-coupling reactions
Applied cross-coupling reactions
Catalytic Conjunctive Cross-Coupling
Photoelectrochemical Ni-catalyzed cross-coupling of aryl bromides with amine at ultra-low potential
UVA LED Light Promoted Cross‐Coupling of Tertiary α ‐Silylamines with 1‐Iodoalkynes
The Hiyama–Denmark Cross-Coupling
Polycyclic Aromatics via Cross-Coupling
The Liebeskind–Srogl Cross-Coupling
Cobalt-catalyzed cross-coupling reactions
A Strategy for the Formal C−N Cross‐Coupling of Tertiary Amines
Direct Cross-Coupling of Phenols with Amines Using Palladium on Carbon
Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines
Oxidative cross-coupling reactions
Applied cross-coupling reactions
Catalytic Conjunctive Cross-Coupling
Photoelectrochemical Ni-catalyzed cross-coupling of aryl bromides with amine at ultra-low potential
UVA LED Light Promoted Cross‐Coupling of Tertiary α ‐Silylamines with 1‐Iodoalkynes
The Hiyama–Denmark Cross-Coupling
Polycyclic Aromatics via Cross-Coupling
The Liebeskind–Srogl Cross-Coupling