23746-55-6

Upstream product

• 624-38-4 para-diiodobenzene 
• 292638-85-8 acrylic acid methyl ester 
• 608-74-2 hexaiodobenzene 
• 1779-58-4 (methyloxycarbonylmethyl)triphenylphosphonium bromide 
• 623-27-8 terephthalaldehyde, 
• 106-50-3 1,4-phenylenediamine 
• 106-37-6 1.4-dibromobenzene 
• 67-56-1 methanol 
• 89129-23-7 3,3'-(1,4-phenylene)bis[2-propenoyl chloride] 
• 589-87-7 1,4-bromoiodobenzene 
• 105-06-6 1,4-Divinylbenzene 
• 201230-82-2 carbon monoxide 
• 636-31-7 1,2,4,5-tetraiodobenzene 
• 23713-85-1 1,4-phenylenediacrylic acid 

Downstream Products

• 5312-03-8 dimethyl 3,3'-(1,4-phenylene)dipropanoate 

Relevant academic research and scientific papers

The role of symmetric functionalisation on photoisomerisation of a UV commercial chemical filter

Photoisomerisation has been shown to be an efficient excited-state relaxation mechanism for a variety of nature-based and artificial-based molecular systems. Here we report on the excited-state relaxation dynamics and consequent photostability of a symmet

High Loading of Pd Nanoparticles by Interior Functionalization of MOFs for Heterogeneous Catalysis

In this report, the issue related to nanoparticle (NP) agglomeration upon increasing their loading amount into metal-organic frameworks (MOFs) has been addressed by functionalization of MOFs with alkyne groups. The alkynophilicity of the Pd2+ (or other noble metals) ions has been utilized successfully for significant loading of Pd NPs into alkyne functionalized MOFs. It has been shown here that the size and loading amount of Pd NPs are highly dependent on the surface area and pore width of the MOFs. The loading amount of Pd NPs was increased monotonically without altering their size distribution on a particular MOF. Importantly, the distinct role of alkyne groups for Pd2+ stabilization has also been demonstrated by performing a control experiment considering a MOF without an alkyne moiety. The preparation of NPs involved two distinct steps viz. adsorption of metal ions inside MOFs and reduction of metal ions. Both of these steps were monitored by microscopic techniques. This report also demonstrates the applicability of Pd@MOF NPs as extremely efficient heterogeneous catalysts for Heck-coupling and hydrogenation reactions of aryl bromides or iodides and alkenes, respectively.

Preparation, properties, and structures of pentanuclear [{Ni2l}2(μ-csalen)M]2+ complexes (l = macrocyclic N6S2 donor ligand)

The dinuclear nickel complex [Ni2L(μ-Cl)]+ (1), where L2- is a 24-membered macrocyclic N6S2 ligand, reacts readily with 3-form-yl-4-hydroxy-benzoic acid (Hfhba) to form the carboxylato-bridged complex [Ni2L(μ-fhba)]+ (2). Complex 2 undergoes a condensation reaction with ethylene diamine to produce a tetranuclear complex [{Ni2L}2(μ-H2csalen)]2+ + (3), in which two dinuclear {Ni2L} units are bridged via the deprotonated carboxylate functions of the csalen ligand N,N′-bis(4-carboxysalicylidene)-1,2-diaminoethane. The same compound can also be prepared directly from 1 and H2csalen. The complexation of 3 with NiCl2?6H2O, Cu(OAc)2?H2O or Pd(OAc)2 provides pentanuclear complexes of the type [{Ni2L}2(μ-csalen)M]2+ [M = Ni (4a), Cu (4b), Pd (4c)]. All complexes were isolated as perchlorate salts and studied by ESI-MS, infrared, and UV/Vis spectroscopy. The tetraphenylborate salt of 4c was also characterized by X-ray crystallography. The [(csalen)M] complex units act in all cases as quadridentate bridging ligands linking two bioctahedral {Ni2L} units via μ-1,3-bridging carboxylate functions. The palladium complex 4c was found to catalyze Heck-coupling reactions of various iodobenzenes with methyl acrylate and styrene.

