893735-21-2Relevant academic research and scientific papers
New benzimidazolium N-heterocyclic carbene precursors and their related Pd-NHC complex PEPPSI-type: Synthesis, structures, DFT calculations, biological activity, docking study, and catalytic application in the direct arylation
?zdemir, ?smail,?zdemir, Nam?k,Bensouici, Chawki,Benzerka, Saida,Boulebd, Houssem,Gürbüz, Nevin,Khiri-Meribout, Naima,Sandeli, Abd El-Krim
, (2021/09/28)
New benzhydryl-5,6-dimethyl-(3-methylbenzyl)benzimidazolium salt as N-heterocyclic carbene precursors and their related new Pd-NHC complex PEPPSI-type with the general formula [PdBr2(NHC)(pyridine)] were prepared and theoretically studied. Quan
The first use of [PdBr2(imidazolidin-2-ylidene)(pyridine)] catalysts in the direct C-H bond arylation of C2-substituted furan and thiophene
Kalo?lu, Murat,Kalo?lu, Nazan,?zdemir, Nam?k,?zdemir, ?smail
, p. 2821 - 2843 (2021/04/21)
Abstract: N-Heterocyclic carbene (NHC)-linked PEPPSI-type palladium complexes have recently been used in the direct C-H bond arylation of heteroarenes. However, in most of the published works, NHC ligands containing benzimidazole and imidazole ring have b
Synthesis of [PdBr2(benzimidazole-2-ylidene)(pyridine)] complexes and their catalytic activity in the direct C[sbnd]H bond activation of 2-substituted heterocycles
Lasmari, Sarra,Gürbüz, Nevin,Boulcina, Raouf,?zdemir, Nam?k,?zdemir, ?smail
, (2021/02/27)
A series of unsymmetrical 1,3-disubstituted benzimidazolium chlorides, 2a-f, having two nitrogen atoms substituted by various alkyl groups were synthesized as N-heterocyclic carbene (NHC) precursors in high yields. The benzimidazolium salts are readily co
Synthesis of Quinoxaline-Linked Bis(Benzimidazolium) Salts and Their Catalytic Application in Palladium-Catalyzed Direct Arylation of Heteroarenes
?zdemir, ?smail,?ahan, Mehmet Hanifi,Dü?ünceli, Serpil Demir,Kalo?lu, Murat
, (2021/09/13)
Abstract: In this study, quinoxaline-linked bis(benzimidazolium) salts were synthesized as bis-N-heterocyclic carbene (NHC) precursors. These bis(NHC) precursors were used as multidentate ligands for the construction of bi(hetero)aryls by palladium-cataly
Synthesis, structures, DFT calculations, and catalytic application in the direct arylation of five-membered heteroarenes with aryl bromides of novel palladium-N-heterocyclic carbene PEPPSI-type complexes
?zdemir, ?smail,?zdemir, Nam?k,Benzerka, Saida,Boulebd, Houssem,Gürbüz, Nevin,Khiri-Meribout, Naima,el-Krim Sandeli, Abd
, p. 17878 - 17892 (2021/10/12)
A new series of Pd-catalysts based on an N-heterocyclic carbene PEPPSI-type ligand (PEPPSI = pyridine enhanced precatalyst preparation stabilization and initiation) with the general formula [Pd(ii)Br2(NHC)(pyridine)] was synthesized and fully characterize
PEPPSI-Type Palladium–NHC Complexes: Synthesis, Characterization, and Catalytic Activity in the Direct C5-Arylation of 2-Substituted Thiophene Derivatives with Aryl Halides
Kalo?lu, Murat,?zdemir, ?smail,Dorcet, Vincent,Bruneau, Christian,Doucet, Henri
, p. 1382 - 1391 (2017/03/31)
Six benzimidazolium salts, having two nitrogen atoms substituted by various alkyl groups, have been synthesized in high yields. The benzimidazolium salts readily converted into the corresponding PEPPSI-type palladium–NHC complexes (PEPPSI = pyridine-enhan
Solvent-free palladium-catalyzed direct arylation of heteroaromatics with aryl bromides
Bensaid, Souhila,Doucet, Henri
experimental part, p. 1559 - 1567 (2012/10/08)
Solvent is one of the major sources of waste in the course of catalyzed direct arylations. Some palladium-catalyzed direct arylations of heteroaromatics can be advantageously performed without any solvent. In the presence of palladium catalysts (1 mol%) and potassium acetate as the base, the direct 5-arylation of some thiazoles, thiophenes, furans, or pyrroles with aryl bromides as coupling partners proceeds highly regioselectively and in moderate to high yields. However, the use of these solvent-free conditions is limited to electron-deficient aryl bromides. Copyright
Analysis of the palladium-catalyzed (aromatic)C-H bond metalation- deprotonation mechanism spanning the entire spectrum of arenes
Gorelsky, Serge I.,Lapointe, David,Fagnou, Keith
experimental part, p. 658 - 668 (2012/03/11)
A comprehensive understanding of the C-H bond cleavage step by the concerted metalation-deprotonation (CMD) pathway is important in further development of cross-coupling reactions using different catalysts. Distortion-interaction analysis of the C-H bond cleavage over a wide range of (hetero)aromatics has been performed in an attempt to quantify the various contributions to the CMD transition state (TS). The (hetero)aromatics evaluated were divided in different categories to allow an easier understanding of their reactivity and to quantify activation characteristics of different arene substituents. The CMD pathway to the C-H bond cleavage for different classes of arenes is also presented, including the formation of pre-CMD intermediates and the analysis of bonding interactions in TS structures. The effects of remote C2 substituents on the reactivity of thiophenes were evaluated computationally and were corroborated experimentally with competition studies. We show that nucleophilicity of thiophenes, evaluated by Hammett σp parameters, correlates with each of the distortion-interaction parameters. In the final part of this manuscript, we set the initial equations that can assist in the development of predictive guidelines for the functionalization of C-H bonds catalyzed by transition metal catalysts.
DERIVATIVES OF SUBSTITUTED 3-PHENYL-1-(PHENYLTHIENYL)PROPAN-1-ONES AND OF 3-PHENYL-1-(PHENYLFURANYL) PROPAN-1-ONES, PREPARATION AND USE
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Page/Page column 12-13, (2010/03/02)
The present invention relates to compounds derived from substituted 3-phenyl-1-(thien-2-yl)propan-1-ones, pharmaceutical compositions comprising them as well as their therapeutic applications, notably in the field of human and animal health.
Ligand-less palladium-catalyzed direct 5-arylation of thiophenes at low catalyst loadings
Roger, Julien,Pozgan, Franc,Doucet, Henri
experimental part, p. 425 - 432 (2010/04/22)
Ligand-less Pd(OAc)2 provides a very efficient catalyst for the direct 5-arylation of thiophene derivatives. With this catalyst, a low palladium concentration (0.1-0.001 mol%) should be employed in order to obtain high yields of coupling products. At higher concentrations a fast formation of inactive "Pd black" generally occurs. Substrates/catalysts ratios up to 100000 can be employed with the most reactive aryl bromides. A very wide variety of functional groups is tolerated on both coupling partners. The major waste of this reaction is HBr associated with KOAc. Therefore this procedure is more economically and environmentally attractive than the traditional cross-coupling procedures employing organometallic derivatives.
