32363-56-7

Upstream product

• 54120-34-2 trans-1,2-dibenzoylcyclobutane 
• 109976-51-4 6-Phenyl-hex-5-en-saeure-ethylester 
• 14660-52-7 ethyl 5-bromovalerate 
• 3375-38-0 1,4-dibenzoylbutane 
• 75424-63-4 5-oxo-5-phenylpentanal 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 29526-96-3 1-phenylcyclopropan-1-ol 
• 124517-47-1 cinnamyl tert-butyl carbonate 
• 444575-79-5 carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 100-42-5 styrene 
• 98-86-2 acetophenone 
• 13466-32-5 acetophenone dimethylhydrazone 
• 1393823-55-6 2-cyclohexyl-3-(pent-4'-en-1'-yl)-3-phenyl-1,2-oxaziridine 

Downstream Products

• 84-15-1 o-terphenyl 

Relevant academic research and scientific papers

Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate

We report herein a nickel-catalyzed ring-opening allylation of cyclopropanols with allylic carbonates that occurs under mild and neutral conditions. The reaction displays linear selectivity for both linear and branched acyclic allylic carbonates and is also applicable to cyclic allylic carbonates, affording a variety of δ,?-unsaturated ketones in moderate to good yields. Mechanistic experiments are in accord with a catalytic cycle involving decarboxylative oxidative addition of allylic carbonate to Ni(0), alkoxide exchange with cyclopropanol, cyclopropoxide-to-homoenolate conversion on Ni(II), and C-C reductive elimination.

Diastereoselective and Stereodivergent Synthesis of 2-Cinnamylpyrrolines Enabled by Photoredox-Catalyzed Iminoalkenylation of Alkenes

A photoredox-catalyzed iminoalkenylation of γ-alkenyl O-acyl oximes has been developed. Readily available alkenylboronic acids serve as alkenylation reagents, leading to densely functionalized pyrrolines. Both (E)- and (Z)-cinnamylpyrrolines are accessible depending on the reaction solvent. In dichloromethane, (E)-cinnamylpyrrolines are produced through a photoredox-mediated single-electron-transfer process. In tetrahydrofuran, (Z)-cinnamylpyrrolines are generated by photocatalytic contra-thermodynamic E-to-Z isomerization of (E)-cinnamylpyrrolines though an energy-transfer pathway. Two stereocenters are established with complete diastereoselectivity and only one diastereomer is isolated.

Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature

It is reported that Pd(PPh3)2Cl2 in combination with 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) under irradiation of blue LEDs efficiently catalyzes a decarboxylative Heck reaction of vinyl arenes and vinyl heteroarenes with aliphatic N-(acyloxy)phthalimides at room temperature. A broad scope of secondary, tertiary, and quaternary carboxylates, including α-amino acid derived esters, can be applied as amenable substrates with high stereoselectivity. The experimental observation was explained by excitation-state reactivity of the palladium complex under irradiation to induce single-electron transfer to activate N-(acyloxy)phthalimides, and to suppress undesired β-hydride elimination of alkyl palladium intermediates.

Copper-catalyzed oxaziridine-mediated oxidation of C-H bonds

The highly regio- and chemoselective oxidation of activated C-H bonds has been observed via copper-catalyzed reactions of oxaziridines. The oxidation proceeded with a variety of substrates, primarily comprising allylic and benzylic examples, as well as one example of an otherwise unactivated tertiary C-H bond. The mechanism of the reaction is proposed to involve single-electron transfer to the oxaziridines to generate a copper-bound radical anion, followed by hydrogen atom abstraction and collapse to products, with regeneration of the catalyst by a final single-electron transfer event. The involvement of allylic radical intermediates was supported by a radical-trapping experiment with TEMPO.

Titanocene(III) chloride mediated reductive cleavage of arylcyclopropyl ketones

Titanocene(III) chloride (Cp2TiCl) mediated cleavage of arylcyclopropyl ketones has been accomplished. Both saturated and β-H eliminated unsaturated aromatic compounds are formed in different ratio depending on the substrate. Ti(III) species has been prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and zinc dust in THF.

Synthesis of hexahydrocyclopenta[c]furans by an intramolecular iron-catalyzed ring expansion reaction

The intramolecular iron-catalyzed ring expansion reaction of epoxyalkenes was investigated with a preformed iron(salen) [Fe(Salen)] complex. The formal insertion of the alkene into the epoxide generated hexahydrocyclopenta[c]furan derivatives in moderate to good yields and diastereoselectivities depending on other functional groups present in the starting materials. In addition, oxygen-tethered epoxyalkenes were used for the synthesis of lignan isomers. The scope and limitations of the Fe (Salen)-catalyzed process of the reaction are discussed.

Iron-salen complexes as efficient catalysts in ring expansion reactions of epoxyalkenes

The optimisation of the iron-catalysed ring expansion reaction of epoxyalkenes was considerably improved when the original phosphine ligand system [FeCl2(dppe)] was altered to include nitrogen-containing ligand systems. Especially, the very pot

Zinc-promoted reactions. 8. The effect of ring strain in the reduction of 1,2-dibenzoylcycloalkanes

Ring cleavage was the main route in the Zn reduction of 1 in neat AcOH, while selective carbonyl reduction predominated in the presence of LiCl. The less strained 2 underwent only carbonyl reduction with Zn/AcOH. The Clemmensen reduction of both 1 and 2 resulted mainly in acyclic products. The unstrained 3 was fairly resistant towards reduction, and did not undergo ring cleavage.

AN IMPROVED METHOD FOR THE GENERATION OF ORGANOZINC CARBENOIDS AND ITS APLLICATION IN DICARBONYL COUPLING REACTIONS

Reaction of aromatic aldehydes and certain α,β-unsatured carbonyl compounds with 1,2-bis(chlorodimethylsilyl)ethane and zinc leads to products of symmetrical dicarbonyl coupling. Key words: Dicarbonyl Coupling; 1,2-bis(chlorodimethylsilyl)ethane and Zinc