17024-58-7

Upstream product

• 100-42-5 styrene 
• 480-63-7 mesitylenecarboxylic acid 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 5350-76-5 1-phenyl-2-(2,4,6-trimethylphenyl)ethanone 
• 4747-15-3 1-(2-methoxyvinyl)benzene 
• 2633-66-1 2-mesitylmagnesium bromide 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 100-52-7 benzaldehyde 
• 4110-75-2 (E)-(2-methoxyvinyl)benzene 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 769-25-5 2,4,6-trimethylstyrene 
• 66003-76-7 Diphenyliodonium triflate 
• 108-67-8 1,3,5-trimethyl-benzene 

Downstream Products

• 16664-45-2 1,3-dimethylphenanthrene 
• 858807-62-2 2-mesityl-3-phenyl-succinic acid 
• 143425-74-5 1-(2',4',6'-trimethylphenyl)-2-phenylethane 
• 20488-50-0 (Z)-1,3,5-trimethyl-2-(2-phenylethenyl)benzene 
• 480-63-7 mesitylenecarboxylic acid 
• 149603-31-6 1-phenyl-2-mesityl-ethanediol-(1,2) 
• 527-60-6 Mesitol 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Rapid room temperature buchwald-hartwig and suzuki-miyaura couplings of heteroaromatic compounds employing low catalyst loadings

The use of second-generation [(NHC)Pd(R-allyl)Cl] complexes for Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions involving heteroaromatic halides at room temperature is reported. The first examples of room temperature Suzuki-Miyaura cross-coupling of deactivated aryl chlorides with alkenyl boronic acids are also disclosed. Terminal substitution at the allyl moiety of the palladium complex facilitates its activation at room temperature leading to very active catalytic species enabling the present catalytic transformations to be performed rapidly using very mild reaction conditions. Catalyst loadings can be as low as 10 ppm for the Buchwald-Hartwig aryl amination and 50 ppm for the Suzuki-Miyaura reaction.

METHODS OF ARENE ALKENYLATION

The present disclosure provides for a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. For example, the present disclosure provides for method of making arenes or substituted arenes, in particular stilbene and stilbene derivatives, from a reaction of an optionally substituted arene and/or optionally substituted styrene. The reaction includes a Rh catalyst or Rh pre-catalyst material and an oxidant, where the Rh catalyst or Rh catalyst formed Rh pre-catalyst material selectively functionalizes CH bond on the arene compound (e.g., benzene or substituted benzene).

Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation

Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we report a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. The reaction is successful with several functional groups on both the arene and the olefin including fluoride, chloride, trifluoromethyl, ester, nitro, acetate, cyanide, and ether groups. Reactions of monosubstituted arenes are selective for alkenylation at the meta and para positions, generally with approximately 2:1 selectivity, respectively. Resveratrol and (E)-1,2,3-trimethoxy-5-(4-methoxystyryl)benzene (DMU-212) are synthesized by this single-step approach in high yield. Comparison with palladium catalysis showed that rhodium catalysis is more selective for meta-functionalization for monosubstituted arenes and that the Rh catalysis has better tolerance of halogen groups.

Carbonyl–Olefin Cross-Metathesis Through a Visible-Light-Induced 1,3-Diol Formation and Fragmentation Sequence

A visible-light-mediated approach to carbonyl–olefin cross-metathesis is described. Photoinduced hole catalysis was used to promote the formation of 1,3-diols from aldehydes and styrenes, which were then readily fragmented under acidic conditions to form the cross-metathesis products. The use of 1,3-diols as intermediates, rather than the energetically more demanding oxetanes, provides a new, orthogonal mechanistic strategy for carbonyl–olefin cross-metathesis. Furthermore, this approach does not require any metals, ligands, or additives, and provides the products with high levels of E selectivity. A mechanistic rationale is provided and supported by both theoretical calculations and experiments. Additionally, a practical synthesis of a new acridinium-based photocatalyst, including full characterization, is presented.

