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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F14%3A10271763%21RIV15-MSM-11310___
rdf:type
skos:Concept n17:Vysledek
rdfs:seeAlso
http://dx.doi.org/10.1021/om500342z
dcterms:description
Six palladium(II) complexes bearing three different triazole-based N-heterocyclic carbene (NHC) ligands, [1-tert-butyl-4-{2-[(N,N-dimethylamino)methyl]phenyl}-3-phenyl-1H-1,2,4- triazol-4-ium-5-ide, 1-tert-butyl-4-(2-methoxyphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide, and 1-tert-butyl-4-(4-methylphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide], were synthesized and fully characterized. NMR spectroscopy and X-ray diffraction analysis revealed that the amino-group-substituted NHC ligand is coordinated in bidentate fashion, forming a monocarbene chelate complex with an additional intramolecular Pd <- N bond with the nitrogen donor atom. The 4-methylphenyl- and 2-methoxyphenyl-substituted NHC ligands coordinate as C-monodentate donors, forming simple biscarbene Pd(II) complexes. The evaluation of the catalytic performance in the Suzuki-Miyaura cross-coupling reaction revealed very promising performance of the intramolecularly coordinated monocarbene complexes under relatively mild conditions even in direct comparison with the commercially available PEPPSI catalyst. In contrast, the biscarbene complexes proved inactive in this catalytic process. According to theoretical calculations (EDA and NOCV analysis), functionalization of the 1,2,4-triazole-based NHC with the 2-[(N,N-dimethylamino)methyl]phenyl group has a significant effect on the stability of the NHC metal bond. Six palladium(II) complexes bearing three different triazole-based N-heterocyclic carbene (NHC) ligands, [1-tert-butyl-4-{2-[(N,N-dimethylamino)methyl]phenyl}-3-phenyl-1H-1,2,4- triazol-4-ium-5-ide, 1-tert-butyl-4-(2-methoxyphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide, and 1-tert-butyl-4-(4-methylphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide], were synthesized and fully characterized. NMR spectroscopy and X-ray diffraction analysis revealed that the amino-group-substituted NHC ligand is coordinated in bidentate fashion, forming a monocarbene chelate complex with an additional intramolecular Pd <- N bond with the nitrogen donor atom. The 4-methylphenyl- and 2-methoxyphenyl-substituted NHC ligands coordinate as C-monodentate donors, forming simple biscarbene Pd(II) complexes. The evaluation of the catalytic performance in the Suzuki-Miyaura cross-coupling reaction revealed very promising performance of the intramolecularly coordinated monocarbene complexes under relatively mild conditions even in direct comparison with the commercially available PEPPSI catalyst. In contrast, the biscarbene complexes proved inactive in this catalytic process. According to theoretical calculations (EDA and NOCV analysis), functionalization of the 1,2,4-triazole-based NHC with the 2-[(N,N-dimethylamino)methyl]phenyl group has a significant effect on the stability of the NHC metal bond.
dcterms:title
Palladium(II) Complexes of 1,2,4-Triazole-Based N-Heterocyclic Carbenes: Synthesis, Structure, and Catalytic Activity Palladium(II) Complexes of 1,2,4-Triazole-Based N-Heterocyclic Carbenes: Synthesis, Structure, and Catalytic Activity
skos:prefLabel
Palladium(II) Complexes of 1,2,4-Triazole-Based N-Heterocyclic Carbenes: Synthesis, Structure, and Catalytic Activity Palladium(II) Complexes of 1,2,4-Triazole-Based N-Heterocyclic Carbenes: Synthesis, Structure, and Catalytic Activity
skos:notation
RIV/00216208:11310/14:10271763!RIV15-MSM-11310___
n5:aktivita
n8:I n8:S n8:P
n5:aktivity
I, P(GA104/09/0561), P(GAP207/12/0223), S
n5:cisloPeriodika
12
n5:dodaniDat
n13:2015
n5:domaciTvurceVysledku
n10:8116997 n10:3492389
n5:druhVysledku
n6:J
n5:duvernostUdaju
n20:S
n5:entitaPredkladatele
n11:predkladatel
n5:idSjednocenehoVysledku
35631
n5:idVysledku
RIV/00216208:11310/14:10271763
n5:jazykVysledku
n15:eng
n5:klicovaSlova
density-functional theory; structure elucidation; homogeneous catalysis; suzuki-miyaura reaction; cross-coupling reactions; palladium complexes; carbene ligands
n5:klicoveSlovo
n7:homogeneous%20catalysis n7:density-functional%20theory n7:carbene%20ligands n7:palladium%20complexes n7:cross-coupling%20reactions n7:structure%20elucidation n7:suzuki-miyaura%20reaction
n5:kodStatuVydavatele
US - Spojené státy americké
n5:kontrolniKodProRIV
[494ADFC8F3F1]
n5:nazevZdroje
Organometallics
n5:obor
n18:CA
n5:pocetDomacichTvurcuVysledku
2
n5:pocetTvurcuVysledku
7
n5:projekt
n16:GAP207%2F12%2F0223 n16:GA104%2F09%2F0561
n5:rokUplatneniVysledku
n13:2014
n5:svazekPeriodika
33
n5:tvurceVysledku
Semler, Miloslav Padělková, Zdeňka De Proft, Frank Růžička, Aleš Štěpnička, Petr Panov, Illia Turek, Jan
n5:wos
000337936800020
s:issn
0276-7333
s:numberOfPages
11
n19:doi
10.1021/om500342z
n14:organizacniJednotka
11310