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Selective Buchwald–Hartwig arylation of $\less$i$\greater$C$\less$/i$\greater$-amino-1,2,4-triazoles and other coordinating aminoheterocycles enabled by bulky NHC ligands and TPEDO activatorстатья
Статья опубликована в высокорейтинговом журнале
Статья опубликована в журнале из списка Web of Science и/или Scopus- Авторы: Astakhov Alexander V., Chernenko Andrey Yu, Kutyrev Vadim V., Ranny Gleb S., Minyaev Mikhail E., Chernyshev Victor M., Ananikov Valentine P.
- Журнал: INORGANIC CHEMISTRY FRONTIERS
- Том: 10
- Номер: 1
- Год издания: 2023
- Первая страница: 218
- Последняя страница: 239
- DOI: 10.1039/d2qi01832b
- Аннотация: C-Amino-1,2,4-triazoles are challenging polynitrogen substrates for metal-catalyzed arylation due to their multidentate character, enhanced coordinating ability and decreased nucleophilicity of the amino group. In the present study, the Buchwald–Hartwig cross-coupling of diverse 3(5)-amino-1,2,4-triazoles with aryl chlorides and bromides delivering (hetero)arylamino-1,2,4-triazoles in good-to-excellent yields under Pd/NHC catalysis was developed. The use of Pd complexes with bulky NHC ligands such as IPr*OMe and TPEDO (1,1,2,2-tetraphenylethane-1,2-diol) as an in situ Pd(II) to Pd(0) reductant enabled the selective arylation of the NH2 group even in acidic NH unprotected substrates and deactivated 1-substituted 5-amino- and 4-substituted 3-amino-1,2,4-triazoles. The reaction mechanism and structure–activity relationships were studied with DFT calculations. A significant effect of the position of the N-substituent in the 1,2,4-triazole ring on the favorable reaction pathways was revealed.
- Добавил в систему: Анаников Валентин Павлович