51758-25-9

Upstream product

• 13159-16-5 5-phenyl-4-penten-1-ol 
• 1198-34-1 2-Phenylcyclopentanone 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 98678-26-3 2-Benzylcyclobutan-1-one 
• 13466-40-5 5-phenylpenta-2,4-dienal 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 5390-04-5 pent-1-yn-5-ol 
• 591-50-4 iodobenzene 

Downstream Products

• 126976-43-0 (Z)-7-Phenyl-hept-6-en-1-yn-3-one 
• 126976-37-2 (E)-7-Phenyl-hept-6-en-1-yn-3-one 
• 126976-41-8 3-Benzyl-2-methylene-cyclopentanone 
• 895540-03-1 (Z)-2-(4-phenylbut-3-en-1-yl)oxirane 
• 895540-88-2 (E)-2-(4-phenylbut-3-en-1-yl)oxirane 
• 1315320-16-1 C₂₅H₃₁N₃O₆ 
• 1315320-15-0 C₁₇H₁₇NO₂ 

Relevant academic research and scientific papers

Fused-Ring Formation by an Intramolecular “Cut-and-Sew” Reaction between Cyclobutanones and Alkynes

The development of a catalytic intramolecular “cut-and-sew” transformation between cyclobutanones and alkynes to construct cyclohexenone-fused rings is described herein. The challenge arises from the need for selective coupling at the more sterically hind

Stable gold(III) catalysts by oxidative addition of a carbon-carbon bond

Low-valent late transition-metal catalysis has become indispensable to chemical synthesis, but homogeneous high-valent transition-metal catalysis is underdeveloped, mainly owing to the reactivity of high-valent transition-metal complexes and the challenges associated with synthesizing them. Here we report a carbon-carbon bond cleavage at ambient conditions by a Au(i) complex that generates a stable Au(iii) cationic complex. In contrast to the well-established soft and carbophilic Au(i) catalyst, this Au(iii) complex exhibits hard, oxophilic Lewis acidity. For example, we observed catalytic activation of α,β-unsaturated aldehydes towards selective conjugate additions as well as activation of an unsaturated aldehyde-allene for a [2 + 2] cycloaddition reaction. The origin of the regioselectivity and catalytic activity was elucidated by X-ray crystallographic analysis of an isolated Au(iii)-activated cinnamaldehyde intermediate. The concepts revealed suggest a strategy for accessing high-valent transition-metal catalysis from readily available precursors.

HYDROGENATION OF DIENALS WITH RHODIUM COMPLEXES UNDER CARBON MONOXIDE FREE ATMOSPHERE

The present invention relates to the field of catalytic hydrogenation and, more particularly, to a process for the reduction by hydrogenation, using molecular H2, of a C6-C20 conjugated dienal into the corresponding deconjugated enal, characterized in that said process is carried out in the presence of a catalytic system comprising at least a base and at least one complex in the form of a rhodium complex comprising a C34-C60 bidentate diphosphine ligand (L2) coordinating the rhodium.

HYDROGENATION OF DIENALS WITH RHODIUM COMPLEXES UNDER CARBON MONOXIDE FREE ATMOSPHERE

The present invention relates to the field of catalytic hydrogenation and, more particularly, to a process for the reduction by hydrogenation, using molecular H2, of a C6-C20 conjugated dienal into the corresponding deconjugated enal, characterized in that said process is carried out in the presence of a catalytic system comprising at least a base and at least one complex in the form of a rhodium complex comprising a C34-C60 bidentate diphosphine ligand (L2) coordinating the rhodium.

Metal-free oxyaminations of alkenes using hydroxamic acids

A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.

Palladium-catalyzed reactions of 3-substituted methylenecyclopropanes

Pd-catalyzed reactions of 3-substituted methylenecyclopropanes (MCPs), in which the substituents can be either hydroxymethyl or formyl, have been thoroughly investigated in the presence or absence of an acid source. It was found that the Pd-catalyzed reactions of methylenecyclopropylcarbinols (Z)-1 in the presence of acetic acid, acetic acid 2-methylene-but-3-enyl esters 4 can be formed in moderate yields. It was also found that Pd alone can catalyze the isomerization of methylenecyclopropylcarbinols (E)-1 in the absence of an acid source to form pent-4-enals 3. The Pd-catalyzed reactions of methylenecyclopropanecarbaldehydes 5 were also carried out in the presence of acetic acid. It was found that when (E)-5 was used as the substrate, the isomerized product, penta-2,4-dienal 6, could be obtained in good to high yields, whereas the use of (Z)-5 gave 2-(3-formylpenta-2,4-dienylidene) cyclopropanecarbaldehyde 7 in moderate to good yields. Plausible mechanisms for all these transformations have been discussed on the basis of the obtained results and control experiments. Copyright

Dioxime oxalates; new iminyl radical precursors for syntheses of N-heterocycles

Symmetrical and unsymmetrical dioxime oxalates were prepared by treatment of oximes with oxalyl chloride. UV photolysis of these precursors was found to be an atom-efficient way of generating iminyl radicals. The process was most efficient for dioxime oxalates having aryl substituents attached to their C{double bond, long}N bonds. The method was useful for EPR spectroscopic study of iminyl and iminoxyl radicals. Photolyses in toluene solution, of dioxime oxalates containing alkenyl acceptor groups, yielded unsaturated iminyl radicals that ring closed to afford 3,4-dihydro-2H-pyrroles in good yields. Dioxime oxalates with biphenyl substituents also released iminyl radicals that ring closed onto the aromatic acceptor groups and, in acetonitrile solution, this approach provided a useful and atom-efficient method of making substituted phenanthridines.

Two-photon generation of the 1,4-diphenyl-1,4-butanediyl biradical: Direct detection and product studies

The 1,4-diphenyl-1,4-butanediyl biradical (3) is generated from 1,4- dichloro-1,4-diphenylbutane (1) or 2,5-diphenylcyclopentanone (8) under several irradiation conditions. The products resulting from this intermediate are styrene (4), 1,2-diphenylcyclobutane (5), and 1-phenyl-1,2,3,4- tetrahydronaphthalene (6). The formation of tetrahydronaphthalenes appears to be a fingerprint for the intermediacy of 1,4-biradicals having a phenyl group attached to one of the radical centers as corroborated in the high-intensity irradiation of 2-phenylcyclopentanone (12). The yield of 6 depends on the substrate and irradiation conditions; this is rationalized as due to a conformational memory effect of the nascent biradical.

Intramolecular cyclization of acetylenic homoallylic ketones mediated by the addition of stannyl radicals; a short facile pathway to α-methylene-β-substituted cyclopentanones

α-(Stannyl)methylenecyclopentanones are obtained by tributylstannane addition reactions of acetylenic homoallylic ketones. α-Methylenecyclopentanones are produced upon destannylation.