72033-82-0

Upstream product

• 105654-27-1 (Z,Z)-bis(2-phenylethenyl)telluride 
• 121758-59-6 (Z,Z)-bis(p-metylstyryl) telluride 
• 4412-45-7 trans-p-methyl-β-chlorostyrene 
• 2386-64-3 ethylmagnesium chloride 
• 60655-80-3 (E)-4-methylstyrenyl bromide 
• 156423-16-4 (E)-1-(2-iodovinyl)-4-methylbenzene 
• 104-82-5 4-Methylbenzyl chloride 
• 1504-75-2 3-(4-methylphenyl)acrylaldehyde 
• 56578-35-9 4-methyl-cinnamaldehyde 
• 2378-86-1 4-methylbenzyltriphenylphosphonium bromide 
• 72316-17-7 (E)-2-(4-methylphenyl)ethenylboronic acid 
• 110-15-6 succinic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 54948-52-6 1,2,5-tri-p-tolyl-1H-phosphole 
• 222158-85-2 (3aS,7aR)-4,7-Di-p-tolyl-3a,7a-dihydro-isobenzofuran-1,3-dione 
• 66365-87-5 1,2,5-tri-p-tolyl-1H-phosphole 1-oxide 
• 1287736-93-9 2-phenyl-3,5-di-p-tolylpyridine 

Relevant academic research and scientific papers

Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C-H Bonds

A novel, atom economical, and transition-metal-free strategy for the synthesis of thiophenes from substituted buta-1-enes with potassium sulfide has been presented. The reaction achieves double C-S bond formations via cleavage of multiple C-H bonds and provides an efficient approach to access various functionalized thiophenes. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4-diaryl-1,3-dienes. Mechanistically, DMSO plays a role of oxidant and S3?- in situ generated from K2S is involved.

PHOSPHACYCLE COMPOUND AND PROCESS FOR PRODUCTION THEREOF

The invention relates to oligomerization of olefins, such as ethylene, to higher olefins, such as a mixture of 1-hexene and 1-octene, using a catalyst system that comprises a) a source of chromium b) one or more activators and c) a phosphacycle-containing ligating compound. Additionally, the invention relates to a phosphacycle-containing ligating compound and a process for making said compound.

Pd-catalyzed oxidative homo-coupling of acrylates and aromatic alkenes for the conjugated diene synthesis

We developed a bidentate monoanionic nitrogen ligand that was effective in the Pd-catalyzed oxidative homo-coupling reaction of acrylates and aromatic alkenes. In the presence of Pd(OAc)2/ligand several conjugated dienes were obtained in good yields with high stereoselectivities.

Synthesis of Unsymmetric Monosubstituted and Disubstituted Dinaphthothiophenes

Dinaphthothiophenes (DNTs) are a class of compounds with potential uses in organic semiconductors and the synthesis of unsymmetric catalysts. Symmetrical or asymmetrical addition of functional groups to the DNT structure may be desired for steric bulk in binaphthyl catalyst synthesis or tuning the electronic properties of semiconductors. Thus, versatility of functional group addition is a great asset in DNT synthesis. Until now, no versatile and concise methods for the synthesis of unsymmetrically substituted DNTs have been reported. Herein, we report three synthetic routes for the creation of three different classes of DNTs. Each route involves the successive addition of two functionalized styryl groups to a thiophene ring, followed by a photocyclization to form the desired asymmetric DNT. Various novel unsymmetrically monosubstituted and disubstituted dinaphtho[2,1-b:1′,2′-d]thiophenes, dinaphtho[1,2-b:1′,2′-d]thiophenes, and dinaphtho[1,2-b:2′,1′-d]thiophenes were synthesized from 2-bromothiophene,2,4-dibromothiophene, and 3,4-dibromothiophene in three or four steps. These methods can be used to synthesize a wide variety of unsymmetrically functionalized DNTs.

Copper(I)-catalyzed stereoselective hydrogenation of 1,3-diynes and enynes

A stereoselective hydrogenation of 1,3-diynes with an air-stable copper(I)/N-heterocyclic carbene complex, [IPrCuOH], has been developed. The corresponding products, 1,3-dienes, are obtained in a stereoselective manner depending on their substitution pattern: Diaryl-diynes yield E,E-1,3-dienes, whereas dialkyl-diynes are converted to the corresponding Z,Z-1,3-dienes. Hydrogenation and deuteration experiments with enynes indicate that these are competent reaction intermediates in the hydrogenation of diynes.

