88773-76-6

Upstream product

• 25308-75-2 1-Phenylcycloheptene 
• 81887-55-0 1-phenylcycloheptene epoxide 
• 176853-31-9 7,7-dimethoxy-7-phenylheptanal dimethyl acetal 
• 169892-12-0 (5E)-7-oxo-7-phenyl-hept-5-enal 
• 92101-56-9 7-hydroxy-7-phenylheptan-1-ol 
• 7472-43-7 6-benzoylhexanoic acid 
• 100-58-3 phenylmagnesium bromide 
• 2082-21-5 1-phenylcycloheptanol 

Downstream Products

• 18621-79-9 ((1S*,2S*)-2-hydroxycyclohexyl)(phenyl)methanone 
• 18621-79-9 (2-hydroxy-cyclopentyl)-phehyl-methanone 
• 1226854-91-6 C₃₀H₃₈O₃ 
• 263565-77-1 7-hydroxy-1-phenyl-heptan-1-one 

Relevant academic research and scientific papers

Controlling Chemoselectivity of Catalytic Hydroboration with Light

The ability to selectively react one functional group in the presence of another underpins efficient reaction sequences. Despite many designer catalytic systems being reported for hydroboration reactions, which allow introduction of a functional handle fo

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.

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage-Independent Activation of Strong C-O Bonds

Despite the prevalence of alcohols and carboxylic acids as functional groups in organic molecules and the potential to serve as radical precursors, C-O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen-centered nucleophile. We show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H atom trapping to afford the deoxygenated products. Using the same method, we demonstrate access to synthetically versatile acyl radicals, which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge C-O, C-N, and C-C bonds in a single step.

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.

TBD-catalyzed direct 5- and 6-enolexo aldolization of ketoaldehydes

Treatment of unfunctionalized acyclic ketoaldehydes with a catalytic amount of 1,5,7-triazabicyclo[4.4.0]dec-5-ene induces a direct intramolecular 5- and 6-enolexo aldolization, furnishing 2-ketocyclopentanols and 2-ketocyclohexanols in good-to-excellent yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Reductive generation of enolates from enones using elemental hydrogen: Catalytic C-C bond formation under hydrogenative conditions

Exposure of enones to elemental hydrogen in the presence of a Rh(I) catalyst enables reductive enolate generation, as evidenced by electrophilic trapping of the enolate by appendant and exogenous aldehyde partners. The significance of these findings resides in the ability to regioselectivity generate and transform transition metal enolates under catalytic conditions that circumvent formation of stoichiometric byproducts. Copyright

A new approach to arylaliphatic 1,5-, 1,6-, and 1,7-dicarbonyl compounds and their monoacetals based on direct anodic oxidation of 1-phenyl- and benzo[c]cycloalkenes

A new simple approach to ω-benzoylalkanals, 2-(ω-formylalkyl)benzaldehydes, and their monoacetals was developed based on direct anodic oxidation of 1-phenylcycloalkenes and benzo[c]cycloalkenes in methanol followed by acid hydrolysis of the electrolysis p

Ring size effect in oxidation of 1-phenylcycloalkenes with chromic anhydride-pyridine complex: Preferential formation of epoxide with increase in ring size

A marked ring size effect in the oxidation of 1-phenylcycloalkenes (1) with chromic anhydride-pyridine complex has been observed.While 1-phenylcyclopentene (1a) and 1-phenylcyclohexene (1b) give the expected α,β-unsaturated cyclic ketones (2a,b) 1-phenylcycloheptene (1c) and 1-phenylcyclooctene (1d) furnish epoxides (5c,d) as the major products.