Erratum to: N-Propylphthalimide-Substituted Silver(I) N-Heterocyclic Carbene Complexes and Ruthenium(II) N-Heterocyclic Carbene Complexes: Synthesis and Transfer Hydrogenation of Ketones
TL;DR: In this article, the synthesis of N-propylphthalimide substituted Ag(I)-N-heterocyclic carbene (NHC) complexes and Npropyl-phthalimides substituted Ru(II)−NHC complexes has been investigated.
Abstract: This study deals with the synthesis of N-propylphthalimide substituted Ag(I)–N-heterocyclic carbene (NHC) complexes and N-propylphthalimide substituted Ru(II)–NHC complexes in the transfer hydrogenation of ketones. The Ag(I)–NHC complexes were synthesized from the imidazolium salts and Ag2O in dichloromethane at room temperature. The Ru(II)–NHC complexes have been prepared from Ag(I)–NHC complexes using transmetallation method. The six N-propylphthalimide substituted Ag(I)–NHC complexes and six N-propylphthalimide substituted Ru(II)–NHC complexes have been characterized by spectroscopic techniques and elemental analyses. N-propylphthalimide substituted Ru(II)–NHC complexes have been analyzed as catalysts for the transfer hydrogenation of ketones and exhibit activity in this reaction. This study deals with the synthesis of N-propylphthalimide substituted Ag(I)-N-heterocyclic carbene (NHC) complexes and N-propylphthalimide substituted Ru(II)–NHC complexes in the transfer hydrogenation of ketones. The Ag(I)–NHC complexes were synthesized from the imidazolium salts and Ag2O in dichloromethane at room temperature. The Ru(II)–NHC complexes have been prepared from Ag(I)–NHC complexes using transmetallation method. The six N-propylphthalimide substituted Ag(I)–NHC complexes and six N-propylphthalimide substituted Ru(II)–NHC complexeshavebeencharacterizedbyspectroscopictechniquesandelementalanalyses. N-propylphthalimide substituted Ru(II)–NHC complexes have been analyzed as catalysts for the transfer hydrogenation of ketones and exhibit activity in this reaction.
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1,307 citations
TL;DR: This study contains novel a serie synthesis of N-heterocyclic carbene (NHC) precursors that 2-hydroxyethyl substituted that effectively inhibited the α-glycosidase, cytosolic carbonic anhydrase I and II isoforms, butyrylcholinesterase (BChE) and acetylcholinease (AChE).
119 citations
TL;DR: Three series of imidazolidinium ligands substituted with 4‐vinylbenzyl, 2‐methyl‐1,4‐benzodioxane, and N‐propylphthalimide were synthesized and the inhibitory effects of the novel synthesized NHCs were compared to acetazolamide as a clinical CA isoenzymes inhibitor and tacrine as aclinical cholinergic enzymes inhibitor.
Abstract: Three series of imidazolidinium ligands (NHC precursors) substituted with 4-vinylbenzyl, 2-methyl-1,4-benzodioxane, and N-propylphthalimide were synthesized. N-Heterocyclic carbene (NHC) precursors were prepared from N-alkylimidazoline and alkyl halides. The novel NHC precursors were characterized by 1H NMR, 13C NMR, FTIR spectroscopy, and elemental analysis techniques. The enzymes inhibition activities of the NHC precursors were investigated against the cytosolic human carbonic anhydrase I and II isoenzymes (hCA I and II) and the acetylcholinesterase (AChE) enzyme. The inhibition parameters (IC50 and Ki values) were calculated by spectrophotometric method. The inhibition constants (Ki) were found to be in the range of 166.65–635.38 nM for hCA I, 78.79–246.17 nM for hCA II, and 23.42–62.04 nM for AChE. Also, the inhibitory effects of the novel synthesized NHCs were compared to acetazolamide as a clinical CA isoenzymes inhibitor and tacrine as a clinical cholinergic enzymes inhibitor.
75 citations
TL;DR: In this paper, a brief overview of advances on ruthenium(II) N-heterocyclic carbene complexes (NHCs) applied for hydrogenation reactions undertaken during the last five years is provided.
66 citations
TL;DR: The derivatives of these novel NHC precursors were effective inhibitors of α‐glycosidase (AG), the cytosolic carbonic anhydrase I and II isoforms, butyrylcholinesterase (BChE), and acetylcholinerase (AChE) with Ki values in the range of 1.01–2.18.
