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.
Authors
- Javier García‐Cárceles (ORCID: https://orcid.org/0000-0003-4614-9639)
- John F. Bower (ORCID: https://orcid.org/0000-0002-7551-8221)
- Karim A. Bahou (ORCID: https://orcid.org/0000-0002-8302-5283)
- Peter R. Ledwith
- Madelene L. Cooney
- J.S. Thomson
Institutions
- University of Liverpool (GB)
- University of Bristol (GB)
Publication Details
- Journal
- Angewandte Chemie
- Published
- 2024-08-26
- DOI
- https://doi.org/10.1002/ange.202411555
- Citations
- 1
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Fundación Alfonso Martín Escudero
- University of Bristol
- Engineering and Physical Sciences Research Council
- European Research Council