25364-47-0

Upstream product

• 25372-38-7 2-mercapto-1-(2,6-diisopropylphenyl)imidazole 
• 288-32-4 1H-imidazole 
• 163704-47-0 2-iodo-1,3-diisopropylbenzene 
• 57190-17-7 2-bromo-1,3-diisopropylbenzene 
• 50-00-0 formaldehyd 
• 131543-46-9 Glyoxal 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 67-56-1 methanol 
• 950677-69-7 1-(2,2-diethoxy-ethyl)-3-(2,6-diisopropyl-phenyl)-thiourea 
• 25343-70-8 2,6-diisopropylphenyl isothiocyanate 

Downstream Products

• 330455-93-1 [3-(2,6-diisopropylphenyl)-1-(2-pyridyl)imidazolium] bromide 
• 684261-42-5 1-[(S)-4-tert-butyl-4,5-dihydrooxazol-2-yl]-3-(2,6-diisopropylphenyl)imidazolium bromide 
• 873300-28-8 3-(2,6-diisopropylphenyl)-1-(2-oxo-2-phenylethyl)imidazolium bromide 
• 852057-21-7 1-(2,6-diisopropylphenyl)-3-methyl imidazolium iodide 
• 1003570-22-6 3-benzyl-1-(2,6-diisopropylphenyl)-1H-imidazol-3-ium bromide 

Relevant academic research and scientific papers

A magnetically separable palladium catalyst containing a bulky N-heterocyclic carbene ligand for the Suzuki-Miyaura reaction

This work describes the preparation and characterization of a magnetic palladium catalyst with bulky N-heterocyclic carbene (NHC) ligands for the Suzuki-Miyaura cross-coupling reaction. After the 1-(2,6-diisopropylphenyl)-1H-imidazole (1-arylimidazole) was modified on the surface of magnetic polymer carriers, palladium diacetate was employed to synthesize the Pd-NHC complex, affording a palladium loading of 0.23 mmol g?1. This magnetic catalyst showed high catalytic activity towards the Suzuki-Miyaura reaction of phenylboronic acids with aryl bromides in the ethanol-water solution (TON > 87 000). After 21 cycling runs, its catalytic activity decreased slightly, and no leaking of palladium was found either in products or in reaction residue. When other sources of palladium (PdCl2 and 3-Cl-pyridi-nyl) were employed to synthesize the palladium complex, the stability of the magnetic catalyst was greatly improved to perform the catalysis of Suzuki-Miyaura reactions with aryl chlorides at 100 °C.

Novel N-heterocyclic carbene cyclic palladium compound as well as preparation method and application thereof

The invention discloses a novel N-heterocyclic carbene cyclic palladium compound as well as a preparation method and application thereof, and belongs to the technical field of organic catalysis. The novel N-heterocyclic carbene cyclic palladium compound is prepared by the following steps: heating, stirring and mixing N-(4-butoxybenzyl)-N-ethylethylamine, palladium chloride and an organic solvent in an inert gas atmosphere, then adding potassium carbonate, performing stirring and mixing, and finally adding 1-(2,6-diisopropyl phenyl)-3-butyl-brominated imidazole for reflux reaction; and after the reaction is finished, performing quenching with an acid solution, performing extracting to obtain a crude product, and performing column chromatography separation and purification to obtain the novel N-heterocyclic carbene cyclic palladium compound. The N-heterocyclic carbene cyclic palladium compound provided by the invention has high catalytic activity, can catalyze cross-coupling reactions between aryl chloride and aryl phenylboronic acid and between aryl chloride and secondary amine in a catalytic amount of 1 mol%, and can be used as a high-efficiency catalyst for the coupling reactions.