Abstract: meta-Cyanobenzyl-substituted N-heterocyclic carbene (NHC) precursors were synthesized by the reaction of a series of N-(alkyl)benzimidazolium with 3-bromomethyl-benzonitrile. These benzimidazolium salts were characterized by using 1 H NMR, 13 C NMR, FTIR spectroscopy, and elemental analysis techniques. The molecular and crystal structures of 2f and 2g complexes were obtained by using the single-crystal X-ray diffraction method. The derivatives of these novel NHC precursors were effective inhibitors of α-glycosidase (AG), the cytosolic carbonic anhydrase I and II isoforms (hCA I and II), butyrylcholinesterase (BChE), and acetylcholinesterase (AChE) with Ki values in the range of 1.01-2.12 nM for AG, 189.56-402.44 nM for hCA I, 112.50-277.37 nM for hCA II, 95.45-352.58 nM for AChE, and 132.91-571.18 nM for BChE. In the last years, inhibition of the CA enzyme has been considered as a promising factor for pharmacologic intervention in a diversity of disturbances such as obesity, glaucoma, cancer, and epilepsy.
60 citations
References
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TL;DR: Synthese, structure et caracterisation du (1,3-bis [1-adamantyl]-2, 3-dihydro)-2,carbenoimidazole prepare par deprotonation du chlorure de (1 3-bis] [1]- imidazolium as discussed by the authors.
Abstract: Synthese, structure et caracterisation du (1,3-bis [1-adamantyl]-2,3-dihydro)-2-carbenoimidazole prepare par deprotonation du chlorure de (1,3-bis [1-adamantyl]) imidazolium
3,414 citations
TL;DR: N-Heterocyclic carbenes have become universal ligands in organometallic and inorganic coordination chemistry as mentioned in this paper, and they not only bind to any transition metal, be it in low or high oxidation states, but also to main group elements such as beryllium, sulfur, and iodine.
Abstract: N-Heterocyclic carbenes have become universal ligands in organometallic and inorganic coordination chemistry. They not only bind to any transition metal, be it in low or high oxidation states, but also to main group elements such as beryllium, sulfur, and iodine. Because of their specific coordination chemistry, N-heterocyclic carbenes both stabilize and activate metal centers in quite different key catalytic steps of organic syntheses, for example, C-H activation, C-C, C-H, C-O, and C-N bond formation. There is now ample evidence that in the new generation of organometallic catalysts the established ligand class of organophosphanes will be supplemented and, in part, replaced by N-heterocyclic carbenes. Over the past few years, this chemistry has been the field of vivid scientific competition, and yielded previously unexpected successes in key areas of homogeneous catalysis. From the work in numerous academic laboratories and in industry, a revolutionary turning point in oraganometallic catalysis is emerging.
3,388 citations
Book•
13 Aug 1993
TL;DR: Asymmetric Hydrogenation (T. Ohkuma, et al. as discussed by the authors ), asymmetric carbon-Carbon Bond-Forming Reactions (K. Nozaki & I. Negishi). Asymmetric Addition and Insertion Reactions of Catalytically-Generated Metal Carbenes (M. O'Donnell), and asymptotic phase-transfer Reactions.
Abstract: Asymmetric Hydrogenation (T. Ohkuma, et al.). Asymmetric Hydrosilylation and Related Reactions (H. Nishiyama & K. Itoh). Asymmetric Isomerization of Allylamines (S. Akutagawa, et al.). Asymmetric Carbometallations (E. Negishi). Asymmetric Addition and Insertion Reactions of Catalytically-Generated Metal Carbenes (M. Doyle). Asymmetric Oxidations and Related Reactions (R. Johnson, et al.). Asymmetric Carbonylations (K. Nozaki & I. Ojima). Asymmetric Carbon-Carbon Bond-Forming Reactions (K. Maruoka, et al.). Asymmetric Amplification and Autocatalysis (K. Soai & T. Shibata). Asymmetric Phase-Transfer Reactions (M. O'Donnell). Asymmetric Polymerization (Y. Okamoto & T. Nakano). Epilogue. Appendix. Index.
