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Upstream product

• 7006-52-2 3-chloro-N-methylaniline 
• 920-46-7 Methacryloyl chloride 
• 108-42-9 3-chloro-aniline 
• 2918-71-0 N-(3-chlorophenyl)methacrylamide 
• 74-88-4 methyl iodide 

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.

Synthesis of Dichlorocyanomethyl-Functionalized Oxindoles by Cascade Reactions Initiated by Copper(I)-Catalytically Generated Dichlorocyanomethyl Radical

An efficient and convenient protocol for synthesis of dichlorocyanomethyl-functionalized oxindoles through the cascade reactions of dichlorocyanomethyl radical with N-arylacrylamides is reported. The electrophilic dichlorocyanomethyl radical, which is gen

Synthesis of hydroxyl-containing oxindoles and 3,4-dihydroquinolin-2-ones through oxone-mediated cascade arylhydroxylation of activated alkenes

Hydroxyl-containing compounds are highly value-Added organic molecules, and the establishment of novel methodologies for their elaboration is a long-standing challenge in organic synthesis. Here the first oxone-mediated direct arylhydroxylation of activat

Nickel-Catalyzed Transformation of Diazoacetates to Alkyl Radicals Using Alcohol as a Hydrogen Source

A nickel-catalyzed transformation of diazoacetates to α-carbonyl methylene radicals has been disclosed in the presence of hyperoxide using ethanol as a hydrogen source and solvent. This strategy is successfully applied in the formation of indolin-2-ones or 1,4-dicarbonyl compounds from acrylamides or enamides in moderate to good yields. These reactions undergo radical addition onto C-C double bonds followed by a cyclization/oxidation or an oxidation/hydrolysis process, respectively.

Iron-Catalyzed Synthesis of Oxindoles: Application to the Preparation of Pyrroloindolines

A novel and highly efficient synthetic approach to pyrroloindolines has been developed. The process is based on tandem radical addition/cyclization with inexpensive iron catalyst. This method tolerates a wide range of N-methyl-N-arylacrylamides as well carbamoyl radicals, providing access to a variety of functionalized 3,3-disubstituted oxindoles, key intermediates for many bioactive pyrroloindolines such as (±)-esermethole, (±)-deoxyeseroline, and (±)-physovenol methyl ether.

UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions

UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.