Bugday, NesrinKhan, SirajYasar, SedatOzdemir, Ismail2024-08-042024-08-0420210022-328X1872-8561https://doi.org/10.1016/j.jorganchem.2021.121730https://hdl.handle.net/11616/99780A highly efficient and effective protocol has been developed for the synthesis of C5-(hetero)arylated 2-isobutylthiazole derivatives. Four different palladium N-heterocyclic carbene (Pd-NHCs) complexes [Pd(mu-Cl)Cl(SIMes)](2) (2), (LCl2 Pd-SIMes) (3: L = PPh3; 4: L = Py; 5: L = 3-CHO-Py) were synthesized and used for the first time as a catalysts in direct C-H arylation reaction of 2-isobutylthiazole at C5 position. Utilizations of these catalytic systems, the arylation of 2-isobutylthiazole with substituted (hetero)aryl bromides efficiently proceeded at low catalyst loading (1 mol%) and without any additives such as PivOH under argon or aerobic conditions at 120 degrees C in a short time. Different substituted (hetero)aryl bromides, even some deactivated or highly sterically hindered (hetero)arylbromides, with a wide range of functional groups were successfully utilized under the optimum reaction conditions. In all cases, the C5 arylated 2-isobutylthiazoles were obtained in moderate to excellent yields. (C) 2021 Elsevier B.V. All rights reserved.eninfo:eu-repo/semantics/closedAccessPalladiumC-H activationdirect arylationThiazoleN-heterocyclic carbeneArticle93710.1016/j.jorganchem.2021.1217302-s2.0-85101349757Q3WOS:000632248200010Q2