24840-11-7

Upstream product

• 100-42-5 styrene 
• 100-41-4 ethylbenzene 
• 4748-78-1 4-ethylbenzylaldehyde 
• 536-74-3 phenylacetylene 
• 29778-20-9 1-ethyl-4-(phenylethynyl)benzene 
• 100-52-7 benzaldehyde 
• 25309-64-2 4-ethyl-1-iodobenzene 
• 63139-21-9 4-ethylphenylboronic acid 
• 71-43-2 benzene 
• 103-80-0 phenylacetyl chloride 
• 24062-74-6 1-(4-ethylphenyl)-2-phenyl-1-ethanone 

Relevant academic research and scientific papers

Ready approach to poly(vinyldiphenylphosphine): A novel soluble polymer for conveniently conducting Wittig reactions

The novel poly(vinyldiphenylphosphine) could be easily prepared by using the reactions of the cheap poly(vinyl chloride) with sodium phosphides. Poly(vinyldiphenylphosphine) is soluble in common solvents while its corresponding phosphine oxide is hardly soluble in the solvents. Taking advantage of this different solubility, poly(vinyldiphenylphosphine) could be used as a soluble phosphinopolymer for the Wittig reactions. The reactions could take place efficiently to produce the corresponding olefins while the isolation of the products were simple since the resulted poly(vinyldiphenylphosphine oxide) was not soluble in the solvent and could be easily removed by filtration.

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.

Cobalt catalyzed stereodivergent semi-hydrogenation of alkynes using H2O as the hydrogen source

Cobalt-catalyzed stereodivergent semi-hydrogenation of internal alkynes to alkenes is developed. The reaction proceeded through transfer hydrogenation under mild conditions using a base metal CoI2 as the catalyst, and H2O/MeOH as the hydrogen source with Zn as the reductant. The E/Z-selectivity of the product could be switched by changing the solvent and by inclusion/exclusion of a bidentate phosphine ligand (dppe). This method provides a simple and cost effective pathway for the synthesis of 1,2-dideuterioalkenes.

Synthesis, characterization of palladium hydroxysalen complex and its application in the coupling reaction of arylboronic acids: Mizoroki-Heck type reaction and decarboxylative couplings

(Salen-OH)Pd (1, salen-OHN,N′-bis(3,5-di-hydroxysalicylidene)- ethylenediamine) was prepared by a simple one step reaction and fully characterized by 1H and 13C NMR, IR spectroscopy, and X-ray crystallography. This palladium complex showed good activities as a catalyst in the Mizoroki-Heck-type reaction and the decarboxylative coupling reaction. In the Mizoroki-Heck type reaction, arylboronic acids and alkenes were reacted at 90°C for 3 h in the presence of 2.0 mol% of the palladium complex 1 and AgOAc to give the desired coupled product in good yields. In the decarboxylative coupling reactions, the desired coupled products were obtained in good yields when 0.5 mol% of the palladium complex was employed at room temperature.

Effects of substituent and solvent on the UV absorption energy of 4,4′-disubstituted stilbenes

Twenty five samples of 4,4′-disubstituted stilbene derivatives were synthesized, and their UV absorption max wavelengths were determined in over 10 kinds of solvents including cyclohexane, ether, chloroform, acetonitrile and ethanol, in which 242 experimental data were recorded. The effects of substituents and solvents on the energy of their UV absorption max wavelengths were discussed. The research results showed: the energy of UV absorption max wavelengths of 4,4′-disubstituted stilbenes was mainly affected by their intramolecular structure (substituent effect) in a given solvent, that is, the energy is dominated by both of excited-state substituent parameter σ CC ex and polar substituent constant σ p. While their energy was dominated by the substituent effect and solvent effect in different kinds of solvents. An equation quantifying the energy of UV absorption max wavelengths of 4,4′-disubstituted stilbenes was developed. In addition, it is found that the n-octanol/water partition coefficient (logP) is more effective than the solvatochromic dye (E T(30)) in scaling the solvent effect. The equation employed the parameter logP has a better correlation and more specific physical meaning. Further, the energies of UV absorption max wavelengths of some reported compounds were predicted by the obtained equation, which are in agreement with their experimental values.

Efficient Aqueous-Phase Heck and Suzuki Couplings of Aryl Bromides Using Tri(4,6-dimethyl-3-sulfonatophenyl)phosphine Trisodium Salt (TXPTS)

(Matrix presented) Sterically demanding, sulfonated arylphosphines TXPTS and TMAPTS have been applied to the aqueous-phase Heck and Suzuki coupling of aryl bromides. TXPTS provides good yields of Heck coupling products from aryl bromides at 80°C, while both TMAPTS and TPPTS gave significantly less active catalysts. TXPTS is the first ligand to promote the aqueous-phase Heck coupling under such mild conditions. Both TXPTS and TMAPTS provide active catalysts for Suzuki couplings of aryl bromides at 50°C.

Development of a polymer bound Wittig reaction and use in multi-step organic synthesis for the overall conversion of alcohols to β-hydroxyamines

An efficient combinatorial access to β-hydroxyamines suitable for automation is achieved by the mild oxidation of alcohols to aldehydes by polymer supported perruthenate (PSP), the subsequent clean olefination of the obtained aldehydes by polymer supported Wittig reagents followed by the epoxidation of the olefins by dimethyldioxirane (DMDO), and the final aminolysis of the epoxides with various amines is described.

NEW SIMPLE METHOD FOR THE SYNTHESIS OF CIS-STILBENES

A new method involving catalytic acetylenic condensation as the key stage was developed for the synthesis of cis-stilbenes.Subsequent selective hydrogenation of the synthesized alkyltolanes over Pd-CaCO3 gave a series of alkyl-substituted stilbenes. 1,8-Dimethylphenanthrene was obtained from o-iodotoluene.