88741-06-4

Upstream product

• 1868-53-7 dibromofluoromethane 
• 13189-30-5 1-phenylspiro<2.4>hepta-4,6-diene 
• 100-42-5 styrene 
• 456-48-4 3-Fluorobenzaldehyde 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 536-74-3 phenylacetylene 
• 29778-28-7 1-fluoro-3-(2-phenylethynyl)benzene 
• 350-51-6 3-fluorostyrene 
• 603-35-0 triphenylphosphine 
• 462-06-6 fluorobenzene 
• 108-86-1 bromobenzene 
• 403-54-3 m-Fluorobenzonitrile 
• 1073-06-9 3-fluorobromobenzene 
• 108-90-7 chlorobenzene 

Downstream Products

• 523-41-1 2-Fluor-phenanthren 
• 1346939-26-1 (E)-4-methyl-4′-styryl-1,1-biphenyl 

Relevant academic research and scientific papers

Electrochemical Proton Reduction over Nickel Foam for Z-Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes

Selective reduction strategies based on abundant-metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z-alkenes was developed, using a simple nickel foam as catalyst and H3O+ or D3O+ as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities (Z/E up to 20 : 1) were obtained under very mild reaction conditions. The reaction proceeded with terminal and nonterminal alkynes, and also with alkynes containing easily reducible functional groups, such as carbonyl groups, as well as aryl chlorides, bromides, and even iodides. The nickel-foam electrocatalyst could be recycled up to 14 times without any change in its catalytic properties.

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).

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Method for synthesizing trans-olefin compound

The invention discloses a trans-olefin compound synthesis method, which comprises: carrying out a heating reaction on an alkyne compound represented by a general formula (I), a reducing agent and a solvent to obtain a trans-olefin compound represented by a general formula (II), wherein the synthesis route is as follows: R1 and R2 are independently selected from hydrogen, alkyl, cycloalkyl or aryl;wherein the reducing agent is a sulfur-containing compound and is selected from at least one of thioacetamide, N,N-dimethyl dithiocarbamate dimethyl ammonium salt, dimethyl amino sodium dithioformatedihydrate, potassium ethyl xanthate and potassium isopropyl xanthate. According to the method, a cheap, efficient and safe reducing agent is utilized to realize high-selectivity reduction of alkyne to prepare trans-olefin under the condition of no transition metal catalysis, so that the method is simple and easy to implement, wide in substrate application range and easy to realize industrialization.

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.

Xanthate-mediated synthesis of (E)-alkenes by semi-hydrogenation of alkynes using water as the hydrogen donor

Semi-hydrogenation of alkynes is one of the most widely used methods for obtaining alkenes in laboratory preparation and in industry. Transition metal catalysts have been extensively studied for this transformation, but the tolerance of functional groups, such as pyridine,-OH,-NH2,-Bpin, and halides, and the toxicity of the trace amount of transition metal catalysts are still highly challenging. In this study, we report a general and robust strategy to achieve the semi-hydrogenation of alkynes using inexpensive and commercially available xanthate as the mediator. Mechanism studies support a non-radical process and H2O acts as the hydrogen donor.

Transition-Metal-Free Highly Chemoselective and Stereoselective Reduction with Se/DMF/H2O System

A novel metal-free reduction system, in which H2Se (or HSe-) produced in situ from Se/DMF/H2O acts as the active reducing species, has been developed. By using water as an inexpensive, safe, and environmentally friendly surrogate as the hydrogen donor, this new reduction system incorporating Se/DMF/H2O displayed high selectivity and good activity in the reduction of α,β-unsaturated ketones and alkynes. Therefore, this reduction system has great potential to be a general and practical reduction methodology in organic transformation.

Preparation method of trans-stilbene compound

The invention relates to a synthesis method of a trans-stilbene compound. In an atmosphere of nitrogen or inert gas and an organic solvent, diphenylacetylene serves as a reaction substrate, and the trans-stilbene compound is obtained through chemically se

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.

Ligand- and copper-free Sonogashira and Heck couplings of (Het)aryl chlorides and bromides catalyzed by palladium nanoparticles supported on in situ generated Al(OH)3

The ligand- and copper-free Sonogashira reaction of (Het)aryl halides (Br and Cl) with various terminal alkynes and the Heck coupling of (Het)aryl halides (Br and Cl) with a series of olefins, catalyzed by palladium nanoparticles supported on newly generated Al(OH)3, were developed. The catalyst can be readily recovered and reused 6 times without significant loss of activity and palladium leaching.