Synthesis, structures, and norbornene polymerization behavior of palladium methyl complexes bearing N-heterocyclic carbene-sulfonate ligands

Li, Minliang; Song, Haibin; Wang, Baiquan

doi:10.1016/j.jorganchem.2015.12.045

Cited by 18 publications

(4 citation statements)

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“…Catalyst 5 was also examined because it has been shown to be highly recyclable under aqueous reaction conditions in allylic alcohol isomeroizations . These complexes are part of a larger set of structurally similar sulfonated N-heterocyclic carbene complexes of platinum group metals, − which are likely to share some reactivity trends and decomposition patterns with the catalysts discussed hrerein.…”

Section: Resultsmentioning

confidence: 99%

Transfer Hydrogenation from Glycerol: Activity and Recyclability of Iridium and Ruthenium Sulfonate-Functionalized N-Heterocyclic Carbene Catalysts

Azua

Finn

et al. 2017

ACS Sustainable Chem. Eng.

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Three ruthenium(II) and two iridium(III) N-heterocyclic carbene (NHC) complexes functionalized with sulfonates are compared with respect to their activity and selectivity for the transfer hydrogenation of imines, aldehydes, ketones, and olefins using neat glycerol as hydrogen donor and solvent. Four of the five catalysts likely proceed through a monohydride mechanism and are more active for transfer hydrogenation of imines than aldehydes, ketones, and olefins. The fifth catalyst likely proceeds through a dihydride mechanism and is found to be more active for carbonyls than imines and olefins. Lactic acid is observed as the only detectable byproduct from glycerol. Quantitative poisoning experiments with 1,10-phenanthroline suggest that the predominant catalytically active species is a ligated homogeneous complex with weak binding to the poison. The potential for catalyst recycling is explored: the ruthenium NHC catalysts with chelating ligands are found to be more robust and recyclable relative to the iridium catalysts and the ruthenium mono-NHC catalyst. The reason is traced to the relative rate of degradation of the catalyst in the presence of glycerol and KOH but no substrate. This degradation is only observed when glycerol is used, as replacing glycerol with isopropanol allows the ruthenium catalyst to be fully recyclable.

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Section: Resultsmentioning

confidence: 99%

Transfer Hydrogenation from Glycerol: Activity and Recyclability of Iridium and Ruthenium Sulfonate-Functionalized N-Heterocyclic Carbene Catalysts

Azua

Finn

et al. 2017

ACS Sustainable Chem. Eng.

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“…A large number of complexes with NHC ligands with oxygen donor groups have also been extensively studied. These may contain alcohol, − alkoxide, ,− phenoxide, − ether, ,− sulfonate, − or carboxylate groups. Some selected recent examples of this type of complexes are depicted in Chart .…”

Section: Multifunctional N-heterocyclic Carbene Ligandsmentioning

confidence: 99%

Smart N-Heterocyclic Carbene Ligands in Catalysis

2017

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It is well-recognized that N-heterocyclic carbene (NHC) ligands have provided a new dimension to the design of homogeneous catalysts. Part of the success of this type of ligands resides in the limitless access to a variety of topologies with tuned electronic properties, but also in the ability of a family of NHCs that are able to adapt their properties to the specific requirements of individual catalytic transformations. The term "smart" is used here to refer to switchable, multifunctional, adaptable, or tunable ligands and, in general, to all those ligands that are able to modify their steric or electronic properties to fulfill the requirements of a defined catalytic reaction. The purpose of this review is to comprehensively describe all types of smart NHC ligands by focusing attention on the catalytically relevant ligand-based reactivity.

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“…Pd/NHC complexes (NHC -N-heterocyclic carbene) have proven to play important roles in various fields of chemistry, such as cross-coupling reactions, polymerization reactions, and other catalytic processes. [1][2][3][4][5][6][7][8][9][10][11] Their main advantages include a tunable electron-transfer ability to metal centers, as well as the ability to control the electronic and steric effects for each specific task by changing the substituents at nitrogen atoms. [12][13][14][15][16][17] There are a large number of studies devoted to the variation of steric bulk and electronic parameters of M/NHC complexes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and a combined experimental/theoretical structural study of a comprehensive set of Pd/NHC complexes witho-,m-, andp-halogen-substituted aryl groups (X = F, Cl, Br, CF₃)

et al. 2023

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Synthesis, structures, and norbornene polymerization behavior of palladium methyl complexes bearing N-heterocyclic carbene-sulfonate ligands

Cited by 18 publications

References 84 publications

Transfer Hydrogenation from Glycerol: Activity and Recyclability of Iridium and Ruthenium Sulfonate-Functionalized N-Heterocyclic Carbene Catalysts

Transfer Hydrogenation from Glycerol: Activity and Recyclability of Iridium and Ruthenium Sulfonate-Functionalized N-Heterocyclic Carbene Catalysts

Smart N-Heterocyclic Carbene Ligands in Catalysis

Synthesis and a combined experimental/theoretical structural study of a comprehensive set of Pd/NHC complexes witho-,m-, andp-halogen-substituted aryl groups (X = F, Cl, Br, CF₃)

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Synthesis, structures, and norbornene polymerization behavior of palladium methyl complexes bearing N-heterocyclic carbene-sulfonate ligands

Cited by 18 publications

References 84 publications

Transfer Hydrogenation from Glycerol: Activity and Recyclability of Iridium and Ruthenium Sulfonate-Functionalized N-Heterocyclic Carbene Catalysts

Transfer Hydrogenation from Glycerol: Activity and Recyclability of Iridium and Ruthenium Sulfonate-Functionalized N-Heterocyclic Carbene Catalysts

Smart N-Heterocyclic Carbene Ligands in Catalysis

Synthesis and a combined experimental/theoretical structural study of a comprehensive set of Pd/NHC complexes witho-,m-, andp-halogen-substituted aryl groups (X = F, Cl, Br, CF3)

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Synthesis and a combined experimental/theoretical structural study of a comprehensive set of Pd/NHC complexes witho-,m-, andp-halogen-substituted aryl groups (X = F, Cl, Br, CF₃)