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Ni/NHC catalysis in C–H functionalization using air-tolerant nickelocene and sodium formate for in situ catalyst generationстатья Исследовательская статья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 17 августа 2021 г.
- Авторы: Khazipov Oleg V., Shepelenko Konstantin E., Pasyukov Dmitry V., Chesnokov Vasilii V., Soliev Safarmurod B., Chernyshev Victor M., Ananikov Valentine P.
- Журнал: Organic Chemistry Frontiers
- Том: 8
- Номер: 11
- Год издания: 2021
- Первая страница: 2515
- Последняя страница: 2524
- DOI: 10.1039/d1qo00309g
- Аннотация: C–H functionalization in the area of fine organic synthesis is dominated by noble metal catalysts, which represent the most expensive and least sustainable options. Sustainable C–H functionalization may involve Ni catalysts. However, Ni(0) complexes are unstable under regular conditions and are more difficult to obtain as compared to Pd(0) or Rh(I). In the present study, a facile method for Ni0/NHC-catalyzed C–H alkylation and alkenylation of heteroarenes with alkenes and internal alkynes is presented. This method relies on the in situ generation of Ni0/NHC complexes from air-tolerant bench-stable precursors, Ni(Cp)2, NHC·HCl salts and sodium formate. The optimized catalytic system demonstrates broad substrate scope and high selectivity (>60 products were obtained in up to 99% isolated yield). The approach represents a user-friendly alternative for air-sensitive and labile (NHC)Ni0 and Ni(COD)2 precatalysts or complexes. The intermediates involved in the catalytic system were investigated and possible decomposition routes were mapped with NMR and ESI-MS. Rational control over the catalyst decomposition pathways further strengthens the sustainability of the procedure.
- Добавил в систему: Анаников Валентин Павлович