69573-42-8

Upstream product

• 942-93-8 5-Chloro-1-phenyl-1-pentanone 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 4144-62-1 5-benzoylvaleric acid 
• 700-88-9 cyclopentylbenzene 
• 3240-29-7 1-Phenylpent-4-en-1-one 
• 4509-91-5 5-bromo-1-phenyl-1-pentanone 
• 10487-96-4 1-phenylcyclopentanol 
• 67888-71-5 N-(1-phenylethylidene)cyclohexylamine 
• 13466-32-5 acetophenone dimethylhydrazone 

Downstream Products

• 57050-07-4 2-phenyl-3,4,5,6-tetrahydropyridine 
• 227937-21-5 (Z)-(5-azido-1-phenylpent-1-enyloxy)(tert-butyldimethyl)silane 
• 10413-00-0 5-oxo-5-phenylpentanenitrile 
• 227937-23-7 (S)-(-)-5-azido-2-hydroxy-1-phenylpentan-1-one 
• 227937-24-8 (R)-(-)-5-azido-2-hydroxy-1-phenylpentan-1-one 
• 148701-46-6 cis-(3S)-hydroxy-(2S)-phenylpiperidine 
• 3389-54-6 n-benzoylpyrrolidine 

Relevant academic research and scientific papers

Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones

A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been presented. A variety of cycloalkanones with varying ring sizes and various α-substituents reacted well to give the distal keto acids or dicarboxylic acids with moderate to good yields.

The Formation of C-C or C-N Bonds via the Copper-Catalyzed Coupling of Alkylsilyl Peroxides and Organosilicon Compounds: A Route to Perfluoroalkylation

The copper-catalyzed selective cleavage of alkylsilyl peroxides and the subsequent formation of carbon-carbon or carbon-nitrogen bonds with organosilicon compounds are described. The reaction proceeds under mild conditions and exhibits a broad substrate scope with respect to both cyclic and acyclic alkylsilyl peroxides in combination with carbon and nitrogen sources. In particular, this approach enables the facile radical perfluoroalkylation using commercially available perfluoroalkyltrimethylsilanes. Our mechanistic studies suggest that the reaction should proceed via a free-radical process.

In-situ-generation of alkylsilyl peroxides from alkyl hydroperoxides and their subsequent copper-catalyzed functionalization with organosilicon compounds

Alkylsilyl peroxides were generated in situ from the corresponding alkyl hydroperoxides using organosilicon compounds of the type Me3SiX (X = CN, N3, and halogens) and an amine base. Subsequent in situ copper-catalyzed homolytic cleavage of the alkylsilyl peroxides afforded alkyl radicals, which were then trapped with X (X = CN, N3, and halogens) to furnish products with new carbon-carbon, carbon-nitrogen, or carbon-halogen bonds in good to high 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.

Anti-Markovnikov Hydroazidation of Alkenes by Visible-Light Photoredox Catalysis

The anti-Markovnikov hydroazidation of alkenes has been accomplished under visible-light irradiation by using [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as the photocatalyst and trimethylsilyl azide as the azidating agent. The reactions were greatly facilitated by water, the beneficial effect of which can be attributed to its participation in the reaction as the hydrogen donor, as indicated by deuterium isotope experiments. The reactions proceed under solvent free conditions in the presence of water. 4-Dimethylaminopyridine also exhibited a beneficial effect on the reactions. The present method enabled hydroazidation of several types of unactivated alkenes with good yields and high regioselectivity.

Visible light-promoted ring-opening functionalization of unstrained cycloalkanols via inert C-C bond scission

Described herein is a novel, useful, visible light-promoted ring-opening functionalization of unstrained cycloalkanols. Upon scission of an inert cyclic C-C σ-bond, a set of medium- and large-sized rings are readily brominated under mild reaction conditio

La reaction d'ω-azidocetones avec la triphenylphosphine: une voie d'acces generale aux imines cycliques

The ω-azidoketones RC(=O)-CH(R')-(CH2)n-CH(R'')-N3 react with triphenylphosphine in anhydrous media to give 5, 6 and 7 membered cyclic imines via an intramolecular aza-Wittig reaction with good yields.A general synthesis of ω-haloketones which are the precursors of the azidoketones was also devised.