38695-40-8

Upstream product

• 352-34-1 4-fluoro-1-iodobenzene 
• 1866-39-3 trans-p-methylcinnamic acid 
• 624-31-7 4-tolyl iodide 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 405-99-2 para-fluorostyrene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 96783-59-4 1-(4-fluorophenyl)-2-(pyrrolidin-1-yl)diazene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 90252-89-4 p-tolylzinc(II) chloride 
• 3762-25-2 diethyl 4-methylbenzylphosphonate 
• 459-57-4 4-fluorobenzaldehyde 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 64583-47-7 1‐fluoro‐4‐(4‐methylphenethyl)benzene 

Relevant academic research and scientific papers

Lipids as versatile solvents for chemical synthesis

Development of safe, renewable, cheap and versatile solvents is a longstanding challenge in chemistry. We show here that vegetable oils and related systems can become prominent solvents for organic synthesis. Suzuki-Miyaura, Hiyama, Stille, Sonogashira and Heck cross-couplings proceed with quantitative yields in a range of vegetable oils, fish oil, butter and waxes used as solvents. Appropriate methodologies for high-throughput screening and sustainable isolation techniques applicable for vegetable oils and related lipids are presented.

Palladium-Catalyzed Mizoroki-Heck Reaction of Nitroarenes and Styrene Derivatives

We have developed a Mizoroki-Heck reaction of nitroarenes with alkenes under palladium catalysis. The use of a Pd/BrettPhos catalyst promoted the alkenylation, whereas other catalysts led to a decrease in the product yield. In addition to nitroarenes, nitroheteroarenes were also applicable to the present reaction. The combination of a nucleophilic aromatic substitution (SNAr) with the denitrative alkenylation produced a multifunctionalized arene in a one-pot operation.

Decarboxylative Arylation of α,β-Unsaturated Carboxylic Acids Using Aryl Triazenes by Copper/Ionic Liquid Combination in PEG-400

A practical method for the construction of stilbene derivatives has been developed via catalytic cross-coupling of cinnamic acids with aryl triazenes. The methodology offers high stereoselectivity and is endowed with broad substrate scope, high yield, and significant functional group tolerance.

An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence

An interrupted Pummerer/nickel-catalysed cross-coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one-pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp-, sp2-, and sp3-hybridised organozinc coupling partners, and delivers functionalised styrene products in high yields over two steps. An interrupted Pummerer/cyclisation approach has also been used to access carbo- and heterocyclic alkenyl sulfonium salts for cross-coupling.

Activation of anti-oxidant Nrf2 signaling by substituted trans stilbenes

Nrf2, which is a member of the cap'n’ collar family of transcription factors, is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. The importance of inflammation and oxidative stress in many chronic diseases supports the concept that activation of anti-oxidant Nrf2 signaling may have therapeutic potential. A number of Nrf2 activators have entered into clinical trials. Nrf2 exists in the cytosol in complex with its binding partner Keap1, which is a thiol-rich redox-sensing protein. In response to oxidative and electrophilic stress, select cysteine residues of Keap1 are modified, which locks Keap1 in the Nrf2-Keap1 complex and allows newly synthesized Nrf2 to enter the nucleus. Numerous Nrf2-activating chemicals, including a number of natural products, are electrophiles that modify Keap1, often by Michael addition, leading to activation of Nrf2. One concern with the design of Nrf2 activators that are electrophilic covalent modifiers of Keap1 is the issue of selectivity. In the present study, substituted trans stilbenes were identified as activators of Nrf2. These activators of Nrf2 are not highly electrophilic and therefore are unlikely to activate Nrf2 through covalent modification of Keap1. Dose-response studies demonstrated that a range of substituents on either ring of the trans stilbenes, especially fluorine and methoxy substituents, influenced not only the sensitivity to activation, reflected in EC50values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2. The stilbene backbone appears to be a privileged scaffold for development of a new class of Nrf2 activators.

