Synthesis of N-heterocyclic carbene-palladium-PEPPSI complexes and their catalytic activity in the direct C-H bond activation
| Autor: | Murat Kaloğlu, Nazan Kaloğlu, Muhammad Tahir, Pierre H. Dixneuf, Cengiz Arıcı, Henri Doucet, İsmail Özdemir, Christian Bruneau, Bekir Çetinkaya |
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| Přispěvatelé: | Inönü University, University of Sargodha, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Ege University (EGE), 109T605, B.A.P. 2015/41, Institut des Sciences Chimiques de Rennes ( ISCR ), Université de Rennes 1 ( UR1 ), Université de Rennes ( UNIV-RENNES ) -Université de Rennes ( UNIV-RENNES ) -Ecole Nationale Supérieure de Chimie de Rennes-Institut National des Sciences Appliquées ( INSA ) -Centre National de la Recherche Scientifique ( CNRS ), Ege University ( EGE ), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Infrared spectroscopy
chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound [ CHIM.CATA ] Chemical Sciences/Catalysis pyrroles Materials Chemistry Molecule Organic chemistry [CHIM.COOR]Chemical Sciences/Coordination chemistry Physical and Theoretical Chemistry ComputingMilieux_MISCELLANEOUS Pyrrole 010405 organic chemistry Aryl Organic Chemistry direct arylation [ CHIM.COOR ] Chemical Sciences/Coordination chemistry [CHIM.CATA]Chemical Sciences/Catalysis 3. Good health 0104 chemical sciences PEPPSI chemistry Benzimidazolium salts Carbene N-heterocyclic carbene PEPPSI-type palladium-NHC complexes Palladium |
| Zdroj: | Journal of Organometallic Chemistry Journal of Organometallic Chemistry, Elsevier, 2018, 867, pp.404-412. ⟨10.1016/j.jorganchem.2017.10.019⟩ Journal of Organometallic Chemistry, Elsevier, 2018, 867, pp.404-412. 〈10.1016/j.jorganchem.2017.10.019〉 Journal of Organometallic Chemistry, 2018, 867, pp.404-412. ⟨10.1016/j.jorganchem.2017.10.019⟩ |
| ISSN: | 0022-328X |
| DOI: | 10.1016/j.jorganchem.2017.10.019⟩ |
| Popis: | A series of benzimidazolium salts having their two nitrogen atoms substituted by bulky groups have been synthesized. The benzimidazolium salts were readily converted into the corresponding palladium-NHC-PEPPSI complexes with general formula [PdBr2(NHC) (Py)], (NHC = N-heterocyclic carbene; PEPPSI = pyridine-enhanced precatalyst preparation, stabilisation, and initiation). The structures of all new compounds were characterized by NMR, IR spectroscopy and microanalysis techniques, which support the proposed structures. The molecular structure of complex 2g was determined by singlecrystal X-ray diffraction study. Next, the palladium-NHC-PEPPSI complexes were used as catalysts in the direct C5-arylation of 1-methylpyrrole-2-carboxaldehyde by aryl halides. These complexes exhibited moderate to high catalytic activities and gave C-H activation selectively at the C5-position of 1methylpyrrole- 2-carboxaldehyde. Both electron-donating and electron-withdrawing substituents were well tolerated with catalytic systems based on these complexes, even non-activated aryl chlorides such as chlorobenzene or 4-chlorotoluene were coupled with pyrrole in moderate yields. (C) 2017 Elsevier B.V. All rights reserved. |
| Databáze: | OpenAIRE |
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