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Relevant academic research and scientific papers

Ionic Pd/NHC Catalytic System Enables Recoverable Homogeneous Catalysis: Mechanistic Study and Application in the Mizoroki–Heck Reaction

N-Heterocyclic carbene (NHC) ligands are ubiquitously utilized in catalysis. A common catalyst design model assumes strong M–NHC binding in this metal–ligand framework. In contrast to this common assumption, we demonstrate here that lability and controlled cleavage of the M?NHC bond (rather than its stabilization) could be more important for high-performance catalysis at low catalyst concentrations. The present study reveals a dynamic stabilization mechanism with labile metal–NHC binding and [PdX3]?[NHC-R]+ ion pair formation. Access to reactive anionic palladium intermediates formed by dissociation of the NHC ligands and plausible stabilization of the molecular catalyst in solution by interaction with the [NHC-R]+ azolium ion is of particular importance for an efficient and recyclable catalyst. These ionic Pd/NHC complexes allowed for the first time the recycling of the complex in a well-defined form with isolation at each cycle. Computational investigation of the reaction mechanism confirms a facile formation of NHC-free anionic Pd in polar media through either Ph–NHC coupling or reversible H–NHC coupling. The present study formulates novel ideas for M/NHC catalyst design.

Highly efficient and green esterification of carboxylic acids in deep eutectic solvents without any other additives

A protocol that carboxylic acids esterifies with the quaternary ammonium salt of deep eutectic solvent (DES) is presented, which opens a new access to ester using DES as alkylating agent, solvent, and catalyst. The reaction runs smoothly in DES without any other additives. Substituted cinnamic acids, aromatic acids, and aliphatic acids can be esterified in moderate to good yields. The advantages of this reaction include excellent functional group compatibility and simple reaction procedure.

A Convoluted Polymeric Imidazole Palladium Catalyst: Structural Elucidation and Investigation of the Driving Force for the Efficient Mizoroki-Heck Reaction

MPPI-Pd (7 mol ppm Pd), prepared from poly(N-isopropylacrylamide-co-N-vinylimidazole) and (NH4)2PdCl4 by our molecular convolution method, promoted the Mizoroki-Heck reaction in water to give the corresponding coupling pro

Pyridinyl functionalized MCM-48 supported highly active heterogeneous palladium catalyst for cross-coupling reactions

An MCM-48 supported 2-pyridinylmethanimine Pd-catalyst was found to be a highly efficient catalyst in the Mizoroki-Heck, Suzuki-Miyaura and copper-free Sonogashira cross-coupling reactions of aryl halides under aqueous reaction conditions. The catalyst efficiently promoted these coupling reactions with ppm levels of palladium to afford the corresponding coupling products in up to 98% yield. The supported Pd-catalyst was readily recovered and reused several times without significant loss of its catalytic activity. This journal is

6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl]: A new ligand for palladium-catalyzed Mizoroki-Heck coupling

A novel and conveniently prepared diphosphine ligand 6H-Dibenzo[d,f-[1,3] diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl] (DADPP) combined with [Pd(C3H5)Cl]2 affords an efficient catalytic system for Mizoroki-Heck cross-coupling of aryl halides with alkenes. The system could give the yield of 95% for 4-chloronitrobenzene with 0.05 mol.% [Pd(C 3H5)Cl]2. For the bromide-substituted substrates, the highest turnover number (TON) is up to 96,000,000.

6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl]: A new ligand for palladium-catalyzed Mizoroki-Heck coupling

A novel and conveniently prepared diphosphine ligand 6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl] (DADPP) combined with [Pd(C3H5)Cl]2affords an efficient catalytic system for Mizoroki-Heck cross-coupling of aryl halides with alkenes. The system could give the yield of 95% for 4-chloronitrobenzene with 0.05 mol.% [Pd(C3H5)Cl]2. For the bromide-substituted substrates, the highest turnover number (TON) is up to 96,000,000.

Flow heck reactions using extremely low loadings of phosphine-free palladium acetate

High-yielding Heck reactions are demonstrated using 0.05 mol % Pd(OAc) 2 without phosphine ligands. These reactions are run in a mesoscale flow reactor which allows precise control of reaction times and temperatures. Profiling yield and selecti

A colorimetric high-throughput screening method for palladium-catalyzed coupling reactions of aryl iodides using a gold nanoparticle-based iodide-selective probe

Catching the couplings: A general and simple screening method for palladium-catalyzed coupling reactions of aryl iodides utilizes gold nanoparticles. This assay was successfully employed in several aminations, α-arylation of ketones, and decarboxylative couplings. 96 samples were screened in a few minutes. Copyright

Palladium-catalyzed Mizoroki-Heck coupling reactions using sterically bulky phosphite ligand

A new catalytic system based on palladium-phosphite for Mizoroki-Heck coupling reactions of aryl iodide and bromide is described. An air-stable phosphite ligand afforded the desired products with high yields in the palladium-catalyzed Mizoroki-Heck reacti

A lutidine-bridged bis-perimidinium salt: Synthesis and application as a precursor in palladium-catalyzed cross-coupling reactions

A novel lutidine-bridged bis-perimidini-um dibromide 3 was synthesized in quantitative yield from cheap commercial starting materials. The bisylidene prepared therefrom in situ upon deproto-nation is a potent precatalyst in palladium-catalyzed Heck and Suzuki cross-coupling reactions under aerobic conditions, and is efficient even with a ppm scale catalyst loading. Its stronger o-donor character is held to be responsible for its superior catalytic performance compared with imidazole- and benz-imidazole-based analogues bearing the same skeleton precursors.