Synthesis of Diverse 4‐Pyrrolin‐2‐ones by Electrochemically Induced Dehydrogenative Regioselective Cyclization of 3‐Aza‐1,5‐dienes and 1,3‐Dicarbonyl Compounds

Ji, Xing; He, Run; Shi, Lou; Sun, Shaoguang; Liang, Deqiang

doi:10.1002/ejoc.202301246

Eur J Org Chem

2024

DOI: 10.1002/ejoc.202301246

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Synthesis of Diverse 4‐Pyrrolin‐2‐ones by Electrochemically Induced Dehydrogenative Regioselective Cyclization of 3‐Aza‐1,5‐dienes and 1,3‐Dicarbonyl Compounds

Xing Ji,

Run He,

Lou Shi

et al.

Abstract: A practical and mild electrochemical dehydrogenative regioselective cyclization method has been established for the synthesis of 4‐pyrrolin‐2‐ones using 3‐aza‐1,5‐dienes and 1,3‐dicarbonyl compounds as substrates. This protocol is catalyst‐free, metal‐free, and does not require oxidizing agents. It exhibits wide substrate compatibility and can be easily scaled up to the gram scale.

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Cited by 9 publications

References 88 publications

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Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes

Gong,

Ma,

et al. 2024

Adv Synth Catal

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While the emergence of electrophotochemistry provides opportunities, such a chemistry at this stage suffers from limited reaction types and high photocatalyst loadings. A self‐catalyzed electrophotosynthesis as well as one with a low photocatalyst loading is presented. These external‐oxidant‐free cyclizations are enabling and applicable to a range of activated alkenes, affording a diverse array of thiocyanato heterocycles including 4‐pyrrolin‐2‐ones, isoquinoline‐1,3‐diones, indolo[2,1‐a]isoquinolin‐6(5H)‐ones, benzoimidazo[2,1‐a]isoquinolin‐6(5H)‐ones and indolin‐2‐ones, and the protocols are amenable to the late‐stage diversification of complex molecular architectures as well as gram‐scale syntheses. Sunlight could serve as the light source, and the reaction could be conducted in an all‐solar‐driven mode using a commercially available photovoltaic panel to produce electricity.

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Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes

Gong,

Ma,

et al. 2024

Adv Synth Catal

Self Cite

View full text Add to dashboard Cite

show abstract

Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide

Wang,

Zeng,

Shi

et al. 2024

Chemistry A European J

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Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N‐hydroxyphthalimide catalyst, respectively, are presented for the selenylation/cyclization of the fragile substrates of 3‐aza‐1,5‐dienes with diorganyl diselenides to afford 3‐selenomethyl‐4‐pyrrolin‐2‐ones. The two electrophotocatalytic reactions and the indirect electrolysis one are both regioselective and external‐oxidant‐ and transition‐metal‐free, and are associated with a broad substrate scope and high Se‐economy, and all three methods are amenable to gram‐scale syntheses, late‐stage functionalizations, sunlight‐induced experiments and all‐solar‐driven syntheses.

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DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes

Ding,

Yang,

Luo

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryHerein, we report a rare example of three‐component net‐oxidative sulfonylation of a SO2 surrogate with an oxidatively activated radical precursor under mild and metal‐ and external‐oxidant‐free conditions. The mildness and sustainability of the reaction are enabled by photoelectrocatalysis, and 3‐aza‐1,5‐dienes, organotrifluoroborates and 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in an atom‐economical manner with a broad substrate scope and good functional‐group tolerance. The protocol is amenable to the late‐stage diversification of complex molecular architectures as well as the gram‐scale synthesis. Sunlight could be used as the light source, and the reaction could be conducted in an all‐solar mode using a commercially available photovoltaic panel to generate electricity in situ. Mechanistic studies reveal that the in situ generated 1,4‐diazabicyclo[2.2.2]octane (DABCO), which was generally innocent in previous reactions, functions as an electron shuttle between the photocatalytic cycle and the reactants.

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Synthesis of Diverse 4‐Pyrrolin‐2‐ones by Electrochemically Induced Dehydrogenative Regioselective Cyclization of 3‐Aza‐1,5‐dienes and 1,3‐Dicarbonyl Compounds

Cited by 9 publications

References 88 publications

Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes

Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes

Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide

DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes

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