[HTML][HTML] N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: synthesis, characterization and catalytic activity in carbon–carbon …
Beilstein Journal of Organic Chemistry, 2016•beilstein-journals.org
A series of novel benzimidazolium salts (1–4) and their pyridine enhanced precatalyst
preparation stabilization and initiation (PEPPSI) themed palladium N-heterocyclic carbene
complexes [PdCl 2 (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 …
preparation stabilization and initiation (PEPPSI) themed palladium N-heterocyclic carbene
complexes [PdCl 2 (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 …
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 [PdCl 2 (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.
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