87258-30-8

Upstream product

• 771-98-2 1-Phenylcyclohexene 
• 17851-49-9 5-hydroxypentyl phenyl ketone 
• 176853-30-8 6,6-dimethoxy-6-phenylhexanal dimethyl acetal 
• 56721-39-2 δ-benzoylvaleric acid chloride 
• 4144-62-1 5-benzoylvaleric acid 
• 4066-82-4 1-phenyl-hexane-1,6-diol 
• 1589-60-2 1-phenylcyclohexanol 
• 108-94-1 cyclohexanone 
• 100-58-3 phenylmagnesium bromide 
• 827-52-1 1-phenyl-1-cyclohexane 
• 20614-61-3 cyclohexyl-1-phenyl-1-hydroperoxide 
• 10487-96-4 1-phenylcyclopentanol 
• 825-54-7 cyclopent-1-en-1-ylbenzene 
• 120-92-3 cyclopentanone 

Downstream Products

• 97346-33-3 6-hydroxy-1-phenyl-8-nonen-1-one 
• 15177-05-6 1-phenylhept-6-en-1-one 
• 123027-25-8 2-phenyl-1,7-octadiene 
• 4066-82-4 1-phenyl-hexane-1,6-diol 
• 32346-66-0 (±)-2-hydroxycyclopentyl(phenyl)methanone 
• 32346-66-0 (2-hydroxy-cyclopentyl)-phenyl-methanone 
• 1026732-62-6 ethyl (E)-8-oxo-8-phenyloct-2-enoate 
• 1222087-99-1 (8E)-1,9-diphenylnona-6,8-dien-1-one 
• 1313885-32-3 6-cyclopentenyl-1-phenylhex-5-yn-1-one 
• 15447-62-8 1-phenyl-hex-5-yn-1-one 
• 87258-32-0 ethyl 3-hydroxy-8-phenyl-8-oxooctanoate 
• 87258-31-9 3-Hydroxy-8-oxo-3-phenyl-octanoic acid ethyl ester 
• 97364-14-2 6-hydroxy-1-phenyl-7-(phenylsulfonyl)heptanone 
• 97364-13-1 6-hydroxy-1-phenyl-1-heptanone 

Relevant academic research and scientific papers

A copper(II)-mediated regioselective cyclization-acetoxylation of 6,8-Dien-1-ones for the synthesis of functionalized cyclopentanes

This paper describes a copper(II) acetate-mediated cyclization- acetoxylation of 6,8-dien-1-ones in the presence of sodium acetate as base. A variety of functionalized cyclopentanes containing synthetic useful allylic alcohol moieties with three contiguou

Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity

Aerobic alcohol oxidations catalyzed by transition metal salts and aminoxyls are prominent examples of cooperative catalysis. Cu/aminoxyl catalysts have been studied previously and feature "integrated cooperativity", in which CuII and the aminoxyl participate together to mediate alcohol oxidation. Here we investigate a complementary Fe/aminoxyl catalyst system and provide evidence for "serial cooperativity", involving a redox cascade wherein the alcohol is oxidized by an in situ-generated oxoammonium species, which is directly detected in the catalytic reaction mixture by cyclic step chronoamperometry. The mechanistic difference between the Cu- and Fe-based catalysts arises from the use iron(III) nitrate, which initiates a NOx-based redox cycle for oxidation of aminoxyl/hydroxylamine to oxoammonium. The different mechanisms for the Cu- and Fe-based catalyst systems are manifested in different alcohol oxidation chemoselectivity and functional group compatibility.

Iron-catalyzed chemoselective hydride transfer reactions

A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.

Iodobenzene-catalyzed oxidative cleavage of olefins to carbonyl compounds

A metal-free approach for the oxidative cleavage of carbon–carbon double bonds of olefins to carbonyl compounds was established by using oxidant m-CPBA and non-metallic organocatalyst PhI in toluene/H2O. A broad scope of aromatic olefins was used. All the reactions proceeded smoothly at 35 °C in short reaction time to furnish the respective mono- and double carbonyl compounds selectively in moderate to good yields.

