79135-69-6

Upstream product

• 14720-90-2 1,1-bis-(4-ethyl-phenyl)-2-chloro-ethene 
• 72-56-0 perthane 
• 16331-45-6 p-ethylbenzoyl chloride 
• 25309-64-2 4-ethyl-1-iodobenzene 
• 74-86-2 acetylene 
• 40307-11-7 1-ethyl-4-ethynylbenzene 
• 471-25-0 Propiolic acid 
• 25347-49-3 1,2-bis(p-ethylphenyl)ethylene 
• 79135-70-9 1,2-Dibromo-1,2-bis(p-ethylphenyl)ethane 
• 101783-95-3 1,1-bis-(4-ethyl-phenyl)-2,2-dibromo-ethane 
• 75-20-7 calcium carbide 
• 52436-73-4 4-ethylbenzenediazonium tetrafluoroborate 

Downstream Products

• 25347-49-3 1,2-bis(p-ethylphenyl)ethylene 
• 81734-57-8 4,4'-diethyl-cis-stilbene 
• 1259437-16-5 1,2-bis(4-ethylphenyl)-2-fluoroethanone 
• 1259437-15-4 1,2-bis(4-ethylphenyl)-2-fluoro-1,1-dimethoxyethane 
• 1584633-28-2 1-acetyl-5,6-bis(4-ethylphenyl)pyridin-2(1H)-one 
• 1607447-93-7 C₃₁H₂₇NO₂ 
• 1620140-29-5 (E)-(1,2-bis(4-ethylphenyl)-2-phenylvinyl)(phenyl)sulfane 
• 1620140-44-4 (Z)-(1,2-bis(4-ethylphenyl)-2-phenylvinyl)(phenyl)sulfane 
• 1226974-60-2 2,3-bis(4-ethylphenyl)-1-methyl-1H-indole 

Relevant academic research and scientific papers

Synthesis of Diarylethynes from Aryldiazonium Salts by Using Calcium Carbide as an Alkyne Source in a Deep Eutectic Solvent

An efficient method for the synthesis of diarylethynes from aryldiazonium salts by using calcium carbide as an alkyne source at room temperature in a deep eutectic solvent is described. The salient features of this protocol are an inexpensive and easy-to-handle alkyne source, a nonvolatile and recyclable solvent, mild conditions, and a simple workup procedure.

Selective Synthesis of Non-Aromatic Five-Membered Sulfur Heterocycles from Alkynes by using a Proton Acid/N-Chlorophthalimide System

A multicomponent strategy to achieve two different regioselectivities from alkynes, isothiocyanates and H2O with a proton acid/N-chlorophthalimide (NCPI) system is described to selectively obtain non-aromatic five-membered sulfur heterocycles (1,3-oxathiol-2-imines/thiazol-2(3H)-one derivatives) through multiple bond formations. The process features readily available starting materials, mild reaction conditions, broad substrate scope, good functional-group tolerance, high regio- and chemo- selectivities, gram-scale synthesis and late-stage modifications. Mechanistic studies support the proposal that the transformation process includes a combination of H2O and isothiocyanate, free-radical formation, carbonation and intramolecular cyclization to give the products. Furthermore, the 1,3-oxathiol-2-imine derivatives possess unique fluorescence characteristics and can be used as Pd2+ sensors with a “turn-off” response, demonstrating potential applications in environmental and biological fields.

A novel approach for rhodium(iii)-catalyzed C-H functionalization of 2,2′-bipyridine derivatives with alkynes: A significant substituent effect

We described a novel approach for the C-H functionalization of 2,2′-bipyridine derivatives with alkynes. DFT calculations and experimental data showed a significant substituent effect at the 6-position of 2,2′-bipyridine, which weakened the adjacent N-Rh bond and provided the possibility of subsequent rollover cyclometalation, C-H activation, and functionalization.

Rhodium(iii)-catalyzed unreactive C(sp3)-H alkenylation of N-alkyl-1H-pyrazoles with alkynes

The first example of pyrazole-directed rhodium(iii)-catalyzed unreactive C(sp3)-H alkenylation with alkynes has been described, which showed a relatively broad substrate scope with good functional group compatibility. Moreover, we demonstrated that the transitive coordinating center pyrazole could be easily removed under mild conditions.

Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization

Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.

Palladium-catalyzed oxidative annulation of acrylic acid and amide with alkynes: A practical route to synthesize α-pyrones and pyridones

A range of internal alkynes smoothly underwent palladium-catalyzed oxidative annulations with acrylic acid and amide to afford α-pyrones and pyridones in good to excellent yields with high regioselectivity. The usage of O2 (1 atm) as a stoichiometric oxidant with H2O as the only byproduct under mild conditions makes this process more attractive and practical.

Utility of dysprosium as a reductant in coupling reactions of acyl chlorides: The synthesis of amides and diaryl-substituted acetylenes

Reduction of acyl chlorides with dysprosium metal has been studied. The reducing ability of dysprosium metal is solvent-dependent. Dysprosium metal, which requires neither any additive nor pretreatment, can promote the cross-coupling of acyl chlorides in DMF or DEF to give amides in good yields. When the reaction was performed in N,N-dimethylacetamide, the reductive self-coupling reaction of aroyl chloride took place smoothly and afforded the diaryl-substituted acetylenes in moderate to good yield.

A fine-tuned molybdenum hexacarbonyl/phenol initiator for alkyne metathesis

A new, highly potent activator for molybdenum hexacarbonyl and 2-fluorophenol is described. An "instant" catalyst formed in situ from molybdenum hexacarbonyl and 2-fluorophenol shows high activity for cross- and ring-closing alkyne metathesis reaction. The use of 2-fluorophenol can be combined with other activation methods to allow alkyne metathesis at relatively low temperature (80 °C).

REDUCTIVE COUPLING OF BENZOIC ACID HALIDES AND ESTERS USING LOW-VALENT TITANIUM

The reductive coupling of (substituted) benzoic acid chlorides and esters is achieved using low-valent titanium, generated from TiCl3 and LiAlH4.Both acid chlorides and esters seem to follow the same two reaction pathways: one path via tolanes to stilbenes, the other via benzils to complex mixtures of products arising from reduction and further coupling reactions.Although the exact product balance depends upon the reaction conditions the major product is (substituted) cis-stilbene.

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.