47019-30-7

Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 619-44-3 methyl 4-iodobenzoate 
• 1571-08-0 methyl 4-formylbenzoate 
• 186581-53-3 diazomethane 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 624-31-7 4-tolyl iodide 
• 292638-85-8 acrylic acid methyl ester 
• 106918-31-4 1-methoxy-2-(4-carbomethoxyphenyl)ethylene 
• 380481-66-3 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane 
• 1076-96-6 methyl 4-vinylbenzoate 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 

Downstream Products

• 89165-05-9 1-(4-(hydroxymethyl)phenyl)-2-(4-methylphenyl)ethane 

Relevant academic research and scientific papers

Pd/Cu-catalyzed facile approach to stilbenes: A novel diversity of TosMIC as an aryl source

Pd/Cu-catalyzed Heck type cross-coupling reaction of p-toluenesulfonylmethyl isocyanide (TosMIC) with various styrenes to access stilbenes in DMSO solvent under mild conditions is developed. This efficient and simple approach employs TosMIC as an aryl sou

Highly E-Selective, Stereoconvergent Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkenyl Ethers

An improved method for the nickel-catalyzed Suzuki-Miyaura cross-coupling of alkenyl ethers is reported. This stereoconvergent protocol allows for the utilization of a wide range of alkenyl ethers and aryl boronic esters for the synthesis of variously sub

Catalytic Transfer Hydrogenation Using Biomass as Hydrogen Source

We developed an operationally simple method for the direct use of biomass-derived chemical entities in a fundamentally important process, such as hydrogenation. Various carbohydrates, starch, and lignin were used for stereoselective hydrogenation. Employing a transition metal catalyst and a novel catalytic system, the reduction of alkynes, alkenes, and carbonyl groups with high yields was demonstrated. The regioselective hydrogenation to access different stereoisomers was established by simple variations in the reaction conditions. This work is based on an unprecedented catalytic system and represents a straightforward application of biomass as a reducing reagent in chemical reactions.

Iodine-catalysed transfer hydrogenation of a carbon-carbon σ-bond with water

Iodine catalysed the transfer hydrogenation of a benzylic C-C σ-bond in [2.2]paracyclophane with water to yield 4,4′-dimethylbibenzyl. The C-C σ-bond was first cleaved by homolytic substitution with iodine radicals to produce a 4,4′-diiodomethylbibenzyl i

Kryptofix 5 as an inexpensive and efficient ligand for the palladium-catalyzed Mizoroki-Heck reaction

A novel complex of PdCl2 with a multidentate cryptand ligand, Kryptofix 5, has been prepared and characterized by various techniques including 1H- and 13C NMR spectroscopy, Fourier transform infrared (FT-IR), Raman, ultraviolet and visible (UV-VIS) spectroscopy, inductively coupled plasma (ICP), CHN elemental and energy dispersive X-ray analysis (EDX). This heat- and air-stable complex was utilized as a highly active catalyst for the Mizoroki-Heck reaction of aryl halides with various olefins. Interestingly, it was found that aryl bromides as well as aryl iodides were efficiently cross-coupled with terminal alkenes at 130?°C in 10?min. Furthermore, the least reactive aryl chlorides reacted with styrene to obtain the desired products in acceptable yields.

Chemoselective and Sequential Palladium-Catalyzed Couplings for the Generation of Stilbene Libraries via Immobilized Substrates

A versatile palladium-catalyzed tandem synthetic sequence to afford E-stilbenes libraries has been developed. Excellent regio- and stereocontrol have been achieved by means of the sequence of Hiyama and Heck cross-couplings. Undesirable homocoupling bypro

Rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes

A rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes to afford 1,2-disubstituted alkenes with good regio- and E-selectivity is developed. This reaction employs readily available aromatic aldehydes as the aryl electrophile counterpart and relies on selected acyl chloride as the crucial additive to activate the rhodium catalyst precursor.

Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts

Palladium (10 wt%) on a highly cross-linked imidazolium-based material was used as catalyst in 0.1 mol% in the Heck reaction between several alkenes and aryl iodides. Products were obtained from good to high yields. Deeper investigations showed a release of Pd species in solution and their capture by the imidazolium-based support. When a sixfold amount of support was employed the re-captured Pd species (0.5-0.6 wt%) were not anymore catalytically active. This result represents a new interesting aspect of this work since the highly cross-linked imidazolium-based material can act also as Pd scavenger avoiding the release of the metal in solution. Important differences between Heck and Suzuki reactions have been evidenced when the reactions were carried out in the presence of the scavenging support.

Unravelling the olefin cross metathesis on solid support. Factors affecting the reaction outcome

Olefin cross metathesis on solid support under a variety of conditions is described. A comprehensive analysis considering diverse factors governing the reaction outcome gives a series of patterns for the application of this useful methodology in organic synthesis. If the intrasite reaction is not possible, homodimerization of the soluble olefin is crucial. When the homodimer is less reactive than its monomer, reaction outcome depends on the homodimerization rate, which, in turn, depends on the precatalyst used and the reaction conditions. If the site-site interaction is a feasible process, the cross metathesis product is obtained exclusively when the newly-formed double bond is resilient to further metathetic events. Taking into account these considerations, we have demonstrated that excellent results in terms of cross metathesis coupling can be obtained under the optimized conditions, and that microwave irradiation is also an interesting alternative for the development of a practical and energy-efficient cross metathesis on solid support.

Nickel-catalyzed cross-coupling reaction of alkenyl methyl ethers with aryl boronic esters

The Ni(0)-catalyzed cross-coupling of alkenyl methyl ethers with boronic esters is described. Several types of alkenyl methyl ethers can be coupled with a wide range of boronic esters to give the stilbene derivatives.