Redox-Neutral Cyclization of 2-Isocyanobiaryls through Photoredox/PPh<sub>3</sub> Dual Catalysis

Wu, Xiaoting; Chen, Pu; Gan, Mengran; Ji, Xiaochen; Deng, Guo-Jun; Huang, Huawen

doi:10.1021/acs.orglett.3c03744

Org. Lett.

2023

DOI: 10.1021/acs.orglett.3c03744

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Redox-Neutral Cyclization of 2-Isocyanobiaryls through Photoredox/PPh₃ Dual Catalysis

Xiaoting Wu,

Pu Chen,

Mengran Gan

et al.

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2024

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Cited by 8 publications

References 56 publications

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Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh₃ Catalysis

Sui,

Liu,

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryA visible‐light‐induced decarboxylative radical cascade cyclization reaction between N‐(2‐cyanoaryl)‐acrylamides and alkyl N‐(acyloxy)phthalimide (NHPI esters) for the construction of phenanthridine derivatives has been developed. This approach utilizes lithium iodide (LiI) and triphenylphosphine (PPh3) as the redox catalysts and the alkyl radical is produced through the photoactivation of the electron donor‐acceptor (EDA) complex. A series of primary, secondary, and tertiary alkyl‐substituted phenanthridines are prepared in up to 82% yield without transition‐metal catalysts, chemical oxidants, or metal‐/organic dye‐based photocatalysts.

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Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh₃ Catalysis

Sui,

Liu,

et al. 2024

Chin. J. Chem.

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Visible Light‐Induced Radical Tandem Cyclization of o‐Isocyanodiaryl Amines with Arylthiodifluoroalkyl 2‐Pyridyl Sulfones or Difluormethyl‐ Bromides

Liang,

Ai,

Yang

et al. 2024

Eur J Org Chem

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A visible‐light‐induced photoredox‐catalyzed radical tandem cyclization of o‐isocyanodiaryl amines with arylthiodifluoroalkyl 2‐pyridyl sulfones or difluormethyl bromides has been realized for the first time. The reaction works with a broad range of substrates and provides a simple and efficient method for the synthesis of 11‐difluoromethyl‐substituted dibenzodiazepines from easily available starting materials in very mild conditions.

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Accessing 3,4-Dihydroquinolinone from N-Arylacrylamides via Tetralone-Mediated Energy Transfer and 1,3-Hydrogen Shift

Tan,

Zhao,

Deng

et al. 2024

Org. Lett.

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Herein, we introduce a tetralone-mediated photocyclization method of N-arylacrylamides. The protocol proceeds smoothly to deliver a diverse set of 3,4-dihydroquinolinones in moderate to good yields with excellent functional group compatibility and readily allows for late-stage modifications of a number of complex drug molecules. Mechanistic studies reveal that the present systems with ultraviolet light irradiation enable the cyclization via energy transfer and exclusive 1,3-hydrogen shift.

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Redox-Neutral Cyclization of 2-Isocyanobiaryls through Photoredox/PPh₃ Dual Catalysis

Cited by 8 publications

References 56 publications

Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh₃ Catalysis

Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh₃ Catalysis

Visible Light‐Induced Radical Tandem Cyclization of o‐Isocyanodiaryl Amines with Arylthiodifluoroalkyl 2‐Pyridyl Sulfones or Difluormethyl‐ Bromides

Accessing 3,4-Dihydroquinolinone from N-Arylacrylamides via Tetralone-Mediated Energy Transfer and 1,3-Hydrogen Shift

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Redox-Neutral Cyclization of 2-Isocyanobiaryls through Photoredox/PPh3 Dual Catalysis

Cited by 8 publications

References 56 publications

Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh3 Catalysis

Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh3 Catalysis

Visible Light‐Induced Radical Tandem Cyclization of o‐Isocyanodiaryl Amines with Arylthiodifluoroalkyl 2‐Pyridyl Sulfones or Difluormethyl‐ Bromides

Accessing 3,4-Dihydroquinolinone from N-Arylacrylamides via Tetralone-Mediated Energy Transfer and 1,3-Hydrogen Shift

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Product

Resources

About

Redox-Neutral Cyclization of 2-Isocyanobiaryls through Photoredox/PPh₃ Dual Catalysis

Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh₃ Catalysis

Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh₃ Catalysis