Iron-catalyzed radical intermolecular addition of unactivated alkenes to alkenyl N-heteroarenes

Reductive radical dearomatization N-alkyl quinoline quaternary ammonium salts to synthesize structurally complex and challenging polysubstituted benzo [d][1,3]oxazocines was first reported. The mechanism showed various allyl alcohols can be converted into alkyl radicals under reduction conditions of iron/silane. These radicals then nucleophilically attack the C4 site of Nalkyl quinoline quaternary ammonium salts, and intramolecular cyclization of the resulting intermediate generates the target product. This method not only produced a series of novel polysubstituted benzo [d][1,3]oxazocines but also prepared polycyclic benzo [d][1,3]oxazocines. Finally, this strategy made up for the lack of reductive radical reports on N-alkylquinolinium salts and also had the advantages of mild reaction conditions, wide substrate range, and novel product structure.

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Ferrocene catalyzed carbohydroxylation of alkenes using H₂O and cycloketone oxime esters

Ajmeera,

Golagani,

Akondi

2023

Org. Biomol. Chem.

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Iron-catalyzed radical intermolecular addition of unactivated alkenes to alkenyl N-heteroarenes

Abstract: The intermolecular reductive radical coupling of olefins with alkenyl N-heteroarenes, employing an iron(III)-catalyzed hydrogen atom transfer strategy, is described. The important practical features are the use of a cheap catalytic...

Cited by 5 publications

References 83 publications

Nickel-Catalyzed Three-Component Alkylarylation of Alkenyl N-Heteroarenes

Nickel-Catalyzed Three-Component Alkylarylation of Alkenyl N-Heteroarenes

Facile Construction of Benzo[d][1,3]oxazocine: Reductive Radical Dearomatization of N-Alkyl Quinoline Quaternary Ammonium Salts

Ferrocene catalyzed carbohydroxylation of alkenes using H₂O and cycloketone oxime esters

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Iron-catalyzed radical intermolecular addition of unactivated alkenes to alkenyl N-heteroarenes

Abstract: The intermolecular reductive radical coupling of olefins with alkenyl N-heteroarenes, employing an iron(III)-catalyzed hydrogen atom transfer strategy, is described. The important practical features are the use of a cheap catalytic...

Cited by 5 publications

References 83 publications

Nickel-Catalyzed Three-Component Alkylarylation of Alkenyl N-Heteroarenes

Nickel-Catalyzed Three-Component Alkylarylation of Alkenyl N-Heteroarenes

Facile Construction of Benzo[d][1,3]oxazocine: Reductive Radical Dearomatization of N-Alkyl Quinoline Quaternary Ammonium Salts

Ferrocene catalyzed carbohydroxylation of alkenes using H2O and cycloketone oxime esters

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Ferrocene catalyzed carbohydroxylation of alkenes using H₂O and cycloketone oxime esters