37166-45-3

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 1066-54-2 trimethylsilylacetylene 
• 201230-82-2 carbon monoxide 
• 624-31-7 4-tolyl iodide 
• 250643-77-7 tris(2-(trimethylsilyl)ethynyl)indium 
• 104-87-0 4-methyl-benzaldehyde 
• 106-38-7 para-bromotoluene 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 

Downstream Products

• 1028865-97-5 rac-1-pyridin-2-yl-2-(4-tolyl)-4-(trimethylsilanyl)but-3-yn-2-ol 
• 1358811-65-0 ethyl 3-(p-tolyl)-5-(trimethylsilyl)thiophene-2-carboxylate 
• 271597-75-2 ethyl 2-methyl-6-(4-tolyl)pyridine-3-carboxylate 
• 14377-18-5 1-(4-methylphenyl)prop-2-yn-1-one 
• 132589-56-1 (Z)-6-<(4'-methylphenyl)methylidene>-1,5-dimethyltricyclo<3.2.1.0^2,7>oct-3-en-8-one 
• 132589-31-2 (E)-6-<(4'-methylphenyl)methylidene>-1,5-dimethyltricyclo<3.2.1.0^2,7>oct-3-en-8-one 
• 132588-81-9 (-)-(S)-2,6-dimethyl-<1'-(4''-methylphenyl)prop-2'-ynyl>aniline 
• 132589-32-3 2,6-dimethyl-4-<1'-(4''-methylphenyl)prop-2'-ynyl>aniline 
• 179249-12-8 (1S)-(+)-1-(4'-methylphenyl)-2-propynol 

Relevant academic research and scientific papers

Preparation method of acetylenic ketone compound

The invention provides a preparation method of an acetylenic ketone compound, which comprises the following step: reacting a compound with a structure as shown in a formula (II) with a compound with a structure as shown in a formula (III) under the action of a catalyst and an alkali to obtain the acetylenic ketone compound with a structure as shown in a formula (I). Compared with the prior art, the method has the advantages that the N-formyl saccharin is used as a carbon monoxide substitute reagent to realize carbonyl insertion reaction of bromo-aromatic hydrocarbon and a terminal alkyne compound under the catalysis of the palladium catalyst, so that the acetylenic ketone compound is obtained, the operation is simple, the raw materials and the reagent are easy to obtain, and the condition is mild; the method avoids the use of inflammable and explosive carbon monoxide gas and formic acid, oxalic acid and other acid corrosive carbon monoxide substitute reagents, the catalytic system is green and environment-friendly, the product is easy to separate and purify, and the high-purity acetylenic ketone compound can be efficiently prepared with a high yield.

An easy access towards quinazolines via an improved protocol for ynones

A simple and convenient method has been developed to accomplish Pt/2,2'-bipyridyl catalyzed acyl Sonagashira coupling for the efficient synthesis of ynones. The reaction display significant tolerance to various functional groups and the methodology has be

Synthesis of Water-Soluble Blue-Emissive Tricyclic 2-Aminopyridinium Salts by Three-Component Coupling-(3+3)-Anellation

The (3+3) anellation of alkynones and cyclic amidines is a novel and unexpected approach to generate intensively blue luminescent tricyclic 2-aminopyridinium salts with quantum yields Φf up to 63 % in water. By implementation into a consecutive three-component reaction, these title compounds are obtained rapidly and efficiently in a diversity-oriented fashion. Most interestingly, these bi- and tricyclic 2-aminopyridinium salts emit in dichloromethane and water solutions, thus making them interesting novel luminophore probes for bioanalytics, as well as in the solid state, thus making them blue emitters with tunable efficiency.

Cascade and Effective Syntheses of Functionalized Tellurophenes

A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.

A phosphine-free, atom-efficient cross-coupling reaction of triorganoindiums with acyl chlorides catalyzed by immobilization of palladium(0) in MCM-41

The first phosphine-free heterogeneous palladium(0)-catalyzed cross-coupling of triorganoindiums with acyl chlorides has been developed that proceeds smoothly in THF at 68 °C and provides a general and powerful tool for the synthesis of various valuable aryl ketones and α,β-acetylenic ketones with high atom-economy and high yield. This phosphine-free heterogeneous palladium(0) catalyst can be easily prepared from commercially available reagents and recovered by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decreases in activity. Our system not only avoids the use of phosphine ligands, but also solves the basic problem of palladium catalyst recovery and reuse.

Consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz syntheses of tri- and tetrasubstituted pyridines

The concatenation of the modified Sonogashira alkynone synthesis and the Bagley-Bohlmann-Rahtz pyridine synthesis gives novel consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz (cBBR) syntheses of tri- and tetrasubstituted pyridines in a one-pot fashion. With these processes 15 differently substituted 3-ethoxycarbonyl 2-methylpyridines can be readily obtained in modest to moderate yields.

Recyclable and reusable PdCl2(PPh3) 2/PEG-2000/H2O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes

PdCl2(PPh3)2 in a mixture of water and poly(ethylene glycol) (PEG-2000) is shown to be an extremely active catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes. The reaction can be conducted under an atmospheric pressure of carbon monoxide at 25 °C with Et3N as a base, yielding a variety of alkynyl ketones in good to excellent yields. Application of this synthetic method to prepare flavones from o-iodophenol and terminal alkynes was also achieved. The isolation of the products is readily achieved by extraction with diethyl ether, and the PdCl2(PPh3)2/PEG-2000/ H2O system can be easily recycled and reused six times without any loss of catalytic activity. the Partner Organisations 2014.

Rapid consecutive three-component coupling-Fiesselmann synthesis of luminescent 2,4-disubstituted thiophenes and oligothiophenes

(Hetero)aroyl chlorides, alkynes, and ethyl 2-mercapto acetate can be reacted in a consecutive three-component synthesis to give 2,4-disubstituted thiophene 5-carboxylates in good to excellent yields. In the sense of a pseudo-five-component reaction highly blue luminescent symmetrical terthiophenes and a quinquethiophene can be synthesized in excellent yield.

Ni(0) catalyzed one step synthesis of benzo[b][1,8] naphthyridin-5-ones from silyl-α-ketoalkynes in water

One-step synthesis of new benzo[b][1,8]naphthyridin-5-ones using a Ni(0) catalytic system in aqueous medium with mild conditions of pressure and temperature is described. It is very interesting to note that Ni(0) catalyst increases the rate of condensation of several α-ketoalkynes with 2-amino-4(1H)-quinolinone obtaining benzo[b][1,8]naphthyridin-5-ones in very high yield. In the absence of catalyst this condensation reaction takes 24 h with a product yield of 10%.

Studies on copper(I) catalysed cross-coupling reactions: A convenient and facile method for the synthesis of diversely substituted α,β-acetylenic ketones

Terminal alkynes reacted with acid chlorides in the presence of cuprous iodide as a catalyst in Et3N at room temperature yielding a number of α, β-acetylenic ketones in good to excellent yields.