17256-00-7

Upstream product

• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 99-93-4 4-Hydroxyacetophenone 
• 536-74-3 phenylacetylene 
• 108-95-2 phenol 
• 636-41-9 2-methyl-1H-pyrrole 
• 126597-34-0 1-p-hydroxyphenyl-1-phenyl-1-ethanol 
• 100-58-3 phenylmagnesium bromide 
• 98-80-6 phenylboronic acid 
• 3262-89-3 triphenylboroxine 
• 108-86-1 bromobenzene 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 106-41-2 4-bromo-phenol 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 6783-05-7 trans-2-phenylvinylboronic acid 

Downstream Products

• 4333-75-9 1-(4-methoxyphenyl)-1-phenylethene 
• 127943-17-3 trimethyl(4-(1-phenylvinyl)phenoxy)silane 
• 1137-42-4 4-Hydroxybenzophenone 
• 126597-34-0 1-p-hydroxyphenyl-1-phenyl-1-ethanol 

Relevant academic research and scientific papers

Nickel-Catalyzed Direct Synthesis of Aryl Olefins from Ketones and Organoboron Reagents under Neutral Conditions

Nickel-catalyzed addition of arylboron reagents to ketones results in aryl olefins directly. The neutral condition allows acidic protons of alcohols, phenols, and malonates to be present, and fragile structures are also tolerated.

Organocatalytic asymmetric synthesis of 1,1-diarylethanes by transfer hydrogenation

A new organocatalytic transfer hydrogenation strategy for the asymmetric synthesis of 1,1-diarylethanes is described. Under mild conditions, a range of 1,1-diarylethanes substituted with an o-hydroxyphenyl or indole unit could be obtained with excellent efficiency and enantioselectivity. We also extended the protocol to an unprecedented asymmetric hydroarylation of 1,1-diarylalkenes with indoles for the synthesis of a range of highly enantioenriched 1,1,1-triarylethanes bearing acyclic all-carbon quaternary stereocenters. These diaryl- and triarylethanes exhibit impressive cytotoxicity against a number of human cancer cell lines. Preliminary mechanistic studies combined with DFT calculations provided important insight into the reaction mechanism.

Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters

Described herein is a general and mild catalytic asymmetric 1,6-conjugate addition of para-quinone methides (p-QMs), a class of challenging reactions with previous limited success. Benefiting from chiral Bronsted acid catalysis, which allows in situ formation of p-QMs, our reaction expands the scope to general p-QMs with various substitution patterns. It also enables efficient intermolecular formation of all-carbon quaternary stereocenters with high enantioselectivity.

AIBN-catalyzed oxidative cleavage of gem -disubstituted alkenes with O 2 as an oxidant

A 2,2-azobis(isobutyronitrile) (AIBN) catalyzed oxidative cleavage of gem-disubstituted alkenes with molecular oxygen as the oxidant has been described. Carbonyl compounds were obtained as the desired products in high yield under mild conditions. Based on previous documents and current experimental results, a relatively reasonable mechanism is proposed.

Palladium catalyzed coupling of tosylhydrazones with aryl and heteroaryl halides in the absence of external ligands: Synthesis of substituted olefins

Palladium catalyzed cross-coupling reaction of hydrazones with aryl halides in the absence of external ligand is reported. The versatility of this coupling reaction is demonstrated in showcasing the selectivity of coupling reaction in the presence of hydr

Oxime palladacycle-catalyzed Suzuki-Miyaura alkenylation of aryl, heteroaryl, benzyl, and allyl chlorides under microwave irradiation conditions

A simple new protocol for the palladium-catalyzed Suzuki-Miyaura cross-coupling of organic chlorides under microwave irradiation is presented. Deactivated aryl and heteroaryl chlorides are efficiently cross-coupled with alkenylboronic acids and potassium alkenyltrifluoroborates using the 4,4′-dichlorobenzophenone oxime-derived palladacycle 1b as precatalyst in 0.1 to 0.5 mol% palladium loading, tris(tert-butyl)phosphonium tetrafluoroborate {[HP(t-Bu)3]BF4} as ligand, tetra-n-butylammonium hydroxide as cocatalyst, and potassium carbonate as base in N,N- dimethylformamide at 130°C under microwave irradiation conditions. Under these conditions, styrenes, stilbenes, and alkenylarenes are obtained in good to high yields, and with high regio- and diastereoselectivities in only 20 min. The reported protocol is also very efficient for the regioselective alkenylation of benzyl and allyl chlorides to afford allylarenes and 1,4-dienes. Copyright

Synthesis of benzophenones from geminal biaryl ethenes using m-chloroperbenzoic acid

The oxidation of geminal biaryl ethenes 3 and 1,3-enynes 5 using m-chloroperbenzoic acid in dichloromethane at room temperature presents a catalyst-free approach for the synthesis of functionalized benzophenones 4 and ynones 6, respectively.

Nonlinear solvent water effects in the excited-state (formal) intramolecular proton transfer (ESIPT) in m-hydroxy-1,1-diaryl alkenes: Efficient formation of m-quinone methides

The photohydration of hydroxy-substituted 1,1-diaryl alkenes 1-3 has been studied in aqueous CH3CN solution. Evidence for formation of quinone methide intermediates was provided by product studies and by observation of its absorption spectrum by laser flash photolysis. For the meta isomers, the proposed mechanism of m-quinone methide formation probably involves a solvent-mediated ("proton-relay") excited-state (formal) intramolecular proton transfer (ESIPT) from the phenol hydroxyl group to the β-carbon of the alkene moiety in neutral aqueous CH3CN solution, either in a concerted manner or via two very fast steps. The m-quinone methides are then trapped by water to form the corresponding diaryl ethanol product with high overall quantum yield. Evidence for the ESIPT pathway was provided by fluorescence and LFP measurements. The addition of small amounts of water (3CN) decreased the fluorescence emissions of 1 and 2 with a concomitant increase in production of m-quinone methides. Stem-Volmer analyses of fluorescence data revealed a dynamic and a minor static quenching component, both of which involved a water trimer cluster. The degree of charge transfer from the phenol (phenolate) oxygen to the alkene β-carbon, which may be thought of as the driving force for this efficient ESIPT, is pronounced for the meta isomer in the excited state, consistent with Zimmerman's "meta-ortho effect". Alkenes 1 and 2 were shown to be more efficient in m-quinone methide photogeneration than the hydroxy-substituted benzyl alcohol 8, which required conditions of higher water content for similar quantum yields.

Electrophilic Alkenylation of Arometics with Phenylacetylene over Zeolite HSZ-360

Aromatic compounds react with phenylacetylene in the presence of zeolite HSZ-360 affording 1,1-diarylethylenes 3 in good to excellent yields and selectivities.