Photoredox-Catalyzed Synthesis of 3-Sulfonylated Pyrrolin-2-ones via a Regioselective Tandem Sulfonylation Cyclization of 1,5-Dienes

Ding, Ran; Zhang, Lipeng; Yu, Yi‐Tao; Zhang, Bing; Wang, Pei-Long

doi:10.3390/molecules28145473

Cited by 5 publications

(1 citation statement)

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“…However, the reaction changing from aryl-tethered alkynes to vinyl-tethered alkynes involves several serious challenges . Given the importance of cyanoalkylsulfonyl moieties and our ongoing interest in functionalization of an alkene C–H bond, herein, we report a regioselective cascade cyclization of 3-aza-1,5-enynes with sulfur dioxide and cycloketone oxime esters to access cyanoalkylsulfonylated 1,2-dihydropyridines by a copper catalyst (Scheme b).…”

Section: Introductionmentioning

confidence: 99%

Copper Catalyst-Promoted Regioselective Multicomponent Cascade Cyclization of 3-Aza-1,5-enynes with Sulfur Dioxide and Cycloketone Oxime Esters to Access Cyanoalkylsulfonylated 1,2-Dihydropyridines

Ding,

Zhang,

Yang

et al. 2024

J. Org. Chem.

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Radical cascade cyclization via the cracking of alkenyl C−H has emerged as an attractive and remarkable tool for the rapid construction of ring frameworks with endocyclic double bonds. We developed a cascade reaction of 3-aza-1,5-enynes with sulfur dioxide and cycloketone oxime esters to access cyanoalkylsulfonylated 1,2-dihydropyridines, which can be easily converted to pyridine derivatives. This protocol involves radical addition to the C�C bond and 6-endo cyclization and features high regioselectivity and a broad substrate scope.

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Section: Introductionmentioning

confidence: 99%

Copper Catalyst-Promoted Regioselective Multicomponent Cascade Cyclization of 3-Aza-1,5-enynes with Sulfur Dioxide and Cycloketone Oxime Esters to Access Cyanoalkylsulfonylated 1,2-Dihydropyridines

Ding,

Zhang,

Yang

et al. 2024

J. Org. Chem.

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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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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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Photoredox-Catalyzed Synthesis of 3-Sulfonylated Pyrrolin-2-ones via a Regioselective Tandem Sulfonylation Cyclization of 1,5-Dienes

Cited by 5 publications

References 70 publications

Copper Catalyst-Promoted Regioselective Multicomponent Cascade Cyclization of 3-Aza-1,5-enynes with Sulfur Dioxide and Cycloketone Oxime Esters to Access Cyanoalkylsulfonylated 1,2-Dihydropyridines

Copper Catalyst-Promoted Regioselective Multicomponent Cascade Cyclization of 3-Aza-1,5-enynes with Sulfur Dioxide and Cycloketone Oxime Esters to Access Cyanoalkylsulfonylated 1,2-Dihydropyridines

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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