23637-42-5

Upstream product

• 100-42-5 styrene 
• 117846-95-4 (E)-2-phenyl-1-propene-1-sulfonyl chloride 
• 52147-97-4 trans 2-phenylethenesulfonyl chloride 
• 98-83-9 isopropenylbenzene 
• 14371-10-9 (E)-3-phenylpropenal 
• 100-52-7 benzaldehyde 
• 585-71-7 (1-bromoethyl)benzne 
• 4747-11-9 α-phenoxyethylbenzene 
• 23275-77-6 1-(1-phenylethyl)-1H-benzo[d][1,2,3]triazole 
• 5769-02-8 2-methyl-2-phenyl[1,3]dithiolane 
• 40391-43-3 (E)-1,4-diphenylpent-1-en-3-ol 

Relevant academic research and scientific papers

Catalytically Generated Allyl Cu(I) Intermediate via Cyclopropene Ring-Opening Coupling en Route to Allylphosphonates

An efficient generation of functionalized allyl copper(I) species via cyclopropene ring-opening coupling reaction is reported, which enables stereoselective access to allylphosphonates. Mechanistic studies uncovered stereochemistry to be controlled by both ligand and substrate electronics, with the latter likely arising from pronounced arene-Cu(I) interaction in electron-deficient substrates. The study unravels a novel approach to access functionalized nucleophilic allylcopper species upon which three-component coupling reactions might be developed.

Method for synthesizing (E,E)-1,4,4-trisubstituted conjugated diene in regioselectivity and stereoselectivity mode

The invention discloses a method for synthesizing (E,E)-1,4,4-trisubstituted conjugated diene in a regioselectivity and stereoselectivity mode. The method comprises the following step: reacting vinyl cyclopropane in an organic solvent at the temperature o

Oxygenation of styrenes catalyzed by N-doped carbon incarcerated cobalt nanoparticles

NCI-Co catalyzed olefin oxygenation reactions were investigated. Among the metals examined, including noble metals, the reaction proceeded specifically on Co catalysts, and nitrogen dopant was crucial for the catalytic activity. The presence of NaBH4 as a hydride source, the corresponding alcohols were obtained in high yields. The substrates bearing a reductant-sensitive functional group were made tolerant by changing the reductant and using an additive, and furthermore, the corresponding ketones were accessed by changing reaction conditions. A preliminary examination of other SOMOphiles suggested that the heterogeneous catalyst systems have the potential to be applied to more general hydrofunctionalization of olefins to form various kinds of bonds. Several mechanistic studies suggested that the reaction proceeded in a heterogeneous manner and formed a radical intermediate on cobalt nanoparticle species.

Photo-induced Decarboxylative Heck-Type Coupling of Unactivated Aliphatic Acids and Terminal Alkenes in the Absence of Sacrificial Hydrogen Acceptors

1,2-Disubstituted alkenes such as vinyl arenes, vinyl silanes, and vinyl boronates are among the most versatile building blocks that can be found in every sector of chemical science. We herein report a noble-metal-free method of accessing such olefins through a photo-induced decarboxylative Heck-type coupling using alkyl carboxylic acids, one of the most ubiquitous building blocks, as the feedstocks. This transformation was achieved in the absence of external oxidants through the synergistic combination of an organo photo-redox catalyst and a cobaloxime catalyst, with H2 and CO2 as the only byproducts. Both control experiments and DFT calculations supported a radical-based mechanism, which eventually led to the development of a selective three-component coupling of aliphatic carboxylic acids, acrylates, and vinyl arenes. More than 90 olefins across a wide range of functionalities were effectively synthesized with this simple protocol.

Iron-promoted elimination of β-thioalkoxy alcohols. Olefination by coupling of a carbonyl group with a dithioacetal

Treatment of propargylic dithiolanes with nBuLi followed by a carbonyl electrophile yields the corresponding propargylic dithioacetals. Upon treatment with 1 equiv of Fe(BCaC)3 and excess MeMgl, elimination of SR and OH moieties from 8 affords the corresponding olefins in satisfactory yield. Benzylic dithioacetals behave similarly. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents.

Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton α to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and α,β-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(β-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a- j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

Synthesis of Substituted 1,3-Dienes by the Reaction of Alkenylsulfonyl Chlorides with Olefins Catalyzed by a Ruthenium(II) Complex

Alkenylsulfonyl chlorides reacted with vinylarenes in the presence of a catalytic amount of dichlorotris(triphenylphosphine)ruthenium(II) to give substituted adducts, which were dehydrochlorinated and desulfonylated successively to form substituted (E,E)-1,3-dienes in good yield.