2,758 citations
TL;DR: In this paper, the reactions of RuCl2(PPh3)3 with a number of diazoalkanes were surveyed, and alkylidene transfer was observed for RCHN2 and various para-substituted aryl diazalkanes p-C6H4X CHN2.
Abstract: The reactions of RuCl2(PPh3)3 with a number of diazoalkanes were surveyed, and alkylidene transfer to give RuCl2(CHR)(PPh3)2 (R = Me (1), Et (2)) and RuCl2(CH-p-C6H4X)(PPh3)2 (X = H (3), NMe2 (4), OMe (5), Me (6), F (7), Cl (8), NO2 (9)) was observed for alkyl diazoalkanes RCHN2 and various para-substituted aryl diazoalkanes p-C6H4XCHN2. Kinetic studies on the living ring-opening metathesis polymerization (ROMP) of norbornene using complexes 3−9 as catalysts have shown that initiation is in all cases faster than propagation (ki/kp = 9 for 3) and that the electronic effect of X on the metathesis activity of 3−9 is relatively small. Phosphine exchange in 3−9 with tricyclohexylphosphine leads to RuCl2(CH-p-C6H4X)(PCy3)2 10−16, which are efficient catalysts for ROMP of cyclooctene (PDI = 1.51−1.63) and 1,5-cyclooctadiene (PDI = 1.56−1.67). The crystal structure of RuCl2(CH-p-C6H4Cl)(PCy3)2 (15) indicated a distorted square-pyramidal geometry, in which the two phosphines are trans to each other, and the alkyli...
1,957 citations
TL;DR: The Role of the "Tebbe Complex" in Olefin Metathesis is discussed in this paper, where the discovery of well-defined Ruthenium Olefin metathesis Catalysts is discussed.
Abstract: Preface.CATALYST DEVELOPMENTS.Introduction.The Role of the "Tebbe Complex" in Olefin Metathesis.The Discovery and Development of High Oxidation State Mo and W Imido Alkylidene Complexes for Alkene Metathesis.From ill-defined to well-defined W alkylidene complexes.Discovery of Well-defined Ruthenium Olefin Metathesis Catalysts.Synthesis of Ruthenium Carbene Complexes.ynthesis of Rhodium and Ruthenium Carbene Complexes with a 16-Electron Count.Mechanism of Ruthenium-Catalyzed Olefin Metathesis Reactions.Intrinsic Reactivity of Ruthenium Carbenes.The Discovery and Development of High Oxidation State Alkylidyne Complexes for Alkyne Metathesis.Well-defined Metallocarbenes and Metallocarbynes Supported on Oxide Support prepared via Surface Organometallic Chemistry.APPLICATIONS IN ORGANIC SYNTHESIS.Introduction.General Ring-Closing Metathesis.Catalytic Asymmetric Olefin Metathesis.Tandem RCM.Ene-Yne Metathesis.Ring Opening Cross Metathesis.Ring Expansion Metathesis Reactions.Olefin Cross-Metathesis.The Olefin Metathesis Reaction in Complex Molecule Construction.Applications of Ring Closing Metathesis to Alkaloid Synthesis.Radicicol and the Epothilones: Total Synthesis of Novel Anti Cancer Agents Using Ring Closing Metathesis.The Use of Olefin Metathesis in Combinatorial Chemistry: Supported and Chromatography-Free Syntheses.Metal-Catalyzed Olefin Metathesis in Metal Coordination Spheres.Alkyne Metathesis.Metathesis of silicon-containing olefins.Commercial Applications of Ruthenium Metathesis Processes.POLYMER SYNTHESIS.Introduction.Living Ring-Opening Olefin Metathesis Polymerization.Synthesis of Copolymers.Conjugated polymers.Stereochemistry of ROMP.Syntheses and Applications of Bioactive Polymers Generated by the Ring-Opening Metathesis Polymerization (ROMP).Metathesis Polymerization: A Versatile Tool for the Synthesis of Surface-Functionalized Supports and Monolithic Materials.Telechelic Polymers from Olefin Metathesis Methodologies.ADMET Polymerization.Acyclic Diyne Metathesis Utilizing in Situ Transition Metal Catalysts: An Efficient Access to Alkyne-Bridged Polymers.Polymerization of Substituted Acetylenes.Commercial Applications.
1,565 citations