Chiral-at-Iron Catalyst for Highly Enantioselective and Diastereoselective Hetero-Diels-Alder Reaction

This study demonstrates that chiral-at-iron complexes, in which all coordinated ligands are achiral and the overall chirality the consequence of a stereogenic iron center, are capable of catalyzing asymmetric transformations with very high enantioselectivities. The catalyst is based on a previously reported design (J. Am. Chem. Soc. 2017, 139, 4322), in which iron(II) is surrounded by two configurationally inert achiral bidentate N-(2-pyridyl)-substituted N-heterocyclic carbenes in a C2-symmetric fashion and complemented by two labile acetonitriles. By replacing mesityl with more bulky 2,6-diisopropylphenyl substituents at the NHC ligands, the steric hindrance at the catalytic site was increased, thereby providing a markedly improved asymmetric induction. The new chiral-at-iron catalyst was applied to the inverse electron demand hetero-Diels-Alder reaction between β,γ-unsaturated α-ketoester and enol ethers provide 3,4-dihydro-2H-pyrans in high yields with excellent diastereoselectivities (up to 99 : 1 dr) and excellent enantioselectivities (up to 98 % ee). Other electron rich dienophiles are also suitable as demonstrated for a reaction with a vinyl azide.

Synergy between supported ionic liquid-like phases and immobilized palladium N-heterocyclic carbene–phosphine complexes for the Negishi reaction under flow conditions

The combination of supported ionic liquids and immobilized NHC–Pd–RuPhos led to active and more stable systems for the Negishi reaction under continuous flow conditions than those solely based on NHC–Pd–RuPhos. The fine tuning of the NHC–Pd catalyst and the SILLPs is a key factor for the optimization of the release and catch mechanism leading to a catalytic system easily recoverable and reusable for a large number of catalytic cycles enhancing the long-term catalytic performance.

NHC copper complexes functionalized with sulfoxide and sulfone moieties

A series of N-heterocyclic copper carbene complexes bearing sulfoxide and sulfone moieties have been prepared. In case of new copper compounds with sulfone ligand, the solid-state structures were determined using X-Ray crystallography. Obtained complexes

Palladium-Catalyzed Methylation of Nitroarenes with Methanol

A procedure for the synthesis of N-methyl-arylamines directly from nitroarenes using methanol as green methylating agent was developed. The key to success is the use of a specific catalyst system consisting of palladium acetate and the ligand 1-[2,6-bis(isopropyl)phenyl]-2-[tert-butyl(2-pyridinyl)phosphino]-1H-Imidazole (L1). The generality of this protocol is demonstrated in the synthesis of more than 20 N-methyl-arylamines under comparably mild conditions. Combining this novel methodology with subsequent coupling processes using the same catalyst allows for efficient diversification of aromatic nitro compounds to a broad variety of amines including drug molecules.

Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents

The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bis-NHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.

Synthesis, Structural Characterization and Catalytic Activities of Sulfur-Functionalized NHC–Copper(I) Complexes

The synthesis of a family of N-heterocyclic carbene–copper complexes bearing a sulfur moiety by using different copper(I) halides through convenient procedures is reported. The solid-state structures of the presented copper compounds were elucidated based

Recyclable and eco-friendly Pd-complexed graphene oxide/N-heterocyclic carbene catalyst for various coupling reactions in aqueous phase

In this study, we report recyclable Pd-complexed graphene oxide (GO) catalysts with a bulky N-heterocyclic carbene (NHC) ligand (GO/NHC-Pd) for various cross-coupling reactions in the aqueous phase. To prepare GO/NHC-Pd, the NHC precursor and a trimethoxy-silane linker were combined on the GO surface via condensation, followed by the Pd chelation over GO/NHC. The GO-based catalysts were applied to three types of C–C cross-coupling reactions including Suzuki, Heck and Sonogashira reactions in the aqueous phase, to evaluate their catalytic performance. The reusability of the catalysts was tested by performing five consequent cross-coupling reactions.

Synthesis of xylylene-bridged dipalladium complexes with imidazole and triazole-based di-N-heterocyclic carbene (NHC) ligands

The di-N-heterocyclic carbene (NHC) dipalladium complexes, [(PdPyBr2)2(di-NHCimi)] and [(PdPyBr2)2(di-NHCtri)], di-NHCimi and di-NHCtri represent an imidazolylidene and a triazolylidene, respectively, featuring a 1,4-xylylene spacer between the carbene units, have been prepared. The influences of the imidazolylidene and triazolidene backbone and different substituents on the catalytic activity have been investigated in the Mizoroki-Heck reaction of styrene with bromobenzene.