Catalytic Dehydrogenative C-C Coupling by a Pincer-Ligated Iridium Complex

The pincer-iridium fragment (iPrPCP)Ir (RPCP = ?3-2,6-C6H3(CH2PR2)2) has been found to catalyze the dehydrogenative coupling of vinyl arenes to afford predominantly (E,E)-1,4-diaryl-1,3-butadienes. The eliminated hydrogen can undergo addition to another molecule of vinyl arene, resulting in an overall disproportionation reaction with 1 equiv of ethyl arene formed for each equivalent of diarylbutadiene produced. Alternatively, sacrificial hydrogen acceptors (e.g., tert-butylethylene) can be added to the solution for this purpose. Diarylbutadienes are isolated in moderate to good yields, up to ca. 90% based on the disproportionation reaction. The results of DFT calculations and experiments with substituted styrenes indicate that the coupling proceeds via double C-H addition of a styrene molecule, at β-vinyl and ortho-aryl positions, to give an iridium(III) metalloindene intermediate; this intermediate then adds a β-vinyl C-H bond of a second styrene molecule before reductively eliminating product. Several metalloindene complexes have been isolated and crystallographically characterized. In accord with the proposed mechanism, substitution at the ortho-aryl positions of the styrene precludes dehydrogenative homocoupling. In the case of 2,4,6-trimethylstyrene, dehydrogenative coupling of β-vinyl and ortho-methyl C-H bonds affords dimethylindene, demonstrating that the dehydrogenative coupling is not limited to C(sp2)-H bonds.

Effect of substituents and conjugated chain length on the UV spectra of α,ω-di-substituted phenyl polyenes

A series of α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3) were synthesized, and their ultraviolet (UV) absorption maximum wavelength were determined. The correlation between molecular structure and the maximum wavelength energy (wavenumber/cm -1) was carried out. The results show that the maximum wavelength energy of the title compounds is mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. In the case of the compounds containing NO2 or NH2 groups, the influence of interaction of polarity parameters on the maximum wavelength energy must also be considered. In addition, the exploration was also made for the quantifying correlation of UV absorption maximum wavelength energy with the conjugated polarizability potential CPP replacing the parent molecular absorption energy. And the results indicate that the equation with CPP parameters is more accurate and convenient. Copyright 2013 John Wiley & Sons, Ltd. For the α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3), their ultraviolet absorption maximum wavelength energy (wavenumber/cm-1) was mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. Copyright

Oxidative cross-coupling of vinylsilanes in water

Palladium-promoted cross-dimerization reaction of alkenylsilanes is reported for the first time, which is also one of the very first studies on oxidative cross-coupling between vinylic organometallic reagents. The reaction occurs at room temperature in aqueous micelles and represents a convenient access to all-trans push-pull butadienes.

Reactivity differences between 2,4- and 2,5-disubstituted zirconacyclopentadienes: A highly selective and general approach to 2,4-disubstituted phospholes

Mixtures of 2,4- and 2,5-disubstituted zirconacyclopentadienes were obtained by the reductive dimerisation of terminal alkynes using the Cp 2ZrCl2/lanthanum system. Reactions of dihalophosphines with these mixtures afforded selectively the corresponding 2,4-disubstituted phospholes and 1,4-disubstituted butadienes. A new series of phospholes was characterized by multi-nuclear NMR spectroscopy and X-ray analysis. A possible explanation for the observed selectivity was obtained from X-ray studies and DFT analysis of the intermediate zirconacyclopentadienes. The Royal Society of Chemistry 2013.

Iron-catalysed, hydride-mediated reductive cross-coupling of vinyl halides and Grignard reagents

An iron-catalysed, hydride-mediated reductive cross-coupling reaction has been developed for the preparation of alkanes. Using a bench-stable iron(ii) pre-catalyst, reductive cross-coupling of vinyl iodides, bromides and chlorides with aryl- and alkyl Grignard reagents successfully gave the products of formal sp3-sp3 cross-coupling reactions.