4960-55-8

Upstream product

• 60-29-7 diethyl ether 
• 408351-80-4 3-chloro-1,1,3-triphenyl-propene 
• 124-38-9 carbon dioxide 
• 1674-18-6 tetraphenylallene 
• 68-12-2 N,N-dimethyl-formamide 
• 96165-46-7 Lithium 2-lithio-1,1,3,3-tetraphenylpropenide 
• 530-48-3 1,1-Diphenylethylene 
• 908093-98-1 diazodiphenylmethane 
• 90-99-3 diphenylchloromethane 
• 41326-74-3 2,2,4,4-Tetraphenyl-3-butenaldehyde 
• 21711-85-3 1,1,3-triphenyl-4-hydroxyprop-1-ene 
• 94-41-7 benzalacetophenone 
• 1165952-92-0 cyclohexa-1,4-diene 
• 4214-38-4 (diphenylmethylene)triphenylphosphorane 

Downstream Products

• 119-61-9 benzophenone 
• 117-34-0 2,2-diphenylacetic acid 
• 1450-63-1 1,1,4,4-tetraphenyl-1,3-butadiene 
• 36171-50-3 1,1,3,3-tetraphenylpropane 
• 31366-67-3 1,2,3-triphenylindan 
• 104217-70-1 1,1,3,3-tetraphenylbutane 
• 94234-95-4 2-(diphenylmethyl)-1,1,3,3-tetraphenylpropene 
• 2510-22-7 4-pyridylacetylene 
• 74589-99-4 potassium salt of 1,1,3,3-tetraphenylpropene 
• 37972-24-0 2-ethynylpyrimidine 
• 947-91-1 Diphenylacetaldehyde 
• 1674-18-6 tetraphenylallene 
• 116030-16-1 1,1,2,3-tetraphenylpropane 
• 6925-58-2 3-<2H>-1,1,3,3-tetraphenylpropene 

Relevant academic research and scientific papers

Synthesis of internal olefins by direct coupling of alcohols and olefins over MoΒ zeolite

An efficient and novel Moβ zeolite catalyzed sp2-sp3 C–C bond development reaction over the direct coupling of alcohols and alkenes has been performed in solvent free environment. The current method gives an attractive access to a wide variety of polysubstituted alkenes in good to excellent yields. The Moβ zeolite was effectively reused for up to 5 successive cycles.

Experimental Evidence for p Ka-Driven Asynchronicity in C-H Activation by a Terminal Co(III)-Oxo Complex

C-H activation by transition metal oxo complexes is a fundamental reaction in oxidative chemistry carried out by both biological and synthetic systems. This centrality has motivated efforts to understand the patterns and mechanisms of such reactivity. We have therefore thoroughly examined the C-H activation reactivity of the recently synthesized and characterized late transition metal oxo complex PhB (tBuIm)3CoIIIO. Precise values for the pKa and BDFEO-H of the conjugates of this complex have been experimentally determined and provide insight into the observed reactivity. The activation parameters for the reaction between this complex and 9,10-dihydroanthracene have also been measured and compared to previous literature examples. Evaluation of the rates of reaction of PhB(tBuIm)3CoIIIO with a variety of hydrogen atom donors demonstrates that the reactivity of this complex is dependent on the pKa of the substrate of interest rather than the BDEC-H. This observation runs counter to the commonly cited reactivity paradigm for many other transition metal oxo complexes. Experimental and computational analysis of C-H activation reactions by PhB(tBuIm)3CoIIIO reveals that the transition state for these processes contains significant proton transfer character. Nevertheless, additional experiments strongly suggest that the reaction does not occur via a stepwise process, leading to the conclusion that C-H activation by this CoIII-oxo complex proceeds by a pKa-driven "asynchronous" concerted mechanism. This result supports a new pattern of reactivity that may be applicable to other systems and could result in alternative selectivity for C-H activation reactions mediated by transition metal oxo complexes.

Nickel-Catalyzed Benzylation of Aryl Alkenes with Benzylamines via C-N Bond Activation

We have developed the first example of nickel-catalyzed Heck-type benzylation of aryl olefins with various benzylamines as benzyl electrophiles, and the benzylic C-N bond cleavage was efficiently promoted by the amine-I2 charge transfer complex (CT complex). The combination of low-cost NiCl2 and I2 has been found to facilitate Heck reaction of tertiary benzylamines and alkenes into various benzyl-substituted alkenes in good to excellent yields. This unconventional Heck reaction is proposed to go through initially the formation of a benzylic radical via oxidative addition of the C-N bond with Ni(0), then capturing by aryl alkene via radical addition, followed by single-electron transfer redox and proton abstraction without oxidant and external base.

