Synthesis, microwave-promoted catalytic activity in Suzuki-Miyaura cross-coupling reactions and antimicrobial properties of novel benzimidazole salts bearing trimethylsilyl group

• Published in: Applied organometallic chemistry 2011-05, Vol.25 (5), p.366-373
• Main Authors: Yılmaz, Ülkü, Küçükbay, Hasan, Şireci, Nihat, Akkurt, Mehmet, Günal, Selami, Durmaz, Rıza, Nawaz Tahir, M.
• Format: Article
• Language: English
• Subjects: antimicrobial activity; benzimidazole salt; carbene; coupling reaction; Derivatives; Infrared radiation; Metalorganic compounds; microwave; Microwaves; palladium catalysis; Strain; Suzuki-Miyaura coupling; Synthesis; X-rays
• ISSN: 0268-2605; 1099-0739; 1099-0739
• DOI: 10.1002/aoc.1772

A mixture of benzimidazole salts (2–7), Pd(OAc)2 and K2CO3 in DMF–H2O catalyzes the Suzuki–Miyaura cross‐coupling reactions promoted by microwave irradiation resulting in high yield within a short time. In particular, the yield of the Suzuki–Miyaura reactions with aryl bromides was found to be nearly quantitative. The synthesized benzimidazole salts (2–7) were identified by 1H‐13C, NMR, IR spectroscopic methods and microanalysis. The molecular structure of 1 was determined by X‐ray crystallography. The antibacterial and antifungal activities of the novel benzimidazole derivatives (1–7) were also tested against standard strains. Copyright © 2011 John Wiley & Sons, Ltd. An efficient catalyst system, containing benzimidazolium salts bearing trimethylsilyl moieties in Suzuki–Miyaura reaction of aryl halides with phenylboronic acid under microwave irradiation, and antimicrobial activities of the benzimidazolium salts are reported.