Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates

Tao, Minglin; Feng, Qin; Gong, Kaixing; Yang, Xuege; Shi, Lou; Chang, Qiaowen; Liang, Deqiang

doi:10.1039/d4gc00352g

Cited by 15 publications

(1 citation statement)

References 158 publications

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“…The reaction types are quite limited, and probably because PC loss occurs during electrolysis, [9c,10c,11d] the use of a more or less high loading of a PC, which might be expensive, is generally required. Thus, it is highly desirable and imperative to develop new electrophotocatalytic archetypes, [21] especially strategies with a low PC loading or even under PC-free conditions.…”

Section: Introductionmentioning

confidence: 99%

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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Section: Introductionmentioning

confidence: 99%

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

Gong,

Ma,

et al. 2024

Adv Synth Catal

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Photocatalyzed Acylmethylation/Cyclization of Unactivated Alkenes with Sulfoxonium Ylides towards Acylmethylated Polycyclic Quinazolinones

Wu,

Liu,

et al. 2024

ChemCatChem

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The synthesis of acylmethylatated pyrrolo‐quinazolinones was developed via photo‐induced cascade radical addition/cyclization of N‐(but‐3‐enyl)quinazolin‐4(3H)‐ones with sulfoxonium ylides using 4CzIPN as the photocatalyst. This approach was also suitable for the construction of acylmethylatated piperidino‐quinazolinones. This protocol features with mild conditions, convenient operation, broad substrate scope and good functional group compatibility.

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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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Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates

Abstract: Both the polycyclic pyrimidin-4-one synthesis and the dehydrogenative coupling of malonates often enough require a redox agent, an elevated temperature, large amounts of transition-metal salts, and/or highly acidic/basic conditions, and...

Cited by 15 publications

References 158 publications

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

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

Photocatalyzed Acylmethylation/Cyclization of Unactivated Alkenes with Sulfoxonium Ylides towards Acylmethylated Polycyclic Quinazolinones

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

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