Mono- and multifold C-C coupling reactions catalyzed by a palladium complex encapsulated in MIL-Cr as a three dimensional nano reactor

The organic palladium complex (trans-dichlorobis(4-iodoaniline-κN)palladium(ii)) was encapsulated into a porous metal-organic framework MIL-Cr (Pd complex@MIL-Cr) using ship-in-a-bottle strategy. The novel catalyst as a three dimensional nanoreactor was fully characterized using different techniques such as XRD, BET, XPS, SEM, EDX, TEM and ICP. The Pd complex@MIL-Cr is isostructural to the parent MIL-Cr framework, with a high surface area and pore volume of ca. 1418 m2 g-1 and 0.87 cm3 g-1, respectively. The nanoreactor was highly efficient in the catalytic conversion of aryl halides, showing extraordinarily higher activity than the homogeneous Pd counterparts. Surprisingly, high yields were achieved in Suzuki-Miyaura and Heck coupling reactions of chloroarenes bearing a wide range of substituents. Besides, this protocol could be extended to the cross-couplings of 2-bromo and 2,6-dibromopyridine with arylboronic acids in excellent yields at room temperature. The Pd complex@MIL-Cr was also used as an efficient and convenient catalyst for the preparation of a series of C3-symmetric molecules with benzene, pyridine or pyrimidine units as the central core. Moreover, the catalyst could be recovered easily and reused several times without any considerable loss of its catalytic activity. Investigation of the nature of the recovered catalyst showed that the catalyst is converted to Pd nanoparticles.

Novel polymer supported iminopyridylphosphine palladium (∥) complexes: An efficient catalyst for Suzuki-Miyaura and Heck cross-coupling reactions

A novel cross-linked polyallylamine polymer supported iminopyridylphosphine palladium∥ complexes have been prepared and shown to be highly efficient catalysts for Suzuki-Miyaura and Heck cross-coupling reactions under low Pd loading (0.05% mol). Remarkably, the catalyst can be recycled and reused without loss of catalytic activity through simple filtration.

Aerobic palladium-catalyzed arylation of alkenes using sodium sulfinates

Palladium-catalyzed oxidative arylations of terminal alkenes could be performed using sodium sulfinates at 60 °C in air. The procedure gave various aryl alkenes after the desulfonylation of sodium arylsulfinates in the presence of a palladium catalyst. For instance, the reaction of styrene with sodium phenylsulfinate afforded trans-1,2-diphenylethylene in 80% yield without the formation of other stereoisomers. Georg Thieme Verlag Stuttgart · New York.

Palladium nanoparticles immobilized on nano-silica triazine dendritic polymer (Pdnp-nSTDP): An efficient and reusable catalyst for suzuki-miyaura cross-coupling and heck reactions

A new catalyst based on palladium nanoparticles immobilized on nano-silica triazine dendritic polymer (Pdnp-nSTDP) was synthesized and characterized by FT-IR spectroscopy, thermogravimetric analysis, field emission scanning electron microscopy, energy dispersive X-ray, transmission electron microscopy and elemental analysis. The size of the palladium nanoparticles was determined to be 3.1±0.5 nm. This catalytic system showed high activity in the Suzuki-Miyaura cross-coupling of aryl iodides, bromides and chlorides with arylboronic acids and also in the Heck reaction of these aryl halides with styrenes. These reactions were best performed in a dimethylformamide (DMF)/water mixture (1:3) in the presence of only 0.006 mol% and 0.01 mol% of the catalyst, respectively, under conventional conditions and microwave irradiation to afford the desired coupling products in high yields. The Pdnp-nSTDP was also used as an efficient catalyst for the preparation of a series of star- and banana-shaped compounds with a benzene, pyridine, pyrimidine or 1,3,5-triazine unit as the central core. Moreover, the catalyst could be recovered easily and reused several times without any considerable loss of its catalytic activity. Copyright

Sodium sulfinate-mediated trans-stilbene formation from benzylic halides

A convenient and efficient method for the synthesis of various symmetrical and non-symmetrical trans-stilbene derivatives from benzylic halides in the absence of any transition metals is described. Sodium sulfinates played an important role in this transformation. Various functional groups were well tolerated under the optimized reaction conditions. Copyright