Palladium-catalyzed alkoxycarbonylation of terminal alkenes to produce α,β-unsaturated esters: The key role of acetonitrile as a ligand

A mild protocol has been developed for the PdII-catalyzed alkoxycarbonylation of terminal olefins to produce α,β-unsaturated esters with a wide range of substrates. Key features are the use of MeCN as solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O2, which facilitates the CuII-mediated reoxidation of the Pd0 complex to Pd II and prevents double carbonylation. Acetonitrile is the key! A mild protocol has been developed for the PdII-catalyzed alkoxycarbonylation of terminal olefins to produce α,β-unsaturated esters with a wide range of substrates (see scheme). Key features are the use of MeCN as a solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O2, which facilitates the CuII-mediated reoxidation of Pd0 to PdII and prevents double carbonylation.

Transition-metal-catalyzed chemoselective methylenation of dicarbonyl substrates

(Chemical Equation Presented) Rhodium- and copper-catalyzed methylenation reactions with trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol were used to react chemoselectively with aldehydes, alkoxymethylketones, and triftuoromethylketones in substrates also containing a less reactive carbonyl group. Terminal alkenes were obtained in high yields, and no protecting group was necessary in the methylenation process.

Oxidative demetalation of Fischer alkoxy carbene complexes with stoichiometric pyridine N-oxide and NaBH4-promoted demetalation of Fischer iminocarbene complexes with sulfur and selenium

Oxidation of Fischer alkoxy carbene complexes were systematically investigated with stoichiometric pyridine N-oxide (PNO) under mild conditions, forming ester products in good to excellent yields from the corresponding monocarbene complexes. Fischer alkoxy biscarbene complexes efficiently underwent stepwise oxidative demetalation under controlled conditions, resulting in ester-monocarbene and diester products, respectively. This oxidation protocol has demonstrated a generally efficient method to oxidize Fischer alkoxy carbene complexes under mild conditions, providing a new route to novel monocarbene complexes from Fischer biscarbene complexes. In the presence of NaBH4, reactions of Fischer iminocarbene complexes with elemental sulfur or selenium in ethanol at ambient temperature regioselectively afforded thione or selone complexes by insertion of a sulfur or selenium atom into the M{double bond, long}C bonds in Fischer carbene complexes, and metal-free selone was also obtained. The molecular structures of the iminocarbene complexes and selone derivatives were confirmed by X-ray crystallographic study. The NaBH4-promoted demetalation protocol suggests a potential new route to demetalate Fischer aminocarbene complexes.

Catalysis and regioselectivity of the aqueous Heck reaction by Pd(0) nanoparticles under ultrasonic irradiation

An aqueous Heck reaction carried out under ultrasonic irradiation at the ambient temperature (25 °C) has been shown in this study to afford high yields of corresponding products. It was found that as a catalyst for the reaction palladium forms nanoparticles in-situ, characterized by transmission electron microscopy (TEM) and X-ray powder diffraction (XRD) analyses, and can be recycled. Furthermore, the Heck reaction under such mild and environmentally friendly conditions offers excellent regioselectivity of para-over ortho-substitution in phenyl iodides especially with electron-donating groups.

Synthesis of a Novel C2-Symmetric Thiourea and Its Application in the Pd-Catalyzed Cross-Coupling Reactions with Arenediazonium Salts under Aerobic Conditions

(Matrix presented) A novel thiourea-based C2-symmetric ligand was synthesized, and its application in the palladium-catalyzed Heck and Suzuki coupling reactions of arenediazonium salts was evaluated. The reactions, which were performed at room temperature, without added base, and under aerobic conditions, produced product in 4 h with good yield. The corresponding arenediazonium salts were easily generated in one step from anilines.

Palladium-Catalyzed Alkenylation and Alkynylation of Polyhaloarenes

Alkenylation of several polyhaloarenes proceeded in low to moderate yields.Iodo groups could be reacted selectively in the presence of bromo groups; however, no more than two alkenyl groups could be introduced on contiguous, aromatic carbons.Alkynylation