Nickel-Catalyzed system for the cross-coupling of alkenyl methyl ethers with grignard reagents under mild conditions

A nickel-catalyzed cross-coupling of alkenyl methyl ethers with Grignard reagents, under mild conditions, is described. These conditions allowed access to various stilbenes and heterocyclic stilbenic derivatives as well as to a potential anticancer agent DMU-212.

Synthesis and Characterization of C, C -Type Palladacycles and Their Catalytic Application in Mizoroki-Heck Coupling Reaction

Two series of ligand precursors, based on imidazo[1,2-a]pyridine and C2-phenyl substituted imidazole moieties, were developed and synthesized in high yields, featuring an N-CH2(C=O)Ar substituent on the imidazole ring. Upon reacting with palladium acetate, both series of ligands underwent double C-H bond activations at the methylene and o-aryl carbon sites on the N-CH2(C=O)Ar substituent, yielding C,C-type palladacycles bearing five-membered chelate rings. A dimeric palladium complex with bridging bromides was obtained from the ligand precursor with the bromide anion, whereas an ionic palladium complex with two "throw away" pyridine ligands was formed with the precursor of the tetrafluoroborate anion. All complexes are air-stable and were characterized by 1H and 13C NMR spectroscopy and elemental analysis. The structures of three of the new complexes were further established by single-crystal X-ray diffraction studies. These complexes have been screened for catalyzing Mizoroki-Heck coupling reaction using ionic salt as solvent. The complex based on imidazo[1,2-a]pyridine, which has an electron-donating 4-methoxyphenyl ring on the ligand scaffold, was the most efficient catalyst, capable of using activated aryl chloride and sterically hindered aryl bromide as substrates. It was also successfully applied in the green process of one-pot Mizoroki-Heck coupling/trans-esterification reaction in molten ionic salt.

Cyclodextrin-Grafted Silica-Supported Pd Nanoparticles: An Efficient and Versatile Catalyst for Ligand-Free C-C Coupling and Hydrogenation

Silica is an extremely versatile support, which is capable of hosting metal nanoparticles (NPs) and enhancing their stability and reactivity. In this study, a novel cyclodextrin/silica support for Pd NPs, which we have denoted Pd/Si-CD, has been prepared. The highly efficient and homogeneous impregnation of small palladium nanoparticles on this support has been carried out under conventional conditions, and ultrasound irradiation has been shown to have a beneficial effect on catalyst preparation. The catalyst exhibited excellent activity in ligand-free C-C Suzuki and Heck couplings with a large number of aryl iodide and bromides, in which microwave irradiation use cuts down reaction time. Pd/Si-CD have shown high activity and selectivity in the hydrogenation reaction, and the semihydrogenation of phenyl acetylene was also studied with excellent results.

THERAPEUTIC AGENTS FOR SKIN DISEASES AND CONDITIONS

The present invention relates to method(s) of treating a subject afflicted with a skin disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans- stilbene or a stilbene hybrid. A method of treating or reducing the likelihood of a skin disease or condition in a patient is an additional embodiment of the present invention. Preferred pharmaceutical compositions of the invention include nanoemulsions comprising a therapeutically effective amount of a substituted cis or trans-stilbene or stilbene hybrid and at least one antibiotic.

Microwave-assisted palladium-catalyzed arylation of styrenes and alkenes with diaryliodonium salts

Highly effective microwave-assisted palladium-catalyzed arylation of styrenes and alkenes with diaryliodonium salts have been developed, giving styrenes in high yields without ligand in 60 s.

Oxidative Mizoroki-Heck-type reaction of arylsulfonyl hydrazides for a highly regio- and stereoselective synthesis of polysubstituted alkenes

A useful source: Arylsulfonyl hydrazides have been identified as synthetically useful aryl sources for the Pd(OAc)2 catalyzed oxidative Mizoroki-Heck-type reaction under molecular oxygen to provide a convenient access to polysubstituted alkenes in a highly regio- and stereoselective manner (see scheme). The reaction well tolerates various functional groups such as alkoxy, halo, alcohol, carboxylic acid, ester, amide, sulfonamide, and sulfone. Copyright