1643771-79-2

Upstream product

• 15796-89-1 N-methyl-N-phenylmethacrylamide 
• 99-91-2 para-chloroacetophenone 
• 1611-83-2 2-methyl-N-phenylacrylamide 
• 62-53-3 aniline 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Relevant academic research and scientific papers

Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals

A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.

Microwave-Assisted Copper-Catalyzed Oxidative Cyclization of Acrylamides with Non-Activated Ketones

An operationally simple and efficient microwave-assisted protocol for the oxidative cyclization of acrylamide derivatives with non-activated ketones to generate 3,3-disubstituted oxindoles is described. The reaction proceeds by a copper-catalyzed tandem radical addition/cyclization strategy and tolerates a series of functional groups with moderate to excellent yields. From a kitchen to the lab! An efficient Cu-catalyzed microwave-assisted oxidative addition of non-activated ketones to acrylamides is described for the construction of 3,3-disubstituted oxindoles (see scheme). This simple transformation demonstrates a high functional group tolerance, providing good to excellent product yields under mild reaction conditions.

Palladium-catalyzed oxidative difunctionalization of alkenes with α-carbonyl alkyl bromides initiated through a heck-type insertion: A route to indolin-2-ones

The oxidative interception of various σ-alkyl palladium(II) intermediates with additional reagents for the difunctionalization of alkenes is an important research area. A new palladium-catalyzed oxidative difunctionalization reaction of alkenes with α-carbonyl alkyl bromides is described, in which the σ-alkyl palladium(II) intermediate is generated through a Heck insertion and trapped using an aryl C(sp2)-H bond. This method can be applied to various α-carbonyl alkyl bromides, including primary, secondary, and tertiary α-bromoalkyl esters, ketones, and amides. Indolinone synthesis: A new palladium-catalyzed oxidative difunctionalization reaction of N-arylalkenes with primary, secondary, and tertiary α-carbonyl alkyl bromides proceeds through a radical process and provides indolin-2-ones in moderate to excellent yields. The reaction is initiated by a Heck insertion followed by interception of the σ-alkyl palladium(II) intermediate with aryl C(sp2)-H bonds. dppe=1,2-bis(diphenylphosphino)ethane.