A Simple Protocol for the C−N Cross‐Coupling of Aryl Chlorides with Amines Applying Ni/NHC Catalysis Full article
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Chemcatchem
ISSN: 1867-3899 , E-ISSN: 1867-3880 |
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| Output data | Year: 2023, Volume: 15, Number: 13, Article number : e202300466, Pages count : DOI: 10.1002/cctc.202300466 | ||||||
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Abstract:
An efficient protocol for the C−N cross-coupling of aryl chlorides with (hetero)aryl- and alkyl amines under nickel catalysis has been developed. The main advantage of the protocol is the use of a self-activated Ni/NHC catalytic system generated in situ from readily available bench-stable air-tolerant precursors: NiCl2Py2, IPr ⋅ HCl, and sodium tert-butoxide. A mass spectrometry mechanistic study of the reaction system revealed the dynamics of competitive processes of Ni/NHC active species formation and degradation involving NHC reductive elimination reactions and tert-butoxide base. Optimization of the NiCl2Py2/IPr ⋅ HCl/tBuONa ratio and the reaction temperature allowed efficient catalysis to be achieved. The developed simple protocol represents an alternative for methods relying on the use of air-sensitive and unstable Ni(cod)2 or expensive well-defined Ni/NHC precatalysts.
Cite:
Khazipov O.
, Pyatachenko A.
, Chernyshev V.
, Ananikov V.P.
A Simple Protocol for the C−N Cross‐Coupling of Aryl Chlorides with Amines Applying Ni/NHC Catalysis
Chemcatchem. 2023. V.15. N13. e202300466 . DOI: 10.1002/cctc.202300466 WOS Scopus OpenAlex
A Simple Protocol for the C−N Cross‐Coupling of Aryl Chlorides with Amines Applying Ni/NHC Catalysis
Chemcatchem. 2023. V.15. N13. e202300466 . DOI: 10.1002/cctc.202300466 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:001003491400001 |
| Scopus: | 2-s2.0-85161463659 |
| OpenAlex: | W4376874290 |