39728-15-9

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 75085-60-8 1,5-diphenyl-3-trimethylsilyl-1-pentyn-3-ol 
• 129866-69-9 (E)-3-phenyl-2-propeneselenoic acid Se-phenyl ester 
• 67-56-1 methanol 
• 35225-79-7 dibenzylideneacetone 
• 145822-73-7 (E)-2-Benzyl-3-oxo-5-phenyl-pent-4-enoic acid tert-butyl ester 
• 536-74-3 phenylacetylene 
• 31984-10-8 1-bromo-4-phenylbutan-2-one 
• 538-58-9 1,5-diphenyl-1,4-pentadiene-3-one 
• 39728-06-8 C₂₀H₂₆NO⁽¹⁺⁾*CH₃O₄S^(1-) 
• 77681-22-2 (Z)-N-benzylidenebenzylamine N-oxide 

Downstream Products

• 859179-38-7 3-benzyl-2,4-dioxo-6-phenyl-cyclohexanecarboxylic acid ethyl ester 
• 109690-78-0 2-benzyl-5-phenyl-cyclohexane-1,3-dione 
• 112082-92-5 (+/-)-5-phenyl-7-oxo-5,6,7,8-tetrahydro-9H-benzocycloheptene 
• 940286-90-8 (1E)-1,5-diphenylpent-1-en-3-ol 
• 1454308-54-3 1,5-diphenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pentan-3-on 

Relevant academic research and scientific papers

Cationic Palladium(II)-Diphosphine Complexes as Catalysts for the Carbonylation of Alkenes to Ketones

Cation palladium complexes of the type 2 2 are active catalysts for the carbonylation to ketones, e.g., for the selective formation of E-1,5-diphenylpen

Photocatalytic Stoichiometric Oxidant-Free Synthesis of Linear Unsaturated Ketones from 1,2-Disubstituted Cyclopropanols

A one-step catalytic oxidant-free synthesis of unsaturated ketones from 1,2-disubstituted cyclopropanols is reported. Previously for this transformation, only two- and three-step protocols have been developed. The reaction proceeds under irradiation with visible light in the presence of catalytic amounts of both an acridinium photocatalyst and a cobaloxime complex. 2-Aryl-substituted cyclopropanols react giving α,β-unsaturated ketones, while dehydrogenative ring opening of 2-alkyl-substituted substrates affords mixtures of α,β- and β,γ-enones. The reaction starts with one-electron oxidation of a cyclopropanol to cyclopropyloxy radical, presumably, by the photoexcited acridinium catalyst. We also found that Co(dmgBF 2) 2(MeCN) 2complex under an air atmosphere and irradiation with blue LEDs or upon heating can serve as a hydroxycyclopropane oxidant.

Recyclable Polyisobutylene-Bound HMPA as an Organocatalyst in Recyclable Poly(α-olefin) Solvents

This work describes the synthesis of a PIB-bound hexamethylphosphoramide (HMPA) analog and its applications as a recyclable catalyst in allylation of aldehydes and reduction of enones in a recyclable poly(α-olefin) (PAO) polymeric solvent. Kinetic studies of the allylation reaction show that this PIB-bound HMPA analog is as active as HMPA in dichloromethane and PAO and that this PIB-bound catalyst is comparably reactive in heptane and in a PAO solvent. The PIB-bound HMPA catalyst has high phase selective solubility in PAO versus a polar solvent. By using this catalyst in a nonvolatile separable PAO solvent, this catalyst recyclability can be coupled to solvent recyclability, something that is less feasible in a conventional heptane solvent. The result is good recycling of catalyst and solvent through at least 5 cycles using simple gravity-based liquid/liquid extractions. This is in contrast to HMPA or conventional solvents which are less recyclable.

Hydrogenation of Ketones and Esters Catalyzed by Pd/C?SiO2

Hydrogenation of unsaturated ketones and esters with molecular hydrogen on the 5%Pd/C?SiO2 heterogeneous catalyst has been studied. The reaction direction and yield are determined by the starting compounds structure. Hydrogenation of unsaturated ketones containing phenyl group at the double carbon–carbon atom is accompanied by the reduction of the ketone group into the alcohol one. Hydrogenation of unsaturated esters is accompanied by transesterification.

Zinc mediated direct transformation of propargyl N-hydroxylamines to α,β-unsaturated ketones and mechanistic insight

A Lewis acid catalyzed direct transformation of propargyl N-hydroxylamines to α,β-unsaturated ketones in the presence of aqueous Zn(II)-salts has been described. This investigation also provides a novel observation for the stoichiometric role of Zn-halides over what is known to date for catalytic processes. A thorough mechanistic study has been established based on the experiment using18O-labeled water in optimized reaction conditions; the incorporation of18O in the desired product was also substantiated by HRMS. This methodology is also a mild, inexpensive, and an efficient approach for this unusual conversion.

Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines

A new strategy has been established for the kinetic resolution of racemic allylic alcohols through a palladium/sulfonyl-hydrazide-catalyzed asymmetric OH-substitution under mild conditions. In the presence of 1 mol % [Pd(allyl)Cl]2, 4 mol % (S)-SegPhos, and 10 mol % 2,5-dichlorobenzenesulfonyl hydrazide, a range of racemic allylic alcohols were smoothly resolved with selectivity factors of more than 400 through an asymmetric allylic alkylation of monosubstituted hydrazines under air at room temperature. Importantly, this kinetic resolution process provided various allylic alcohols and allylic hydrazine derivatives with high enantiopurity.

Ruthenium-catalyzed conjugate hydrogenation of ?±,?2-enones by in situ generated dihydrogen from paraformaldehyde and water

Notwithstanding that the highly selective hydrogenation of ?±,?2-enones to allylic alcohols can be realized by using Noyori's Ru bifunctional system, the selective reduction of the C=C bonds in ?±,?2-enones without touching the C=O bonds still lacks a general, simple, and efficient procedure. Ruthenium-catalyzed conjugate hydrogenation of various ?±,?2-enones to saturated ketones with high selectivity was investigated. The most important feature of this procedure was that hydrogen in situ generated from paraformaldehyde (or formalin) and water was employed as the reductant.

Palladium-catalyzed carbonylative dimerization of styrenes to 1,5-diarylpent-1-en-3-ones

A general palladium-catalyzed carbonylative dimerization of styrenes has been developed. Starting from commercial available styrenes, symmetrical 1,5-diarylpent-1-en-3-ones were produced in good to excellent yields (see scheme; dppp=1,3-bis(diphenylphosphino)propane). Copyright

Tandem Zn-Brook rearrangement/ene-allene carbocyclization

The addition of metalated alkynes to acylsilanes leads to the corresponding α-propargylsilanol derivatives. On addition of ZnBr2, Zn-promoted Brook rearrangements take place to produce the propargyl/allenylzinc bromides, which undergo cyclization to give functionalized carbocycles as single diastereoisomers. Wiley-VCH Verlag GmbH & Co. KGaA.

Lewis base-catalyzed conjugate reduction and reductive aldol reaction of α,β-unsaturated ketones using trichlorosilane

Lewis bases such as Ph3P=O and HMPA catalyze the 1,4-reduction of α,β-unsaturated ketones with trichlorosilane, and because the 1,2-reduction of aldehydes scarcely proceeded under the conditions, one-pot reductive aldol reactions with aldehydes were successfully achieved; preliminary studies using a chiral Lewis base revealed a high potential for enantioselective catalysis. The Royal Society of Chemistry.