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A Simple Protocol for the C−N Cross‐Coupling of Aryl Chlorides with Amines Applying Ni/NHC Catalysis Научная публикация

Журнал Chemcatchem
ISSN: 1867-3899 , E-ISSN: 1867-3880
Вых. Данные Год: 2023, Том: 15, Номер: 13, Номер статьи : e202300466, Страниц : DOI: 10.1002/cctc.202300466
Авторы Khazipov Oleg 1 , Pyatachenko Anastasia 1 , Chernyshev Victor 2 , Ananikov Valentine P. 2,3
Организации
1 Uzno-Rossijskij gosudarstvennyj politehniceskij universitet NPI imeni M I Platova, Chemistry, RUSSIAN FEDERATION
2 Platov South-Russian State Polytechnic University (NPI), Prosveschenya 132, Novocherkassk, 346428 Russia
3 Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, 119991 Russia

Реферат: 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.
Библиографическая ссылка: 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
Идентификаторы БД:
Web of science: WOS:001003491400001
Scopus: 2-s2.0-85161463659
OpenAlex: W4376874290
Цитирование в БД:
БД Цитирований
OpenAlex 3
Scopus 2
Web of science 2
Альметрики: