0000000001306104

AUTHOR

Konstantin V. Luzyanin

showing 19 related works from this author

PdII-mediated integration of isocyanides and azide ions might proceed via formal 1,3-dipolar cycloaddition between RNC ligands and uncomplexed azide

2016

Reaction between equimolar amounts of trans-[PdCl(PPh3)2(CNR)][BF4] (R = t-Bu 1, Xyl 2) and diisopropylammonium azide 3 gives the tetrazolate trans-[PdCl(PPh3)2(N4t-Bu)] (67%, 4) or trans-[PdCl(PPh3)2(N4Xyl)] (72%, 5) complexes. 4 and 5 were characterized by elemental analyses (C, H, N), HRESI+-MS, 1H and 13C{1H} NMR spectroscopies. In addition, the structure of 4 was elucidated by a single-crystal X-ray diffraction. DFT calculations showed that the mechanism for the formal cycloaddition (CA) of N3− to trans-[PdCl(PH3)2(CNMe)]+ is stepwise. The process is both kinetically and thermodynamically favorable and occurs via the formation of an acyclic NNNCN-intermediate. The second step of the fo…

010405 organic chemistryLigandStereochemistryIsocyanidechemistry.chemical_elementGeneral Chemistrypalladium complexes010402 general chemistry01 natural sciencesMedicinal chemistryCatalysisCycloadditionazides0104 chemical sciencesIonchemistry.chemical_compoundisocyanideschemistry13-Dipolar cycloadditionPotential energy surfaceMaterials ChemistryAzideta116PalladiumNew Journal of Chemistry
researchProduct

ADC-Based Palladium Catalysts for Aqueous Suzuki Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems

2013

The reaction between the equimolar amounts of cis-[PdCl2(CNR1)2] (R1 = cyclohexyl (Cy) (1), tBu (2)) and the carbohydrazides R2CONHNH2 (R2 = Ph (5), 4-ClC6H4 (6), 3-NO2C6H4 (7), 4-NO2C6H4 (8), 4-CH3C6H4 (9), 3,4-(MeO)2C6H3 (10), naphth-1-yl (11), fur-2-yl (12), 4-NO2C6H4CH2 (13), Cy (14), 1-(4-fluorophenyl)-5-oxopyrrolidin-3-yl (15), (pyrrolidin-1-yl)C(O) (16)) proceeds in refluxing CHCl3 for ca. 4 h. A subsequent workup provided the aminocarbene species cis-[PdCl2{C(NHNHC(O)R2)═N(H)R1}(CNR1)] (18–33) in good to excellent (80–95%) isolated yields. The coupling of equimolar amounts of cis-[PdCl2(CNR1)2] (R1 = Cy (1), tBu (2), 2,6-Me2C6H3 (Xyl) (3), 2-Cl-6-MeC6H3 (4)) and PhSO2NHNH2 (17) occu…

Inorganic ChemistryAqueous solutionchemistryStereochemistryOrganic Chemistrychemistry.chemical_elementNuclear magnetic resonance spectroscopyPhysical and Theoretical ChemistryCoupling (probability)Medicinal chemistryta116PalladiumCatalysisOrganometallics
researchProduct

Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling

2014

Abstract The metal-mediated coupling between cis-[PdCl2(CNR1)2] [R1 = cyclohexyl (Cy) 1, t-Bu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC6H3 4] and hydrazones H2NN CR2R3 [R2, R3 = Ph 5; R2, R3 = C6H4(OMe-4) 6; R2/R3 = 9-fluorenyl 7; R2 = H, R3 = C6H4(OH-2) 8] provided carbene complexes cis-[PdCl2{C(N(H)N CR2R3) N(H)R1}(CNR1)] (9–24) in good (80–85%) yields. Complexes 9–24 showed high activity [yields up to 99%, and turnover numbers (TONs) up to 3.7 × 104] in the Sonogashira coupling of various aryl iodides with a range of substituted aromatic alkynes without the need of copper co-catalyst. The catalytic procedure runs at 80 °C for 1 h in EtOH using K2CO3 as a base. No formation of homocoupling or ac…

Process Chemistry and TechnologyArylchemistry.chemical_elementSonogashira couplingDecompositionCopperMedicinal chemistryCatalysisCatalysischemistry.chemical_compoundAcetylenechemistryOrganic chemistryPhysical and Theoretical ChemistryCarbeneta116PalladiumJournal of Molecular Catalysis A: Chemical
researchProduct

Application of palladium complexes bearing acyclic amino(hydrazido)carbene ligands as catalysts for copper-free Sonogashira cross-coupling

2015

Abstract Metal-mediated coupling of one isocyanide in cis-[PdCl2(CNR1)2] (R1 = C6H11 (Cy) 1, tBu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC6H3 4) and various carbohydrazides R2CONHNH2 [R2 = Ph 5, 4-ClC6H4 6, 3-NO2C6H4 7, 4-NO2C6H4 8, 4-CH3C6H4 9, 3,4-(MeO)2C6H3 10, naphth-1-yl 11, fur-2-yl 12, 4-NO2C6H4CH2 13, Cy 14, 1-(4-fluorophenyl)-5-oxopyrrolidine-3-yl 15, (pyrrolidin-1-yl)C(O) 16, 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propane-1-yl 17, EtNHC(O) 18] or sulfohydrazides R3SO2NHNH2 [R3 = Ph 19, 4-MeC6H4 20] led to a series of (hydrazido)(amino)carbene complexes cis-[PdCl2{ C (NHNHX) N(H)R1}(CNR1)]; X = COR2, SO2R3 (21–48, isolated yields 60–96%). All prepared species were characterized by elemental…

StereochemistryIsocyanideArylchemistry.chemical_elementSonogashira couplingCopper-free Sonogashira couplingAcyclic diaminocarbenesNuclear magnetic resonance spectroscopyPalladium-(acyclic diminocarbene) catalystsMedicinal chemistryCatalysisCatalysischemistry.chemical_compoundchemistryCatalytic cycleMechanism of catalytic action of Pd-ADCsPhysical and Theoretical Chemistryta116CarbenePalladiumJournal of Catalysis
researchProduct

Palladium(II)-Mediated Addition of Benzenediamines to Isocyanides: Generation of Three Types of Diaminocarbene Ligands Depending on the Isomeric Stru…

2016

Coupling of the palladium-bis(isocyanide) complexes cis-[PdCl2(CNR)2] (R = 2,6-Me2C6H3 1, 2-Cl-6-MeC6H3 2) with benzene-1,3-diamine (BDA1) leads to the diaminocarbene species cis-[PdCl2(CNR){C(NHR)═NH(1,3-C6H4NH2)}] (5 and 6, respectively). In this reaction, BDA1 behaves as a monofunctional nucleophile that adds to one of the RNC ligands by one amino group. By contrast, the reaction of 1 and 2 with benzene-1,4-diamine (BDA2) involves both amino functionalities of the diamine and leads to the binuclear species [cis-PdCl2(CNR){μ-C(NHR)═NH(1,4-C6H4)NH═C(NHR)}-(cis)-PdCl2(CNR)] (6 and 7) featuring two 1,4-bifunctional diaminocarbene ligands. The reaction of cis-[PdCl2(CNR)2] (R = cyclohexyl 3) …

benzenediamines010405 organic chemistryStereochemistryIsocyanideOrganic Chemistrychemistry.chemical_elementdiaminocarbenespalladium complexes010402 general chemistry01 natural sciences0104 chemical sciencesInorganic Chemistrychemistry.chemical_compoundchemistryNucleophileDiamineisomersPhysical and Theoretical ChemistryCarbeneta116PalladiumOrganometallics
researchProduct

CCDC 912875: Experimental Crystal Structure Determination

2013

Related Article: Mikhail A. Kinzhalov, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Matti Haukka, and Vadim Yu. Kukushkin|2013|Organometallics|32|5212|doi:10.1021/om4007592

Space GroupCrystallographydichloro-((cyclohexylamino)(2-(phenylsulfonyl)hydrazino)methylene)-(cyclohexylisocyanido)-palladiumCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1501943: Experimental Crystal Structure Determination

2016

Related Article: Elena A. Valishina, M. Fátima C. Guedes da Silva, Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Tatyana M. Buslaeva, Matti Haukka, Armando J.L. Pombeiro , Vadim P. Boyarskiy, Vadim Yu. Kukushkin, Konstantin V. Luzyanin|2014|J.Mol.Catal.A:Chem.|395|162|doi:10.1016/j.molcata.2014.08.018

Space GroupCrystallography((2-(bis(4-methoxyphenyl)methylene)hydrazino)((26-dimethylphenyl)amino)methylene)-dichloro-(N-(26-dimethylphenyl)cyano)-palladiumCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1501944: Experimental Crystal Structure Determination

2016

Related Article: Elena A. Valishina, M. Fátima C. Guedes da Silva, Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Tatyana M. Buslaeva, Matti Haukka, Armando J.L. Pombeiro , Vadim P. Boyarskiy, Vadim Yu. Kukushkin, Konstantin V. Luzyanin|2014|J.Mol.Catal.A:Chem.|395|162|doi:10.1016/j.molcata.2014.08.018

Space GroupCrystallographyCrystal SystemCrystal Structuredichloro-(((26-dimethylphenyl)amino)(2-(9H-fluoren-9-ylidene)hydrazino)methylene)-((26-dimethylphenyl)cyano)-palladium chloroform solvateCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1435501: Experimental Crystal Structure Determination

2016

Related Article: Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Anton A. Yakimanskiy, Matti Haukka, Vadim Yu. Kukushkin|2016|Organometallics|35|218|doi:10.1021/acs.organomet.5b00936

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersbis((2-Amino-45-dimethylphenylamino)(2-chloro-6-methylphenylamino)methylidene-CN)-palladium(ii) dichloride acetonitrile solvateExperimental 3D Coordinates
researchProduct

CCDC 1435504: Experimental Crystal Structure Determination

2016

Related Article: Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Anton A. Yakimanskiy, Matti Haukka, Vadim Yu. Kukushkin|2016|Organometallics|35|218|doi:10.1021/acs.organomet.5b00936

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates((2-Amino-45-dimethylphenylamino)(2-chloro-6-methylphenylamino)methylidene-CN)-chloro-(N-(2-chloro-6-methylphenyl)cyano)-palladium(ii) chloride dichloromethane solvate
researchProduct

CCDC 1435506: Experimental Crystal Structure Determination

2016

Related Article: Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Anton A. Yakimanskiy, Matti Haukka, Vadim Yu. Kukushkin|2016|Organometallics|35|218|doi:10.1021/acs.organomet.5b00936

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersDichloro-((3-aminophenyl)(26-dimethylphenylamino)methylidene)-(N-(26-dimethylphenyl)cyano)-palladium(ii)Experimental 3D Coordinates
researchProduct

CCDC 912877: Experimental Crystal Structure Determination

2013

Related Article: Mikhail A. Kinzhalov, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Matti Haukka, and Vadim Yu. Kukushkin|2013|Organometallics|32|5212|doi:10.1021/om4007592

chloro-((cyclohexylamino)(2-(3-nitrobenzoyl)hydrazino)methylene)-(cyclohexylisocyanido)-(triphenylphosphine)-palladium chlorideSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 912876: Experimental Crystal Structure Determination

2013

Related Article: Mikhail A. Kinzhalov, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Matti Haukka, and Vadim Yu. Kukushkin|2013|Organometallics|32|5212|doi:10.1021/om4007592

Space GroupCrystallographydichloro-(((2-chloro-6-methylphenyl)amino)(2-(phenylsulfonyl)hydrazino)methylene)-((2-chloro-6-methylphenyl)isocyanido)-palladium dichloromethane solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1414621: Experimental Crystal Structure Determination

2015

Related Article: Mikhail A. Kinzhalov, Alexander S. Novikov, Konstantin V. Luzyanin, Matti Haukka, Armando J. L. Pombeiro, Vadim Yu. Kukushkin|2016|New J.Chem.|40|521|doi:10.1039/C5NJ02564H

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters(1-t-butyl-1H-tetrazol-5-yl)-chloro-bis(triphenylphosphine)-palladium(ii) 2-isopropoxypropane solvateExperimental 3D Coordinates
researchProduct

CCDC 1501945: Experimental Crystal Structure Determination

2016

Related Article: Elena A. Valishina, M. Fátima C. Guedes da Silva, Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Tatyana M. Buslaeva, Matti Haukka, Armando J.L. Pombeiro , Vadim P. Boyarskiy, Vadim Yu. Kukushkin, Konstantin V. Luzyanin|2014|J.Mol.Catal.A:Chem.|395|162|doi:10.1016/j.molcata.2014.08.018

Space GroupCrystallographydichloro-(((2-chloro-6-methylphenyl)amino)(2-(2-hydroxybenzylidene)hydrazino)methylene)-((2-chloro-6-methylphenyl)cyano)-palladiumCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1435500: Experimental Crystal Structure Determination

2016

Related Article: Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Anton A. Yakimanskiy, Matti Haukka, Vadim Yu. Kukushkin|2016|Organometallics|35|218|doi:10.1021/acs.organomet.5b00936

Space GroupCrystallographyCrystal System(mu2-NN'-bis(((2-Chloro-6-methylphenyl)amino)methylidene)benzene-14-diamine)-tetrachloro-bis((2-chloro-6-methylphenyl)isocyano)-di-palladium(ii) chloroform solvateCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1435503: Experimental Crystal Structure Determination

2016

Related Article: Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Anton A. Yakimanskiy, Matti Haukka, Vadim Yu. Kukushkin|2016|Organometallics|35|218|doi:10.1021/acs.organomet.5b00936

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters(NN'-bis(((2-Chloro-6-methylphenyl)amino)methylidene)-45-dichlorobenzene-12-diamine)-dichloro-palladium(ii) acetonitrile solvateExperimental 3D Coordinates
researchProduct

CCDC 1435502: Experimental Crystal Structure Determination

2016

Related Article: Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Anton A. Yakimanskiy, Matti Haukka, Vadim Yu. Kukushkin|2016|Organometallics|35|218|doi:10.1021/acs.organomet.5b00936

(NN'-bis(((2-Chloro-6-methylphenyl)amino)methylidene)-45-dimethylbenzene-12-diamine)-dichloro-palladium(ii) acetonitrile solvateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1435505: Experimental Crystal Structure Determination

2016

Related Article: Mikhail A. Kinzhalov, Svetlana A. Timofeeva, Konstantin V. Luzyanin, Vadim P. Boyarskiy, Anton A. Yakimanskiy, Matti Haukka, Vadim Yu. Kukushkin|2016|Organometallics|35|218|doi:10.1021/acs.organomet.5b00936

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters((2-Amino-45-dichlorophenylamino)(2-chloro-6-methylphenylamino)methylidene-CN)-chloro-((2-chloro-6-methylphenyl)isocyano)-palladium(ii) chloride dichloromethane solvateExperimental 3D Coordinates
researchProduct