Visible-light-promoted site-specific and diverse functionalization of a c(sp3)-c(sp3) bond adjacent to an arene

We report here a strategy for inert C-C bond functionalization. Site-specific cleavage and functionalization of a saturated C(sp3)-C(sp3) bond via a visible-light-induced radical process have been achieved. The general features of this reaction are as follows. (1) Both linear and cyclic C(sp3)-C(sp3) bonds with a vicinal arene can be specifically functionalized. (2) One carbon is converted into a ketone, and another can be tunably converted into nitrile, peroxide, or halide. (3) The typical conditions include 1.0 mol % of Ru(bpy)3Cl2, 1.0 or 5.0 equiv of Zhdankin reagent, white CFL (24 W), open flask, and room temperature. These reactions offer powerful tools to modify carbon skeletons that are intractable by conventional methods. Good selectivity and functional group tolerance, together with mild and open air conditions, make these transformations valuable and attractive.

Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes

The direct reduction of carboxylic acids to aldehydes is a fundamental transformation in organic synthesis. The combination of an air-stable Ni precatalyst, dimethyl dicarbonate as an activator, and silane reductant effects this reduction for a wide variety of substrates, including pharmaceutically relevant structures, in good yields and with no overreduction to alcohols. Moreover, this methodology is scalable, allows access to deuterated aldehydes, and is also compatible with one-pot utilization of the aldehyde products.

Room-Temperature Chemoselective Reductive Alkylation of Amines Catalyzed by a Well-Defined Iron(II) Complex Using Hydrogen

A transition-metal frustrated Lewis pair approach has been envisaged to enhance the catalytic activity of tricarbonyl phosphine-free iron complexes in reduction of amines. A new cyclopentadienyl iron(II) tricarbonyl complex has been isolated, fully characterized, and applied in hydrogenation. This phosphine-free iron complex is the first Earth-abundant metal complex that is able to catalyze chemoselective reductive alkylation of various functionalized amines with functionalized aldehydes. Such selectivity and functionality tolerance (alkenes, esters, ketones, acetals, unprotected hydroxyl groups, and phosphines) have been demonstrated also for the first time at room temperature with an Earth-abundant metal complex. This alkylation reaction was also performed without any preliminary condensation and generated only water as a byproduct. The resulting amines provided rapid access to potential building blocks, metal ligands, or drugs. Density functional theory calculations highlighted first that the formation of the 16 electron species, via the activation of the tricarbonyl complex Fe3, was facilitated and, second, that the hydrogen cleavage did not follow the same pathway as bond breaking, usually described with the known cyclopentadienone iron tricarbonyl complexes (Fe1 and Fe4). These calculations highlighted that the new complex Fe3 does not behave as a bifunctional catalyst, in contrast to its former congeners.

Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O2

A mild and operationally simple iron-catalyzed protocol for the selective aerobic oxidation of aromatic olefins to carbonyl compounds is described. Catalyzed by a Fe(III) species bearing a pyridine bisimidazoline ligand at 1 atm of O2, α- and β-substituted styrenes were cleaved to afford benzaldehydes and aromatic ketones generally in high yields with excellent chemoselectivity and very good functional group tolerance, including those containing radical-sensitive groups. With α-halo-substituted styrenes, the oxidation took place with concomitant halide migration to afford α-halo acetophenones. Various observations have been made, pointing to a mechanism in which both molecular oxygen and the olefinic substrate coordinate to the iron center, leading to the formation of a dioxetane intermediate, which collapses to give the carbonyl product. (Chemical Equation).

Development of an azanoradamantane-type nitroxyl radical catalyst for class-selective oxidation of alcohols

The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.

Oxidations of alkenes with hypervalent iodine reagents: An alternative ozonolysis of phenyl substituted alkenes and allylic oxidation of unsubstituted cyclic alkenes

Unsaturated CC double bonds with a phenyl substituent can be cleaved with iodylbenzene and iodosylbenzene to give carbonyl compounds. It is believed that the reactions occur via a radical pathway. The allylic oxidation of cyclic alkenes lacking a phenyl substituent was achieved in acetonitrile/water mixture (3:1) also using iodylbenzene and iodosylbenzene.