61187-40-4

Upstream product

• 201230-82-2 carbon monoxide 
• 77412-96-5 1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene 
• 126781-85-9 1-(tert-butyl)-4-(methoxymethylene)cyclohexane 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 111036-60-3 2-Benzenesulfinyl-6-tert-butyl-1-oxa-spiro[2.5]octane 
• 83911-67-5 2-Benzenesulfonyl-6-tert-butyl-1-oxa-spiro[2.5]octane 
• 135942-77-7 {5-tert-Butyl-2-[1-methoxy-meth-(Z)-ylidene]-cyclohexylsulfanyl}-benzene 
• 96133-27-6 4-tert-butyl-1-iodo-1-cyclohexene 
• 6353-54-4 4-tert-butyl-1-methylcyclohexanol 
• 60774-46-1 4-tert-butyl-2-phenylsulfanylcyclohexanone 

Downstream Products

• 22173-19-9 4-tert-butyl-1-cyclohexene-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System

A highly efficient and practical Pd(II)/Cu(OAc)2-catalyst system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical approach to preparing enals and also suggests new insight into the Pd(II)/Cu(II)-catalyst system for dehydrogenation of carbonyl compounds and decreasing Pd-catalyst loadings.

Method for preparing olefine aldehyde through catalytic oxidation of enol ether

The invention relates to the technical field of olefine aldehyde preparation, and provides a method for preparing olefine aldehyde through catalytic oxidation of enol ether. According to the invention, a palladium catalyst, a copper salt, a solvent and enol ether are mixed and subjected to a catalytic oxidation reaction to obtain olefine aldehyde. According to the method, the copper salt is used as the oxidizing agent, the mixed solvent of water and acetonitrile is used as the reaction solvent, and the volume ratio of water to acetonitrile in the mixed solvent is controlled to be (3-7): (3-7), so that the catalytic oxidation reaction can be smoothly carried out in the mixed solvent with a specific ratio, and the generation of palladium black precipitate can be avoided. The method provided by the invention has the advantages of simple steps, low reagent cost, no need of dangerous reagents, wide substrate adaptability and small catalyst dosage. Furthermore, octadecane mercaptan is added to promote the catalytic oxidation reaction, and when the dosage of the palladium catalyst is extremely low, the olefine aldehyde yield can be greatly increased by adding octadecane mercaptan.

Pd-Catalyzed Carbonylation of Vinyl Triflates to Afford α,β-Unsaturated Aldehydes, Esters, and Amides under Mild Conditions

An efficient and general protocol for the synthesis of α,β-unsaturated aldehydes, esters, and amides via carbonylation of vinyl triflates including derivatives of camphor, ketoisophorone, verbenone, and pulegone was developed. Crucial for these transformations is the use of a specific palladium catalyst containing a pyridyl-substituted dtbpx-type ligand. This procedure also allows for an easy access of dicarbonylated products from the corresponding ketones.

Palladium-catalyzed reactions of enol ethers: Access to enals, furans, and dihydrofurans

The palladium-catalyzed oxidation of alkyl enol ethers to enals, which employs low loadings of a palladium catalyst, is described. The mild oxidation conditions tolerate a diverse array of functional groups, while allowing the formation of di-, tri-, and tetrasubtituted olefins. The application of this methodology to intramolecular reactions of alkyl enol ethers containing pendant alcohols provides furan and 2,5-dihydrofuran products.

Palladium catalysts for the formylation of vinyl triflates to form α,β-unsaturated aldehydes

(Chemical Equation Presented) What a gas! Synthesis gas is the formylating agent in the efficient one-step title transformation promoted by a palladium catalyst with the bidentate ligand 1,2-bis(di-1-adamantylphosphinomethyl)benzene (see scheme). This method enables the conversion of six-to eight-membered-ring triflates into α,β-unsaturated aldehydes and the introduction of a formyl group into derivatives of elaborate natural compounds. Tf = trifluoromethanesulfonyl.

An efficient procedure for palladium-catalyzed hydroformylation of aryl/enol triflates

An efficient method for hydroformylation of aryl and enol trifluoromethanesulfonates is presented. Their reaction with carbon monoxide, trioctylsilane, and triethylamine in the presence of a catalytic amount of palladium acetate and 1,3-bis(diphenylphosphanyl)propane proceeds efficiently to provide a variety of aromatic and α,β-unsaturated aldehydes.

INDUCTION PAR LA LUMIERE DE L'OXYDATION DES COMPLEXES Η3-ALLYLPALLADIUM PAR L'OXYGENE MOLECULAIRE

Irradiation at λ=366 nm of oxygenated solutions of η3-allylpalladium complexes leads to unsaturated carbonyl compounds.Substitution of the η3-allyl ligand by an electron withdrawing group could induce a regioselective oxidation of the allylic position farthest from this group.The efficiency of these reactions is sensible to the nature of the solvent.

α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. X. An Improved Synthesis of α,β-Unsaturated Carbonyl Compounds from Carbonyl Compounds with Carbon Homologation through α,β-Epoxy Sulfoxides

Treatment of the α,β-epoxy sulfoxides derived from ketones and chloromethyl phenyl sulfoxide or 1-chloroalkyl phenyl sulfoxides with lithium perchlorate in the presence of tributylphosphine oxide in toluene at 110 deg C for about 1-3 h gave α,β-unsaturated aldehydes or α,β-unsaturated ketones in high yields.In contrast to these results, the α,β-epoxy sulfoxides derived from aldehydes did not give the desired α,β-unsaturated ketones.In this case, a sequential treatment of the α,β-epoxy sulfoxides with benzenethiolate and m-chloroperbenzoic acid afforded α-phenylsulfinylated ketones, which were heated in toluene at 110 deg C to give the desired enones in good overall yields.The oxidation of the α,β-unsaturated aldehydes obtained by this method gave α,β-unsaturated carboxylic acids in high yields.These procedures afforded a new method for the synthesis of α,β-unsaturated carbonyl compounds, including α,β-unsaturated esters, from carbonyl compounds with carbon homologation.

Preparation stereoselective de methyle cetones α-bromees: stereochimie de l'addition d'anions en α d'un groupe sulfone sur des cyclohexanones monocycliques et steroidiques

This work describes stereochemical results obtained for the preparation of α-bromomethyl ketones or α-bromoaldehydes starting from monocyclic and steroid cyclohexanones, using the Durst method.In all the cases studied here, the bromine is introduced selectively in the equatorial position.However, for monocyclic compounds, the yields of α-bromocarbonyl compounds are limited by the competitive formation of α-ethylenic carbonyl compounds.