70855-14-0

Upstream product

• 70855-13-9 1-(4-methylphenyl)-hexane-2,5-dione 
• 31614-66-1 tributyl(p-tolyl)stannane 
• 128455-37-8 2-iodo-3-methyl-2-cyclopenten-1-one 
• 72538-33-1 2-p-tolylnitroethane 
• 78-94-4 methyl vinyl ketone 
• 201230-82-2 carbon monoxide 
• 2749-93-1 1-methyl-4-(1-propyn-1-yl)benzene 
• 321155-39-9 dimethyl(2-pyridinyl)(vinyl)silane 
• 7559-36-6 4-methyl-β-nitrostyrene 
• 70855-12-8 2-Methyl-5-<(4-methylphenyl)methyl>furan 
• 2758-18-1 3-Methyl-2-cyclopenten-1-one 
• 106-38-7 para-bromotoluene 
• 104-81-4 4-Methylbenzyl bromide 
• 105938-95-2 (Z)-4-Chloro-5-p-tolyl-pent-3-enoic acid 

Downstream Products

• 55873-31-9 3,3-dimethyl-2-p-tolylcyclopentenone 

Relevant academic research and scientific papers

Ligand Control of Palladium-Catalyzed Site-Selective α- and γ-Arylation of α,β-Unsaturated Ketones with (Hetero)aryl Halides

This study describes the first palladium-catalyzed, site-selective α- and γ-arylation of α,β-unsaturated ketones with (hetero)aryl halides. A wide range of hetero(aryl)halides coupled with α,β-unsaturated ketones, and transformation into the arylated products proceeded with excellent to good yields. The site selectivity of the reaction is switchable by simply changing the phosphine ligand to access either α-arylated or γ-arylated products in good to excellent yields by using a low catalyst loading, and the method demonstrates good functional-group compatibility.

Catalytic intermolecular Pauson-Khand-type reaction: Strong directing effect of pyridylsilyl and pyrimidylsilyl groups and isolation of Ru complexes relevant to catalytic reaction

Some circumstantial evidence for the directing effect of the 2-pyhdylsilyl group in the Ru-catalyzed intermolecular Pauson-Khand-type reaction (PKR) of alkenyl(2-pyridyl)silane, alkyne, and carbon monoxide has been provided. Most importantly, we have succeeded in isolating several monometallic Ru complexes relevant to the catalytic reaction: Ru(vinylsilane)(CO)3 complexes and ruthenacyclopentene. While the stoichimetric reaction of the Ru(vinylsilane)(CO)3 complex with an alkyne led to the formation of the corresponding cyclopentenone (PKR product) at 100 °C, the ruthenacyclopentene intermediate was quantitatively produced at 50 °C. This complex was also converted to a cyclopentenone upon heating at 100 °C. Moreover, it was also found that the Ru(vinylsilane)(CO)3 complex and ruthenacyclopentene serve as catalysts in intermolecular PKR.

One-pot synthesis of γ-diketones, γ-keto esters, and conjugated cyclopentenones from nitroalkanes

Conjugated addition of primary nitroalkanes to α,β-unsaturated ketones or α,β-unsaturated esters, in the presence of two equivalents of DBU, allows the one-pot prepration of γ-diketones or γ-keto esters, respectively. When 2-aryl-1-nitroethane derivatives

Modified stille coupling utilizing α-iodoenones

α-Iodoenones undergo Pd-catalyzed coupling with alkenyl- and aryltributylstannanes providing an efficient route to the corresponding α-substituted enones.

AN IMPROVED, SIMPLE SYNTHESIS OF 3-METHYL-2-(4-METHYLPHENYL) CYCLOPENTEN-2-ONE: AN IMPORTANT INTERMEDIATE IN CUPARENE SYNTHESIS

Conjugate addition of phenyl-1-methyl-4-(2-nitroethyl) to methyl vinyl ketone in presence of basic alumina, following by Nef reaction and basic cyclization, affords 3-methyl-2-(4-methyl phenyl) cyclopenten-2-one in good yield.

A CONVENIENT METHOD FOR THE SYNTHESIS OF 4-CHLORO-3-ALKENOIC ACID, A NEW USEFUL SYNTHETIC BLOCK FOR 4-OXOALKANOIC AND 4-OXO-2-ALKENOIC ACIDS

Easily available material, β-(1-chlorovinyl)-β-propiolactone reacted with organocopper reagents to afford 4-chloro-3-alkenoic acids in high yields.The acids were easily transformed into two kinds of useful carboxylic acids such as 4-oxoalkanoic and 4-oxo-(E)-2-alkenoic acids leading to various natural products.

Ring Expansion of Succinoin Derivatives. New Synthetic Routes to Cyclopentenones

Acid-catalysed ring expansion reactions of cyclobutane derivatives bearing a vicinal substituted-diol group give α-aryl and α-vinyl substituted cyclopentenones in good yields.

A Simple and Efficient Total Synthesis of the Sesquiterpenes Cuparene and Iso-α-curcumene, from Furan Derivatives

3,3-Dimethyl-2-p-tolylcyclopentanone (7) was synthesised by 1,4-addition of lithium dimethylcuprate to 3-methyl-2-p-tolylcyclopentenone (6), which was derived from 5-methyl-2-(4-methylbenzyl)furan (4) through the diketone (5).Starting from the same intermediate (5), 2-p-tolylheptan-6-one (16) was also synthesised.These results constitute formal total syntheses of cuparene (9) and iso-α-curcumene (17) respectively.