117954-06-0

Upstream product

• 100-42-5 styrene 
• 123-11-5 4-methoxy-benzaldehyde 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 1694-19-5 p-methoxystilbene 
• 14399-53-2 bis(iodomethyl)zinc 
• 591-51-5 phenyllithium 
• 637-69-4 4-Methoxystyrene 
• 1541-11-3 7-phenylcycloheptatriene 
• 696-62-8 para-iodoanisole 
• 768-60-5 4-methoxyphenylacetylen 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 

Downstream Products

• 20821-97-0 5-(4-methoxyphenyl)-3-phenyl-4,5-dihydroisoxazole 
• 3672-51-3 5-(4-methoxyphenyl)-3-phenylisoxazole 
• 132178-17-7 3-hydroxy-3-(4-methoxyphenyl)-1-phenylpropane-1-one 
• 111008-99-2 3-hydroxy-1-(4-methoxy-phenyl)-3-phenyl-propan-1-one 

Relevant academic research and scientific papers

Electrochemical Ring-Opening Dicarboxylation of Strained Carbon-Carbon Single Bonds with CO2: Facile Synthesis of Diacids and Derivatization into Polyesters

Diacids are important monomers in the polymer industry to construct valuable materials. Dicarboxylation of unsaturated bonds, such as alkenes and alkynes, with CO2 has been demonstrated as a promising synthetic method. However, dicarboxylation of C-C single bonds with CO2 has rarely been investigated. Herein we report a novel electrochemical ring-opening dicarboxylation of C-C single bonds in strained rings with CO2. Structurally diverse glutaric acid and adipic acid derivatives were synthesized from substituted cyclopropanes and cyclobutanes in moderate to high yields. In contrast to oxidative ring openings, this is also the first realization of an electroreductive ring-opening reaction of strained rings, including commercialized ones. Control experiments suggested that radical anions and carbanions might be the key intermediates in this reaction. Moreover, this process features high step and atom economy, mild reaction conditions (1 atm, room temperature), good chemoselectivity and functional group tolerance, low electrolyte concentration, and easy derivatization of the products. Furthermore, we conducted polymerization of the corresponding diesters with diols to obtain a potential UV-shielding material with a self-healing function and a fluorine-containing polyester, whose performance tests showed promising applications.

Modular enantioselective synthesis of cis-cyclopropanes through self-sensitized stereoselective photodecarboxylation with benzothiazolines

Chiral cis-cyclopropanes are strained rigid analogues of alkyl chains, whose study and application are limited by their difficult synthesis. A modular approach from olefin materials is enabled by the discovery of the electron donor-acceptor (EDA) interaction between 2-substituted benzothiazolines and N-hydroxyphthalimide esters. These complexes are activated by visible light without photocatalysts, and the benzothiazoline reagent plays a triple role as a photoreductant, a stereoselective hydrogen-atom donor, and a Br?nsted acid. Beyond the enantioselective synthesis of cis-cyclopropanes, these results introduce benzothiazolines as accessible and easily tunable self-sensitized photoreductants.

Enantioselective Cyclobutenylation of Olefins Using N-Sulfonyl-1,2,3-Triazoles as Vicinal Dicarbene Equivalents

Cyclobutenes are highly useful synthetic intermediates as well as important motifs in bioactive small molecules. Herein, we report a regio-, chemo-, and enantioselective synthesis of cyclobutenes from olefins using N-sulfonyl-1,2,3-triazoles as vicinal dicarbene equivalents or alkyne [2 + 2] cycloaddition surrogates. Terminal and cis-olefins can be transformed into enantioenriched cyclopropanes via rhodium catalysis. Then, in one pot, treatment of these intermediates with tosyl hydrazide and base effects diazo formation followed by rhodium-catalyzed ring expansion to yield enantioenriched cyclobutenes. These cyclobutenes can be transformed into highly substituted, enantioenriched cyclobutanes, including structures relevant to natural product scaffolds.

Synergistic effect of additives on cyclopropanation of olefins

An efficient cyclopropanation of olefins with Zn(CH2I) 2, a catalytic amount of CCl3CO2H, and 1,2-dimethoxyethane at room temperature is described. A wide variety of olefins, including acid-sensitive substrates,

Cyclopropanation with gold(I) carbenes by retro-Buchner reaction from cycloheptatrienes

Cationic gold(I) promotes the retro-Buchner reaction of 7-substituted 1,3,5-cycloheptatrienes, leading to gold(I) carbenes that cyclopropanate alkenes.

The nickel and palladium catalyzed stereoselective cross coupling of cyclopropyl nucleophiles with aryl halides

The reaction of 2-phenylcyclopropylzinc chloride with some substituted (het)aryl halides gave the corresponding coupling products with good yields and stereoselectivities under the influence of a catalytic amount of Pd(PPh3)4. Other Ni- and Pd-catalysts were less efficient. Alkyl-substituted cyclopropyl nucleophiles gave lower yields.

A Practical Cyclopropanation Method using Direct Generation of Organozinc Carbenoids from Carbonyl Compounds

A variety of readily available aryl and α,β-unsaturated carbonyl compounds, on treatment with zinc and 1,2-bis(chlorodimethylsilyl)ethane, afforded organozinc carbenoids which may be trapped with alkenes to give cyclopropanes.