Lewis base-assisted Lewis acid-catalyzed selective alkene formation via alcohol dehydration and synthesis of 2-cinnamyl-1,3-dicarbonyl compounds from 2-aryl-3,4-dihydropyrans

Acid-catalyzed dehydration of alcohols has been widely employed for the synthesis of alkenes. However, activated alcohols when employed as substrates in dehydration reactions are often plagued by the lack of alkene selectivity. In this work, the reaction system can be significantly improved through enhancing the performance of Lewis acid catalysts in the dehydration of activated alcohols by combining with a Lewis base. Observations of the reaction mechanism revealed that the Lewis base component might have changed the reaction rate order. Although both the principal and side reaction rates decreased, the effect was markedly more observed on the latter reaction. Therefore, the selectivity of the dehydration reaction was improved. On the basis of this observation, a new route to synthesize 2-cinnamyl-1,3-dicarbonyl compounds was developed by using 2-aryl-3,4-dihydropyran as a starting substrate in the presence of a Lewis acid/Lewis base combined catalyst system.

Silica-supported policresulen as a solid acid catalyst for organic reactions

A new type of solid catalyst was prepared by coating a thin layer of policresulen, an inexpensive polymer prepared via condensation of 2-hydroxy-4-methylbenzenesulfonic acid and formaldehyde that has been used as commercially available drug, onto the surface of silica. The policresulen component is insoluble in many organic solvents and can be adsorbed on silica with the aid of hydrogen bonding. The obtained silica/policresulen composite showed remarkable catalytic activity for various organic reactions. In model reactions, the catalyst can be recycled several times without significant loss of activity. The salient features of using this acid catalyst in organic reactions include cost-effectiveness, simple and time-efficient preparation, and the convenience of controlling the acid loading on the solid.

Metal-free and recyclable route to synthesize polysubstituted olefins via C-C bond construction from direct dehydrative coupling of alcohols or alkenes with alcohols catalyzed by sulfonic acid-functionalized ionic liquids

A direct synthesis of polysubstituted olefins via construction of C-C bonds, which involves the direct dehydrative coupling of alcohols or alkenes with alcohols, was realized using a series of alkanesulfonic acid group-functionalized ionic liquids (SO3H-functionlization ILs) without additives. The metal-free and recyclable catalyst system avoided the disposal and neutralization of acidic catalysts after reaction and tolerated a broad range of substrates, including benzylic, allyl, propargylic, aliphatic and aromatic or aliphatic olefins. Additionally, the catalytic system was suitable for a gram-scale preparation. Preliminary mechanistic studies indicated that the C-H bond cleavage in this reaction might be involved in the rate-determining step.

Direct electrosynthesis of ketones from benzylic methylenes by electrooxidative C-H activation

Electrify your chemistry! Direct electrosynthesis of ketones from benzylic methylenes in an undivided cell was realized in moderate to good yields (see scheme). In this electrosynthesis, electrons instead of conventional oxidants and catalysts are employed to make the reaction environmentally benign. Moreover, the reaction intermediate radical was detected by ESR spectroscopy and the reaction mechanism was clarified.

Metal-free hydrogenation of electron-poor allenes and alkenes

The poorer, the better: A metal-free catalytic procedure for the reduction of electron-poor allenes and alkenes has been developed. The method employs a frustrated Lewis pair based catalyst. 1,4-Diazabicyclo[2.2.2]octane (DABCO)/B(C6F5)3 was shown to be the best combination in optimization studies. Copyright

Sp3-sp2 C-C bond formation via Bronsted acid trifluoromethanesulfonic acid-catalyzed direct coupling reaction of alcohols and alkenes

A novel and efficient trifluoromethanesulfonic acid-catalyzed sp 3-sp2 Ci￡C bond formation reaction through the direct coupling of alcohols with alkenes has been realized under mild conditions. The present protocol provides an attractive approach to a diverse range of polysubstituted olefins in good to excellent yields with high stereo- and regioselectivities. Copyright

Iron-catalyzed stereospecific olefin synthesis by direct coupling of alcohols and alkenes with alcohols

Chemical equations presented. An efficient Fe(III)-catalyzed direct coupling of alkenes with alcohols and cross-coupling of alcohols with alcohols to give the corresponding substituted (E)-alkenes stereospecifically is demonstrated. Additionally, this reaction could be scaled up. The kinetic isotope effect (KIE) experiments indicated a typical secondary isotope effect in this process. Although benzylic alcohols were effective substrates, mild conditions, atom efficiency, environmental soundness, and stereospecificity are features that make this procedure very attractive.