title: N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd-NHC complexes: synthesis, characterization and catalytic activity in carbon-carbon bond-forming reactions.
abstract: A series of novel benzimidazolium salts (1-4) and their pyridine enhanced precatalyst preparation stabilization and initiation (PEPPSI) themed palladium N-heterocyclic carbene complexes [PdCl2(NHC)(Py)] (5-8), where NHC = 1-(N-methylphthalimide)-3-alkylbenzimidazolin-2-ylidene and Py = 3-chloropyridine, were synthesized and characterized by means of (1)H and (13)C{(1)H} NMR, UV-vis (for 5-8), ESI-FTICR-MS (for 2, 4, 6-8) and FTIR spectroscopic methods and elemental analysis. The synthesized compounds were tested in Suzuki-Miyaura cross-coupling (for 1-8) and arylation (for 5-8) reactions. As catalysts, they demonstrated a highly efficient route for the formation of asymmetric biaryl compounds even though they were used in very low loading. For example, all compounds displayed good catalytic activity for the C-C bond formation of 4-tert-butylphenylboronic acid with 4-chlorotoluene.
authors.affiliation: Faculty of Pharmacy, The University of Sydney, 2006 Sydney, Australia; Department of Chemistry, Faculty of Sciences, Erciyes University, Talas Street, 38039 Kayseri, Turkey.
authors.forename: Senem
authors.initials: S
authors.lastname: Akkoç
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Inönü University, 44280 Malatya, Turkey.
authors.forename: Yetkin
authors.initials: Y
authors.lastname: Gök
authors.affiliation: Department of Chemistry, Faculty of Sciences, Erciyes University, Talas Street, 38039 Kayseri, Turkey.
authors.forename: İlhan Özer
authors.initials: İÖ
authors.lastname: İlhan
authors.affiliation: Faculty of Pharmacy, The University of Sydney, 2006 Sydney, Australia.
authors.forename: Veysel
authors.initials: V
authors.lastname: Kayser
keywords: N-heterocyclic carbene; PEPPSI complex; Suzuki–Miyaura cross-coupling reaction; arylation; benzimidazolium salts; catalysis