Autor: Janíková, K.; Jedinák, L.; Volná, T.; Cankař, P.
Název práce v češtině: Chan-Lam reakce za katalýzy systémem Cu2S/TMEDA
Název práce v angličtině: Chan-​Lam cross-​coupling reaction based on the Cu2S​/TMEDA system
Studentská publikace: ano
Klíčová slova v češtině: Chan-Lam, sulfid měďný, imidazol, benzimidazol, arylace
Klíčová slova v angličtině: Chan-Lam coupling, Copper(I) sulfide, Arylation, Imidazole, Benzimidazole
Abstrakt česky: Byl vyvinut katalýzátor založený na systému TMEDA/Cu2S pro N-arylace dusíkatých heterocyklů – imidazolu a benzimidazolu. Metoda toleruje různě substituované arylboronové kyseliny včetně OH skupiny a ortho substituentů. Ortho substituce u některých derivátů benzimidazolonu vedla k pozorování spomalené rotaci kolem C-N vazby (atropoizomerie). Vyvinuté podmínky umožňují kombinovat v tandemu Chan-Lam a Suzuki-Miyaura cross-coupling.
Abstrakt anglicky: A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted CN bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported. .
Jazyk v originále: AJ
Název časopisu: Tetrahedron
Rok: 2018
Svazek (ročník): 74
Číslo časopisu v rámci uvedeného svazku: 5
Strana od-do: 606-617

Q1: ne

ISSN časopisu: 0040-4020
Vydavatel: Elsevier
Způsob financování: This work was supported by the Czech National Program for Sustainability (project LO1304), the Operational Programme Enterprise and Innovations for Competitiveness (project CZ.01.1.02/0.0/0.0/15_019/0004431), and the internal Palacky University IGA projects (IGA_PrF_2017_009 and IGA_LF_2017_028).
DOI: 10.1016/j.tet.2017.12.042