Metal-free 2-isocyanobiaryl-based cyclization reactions: phenanthridine framework synthesis

Doraghi, Fatemeh; Amini, Ali; Ghanbarlou, Mehdi; Larijani, Bagher; Mahdavi, Mohammad

doi:10.1007/s11030-023-10743-2

Mol Divers

2023

DOI: 10.1007/s11030-023-10743-2

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Metal-free 2-isocyanobiaryl-based cyclization reactions: phenanthridine framework synthesis

Fatemeh Doraghi,

Ali Amini,

Mehdi Ghanbarlou

et al.

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2024

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Cited by 3 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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Trifunctionalization of CC bonds in vinyl azides to access densely functionalized phenanthridines enabled by the NCS/AgNO₂ system

Ren,

Zhu,

Liu

2024

Org. Biomol. Chem.

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Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

Ogawa,

Yamamoto

2024

Beilstein J. Org. Chem.

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Isocyanide is a promising synthetic reagent not only as a one-carbon homologation reagent but also as a nitrogen source for nitrogen-containing molecules. Because of their isoelectronic structure with carbon monoxide, isocyanides also react with nucleophiles, electrophiles, carbon radicals, and transition metal reagents, and are widely used in organic synthesis. On the other hand, the use of isocyanides in reactions with heteroatom radicals is limited. However, the reaction of isocyanides with heteroatom radicals is a promising synthetic tool for the construction of nitrogen-containing organic molecules modified with a variety of heteroatoms. In this Perspective, we review the addition and cyclization reactions of heteroatom radicals with isocyanides and discuss the synthetic prospects of the reaction of isocyanides with heteroatom radicals.

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Metal-free 2-isocyanobiaryl-based cyclization reactions: phenanthridine framework synthesis

Cited by 3 publications

References 92 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

Trifunctionalization of CC bonds in vinyl azides to access densely functionalized phenanthridines enabled by the NCS/AgNO₂ system

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

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Metal-free 2-isocyanobiaryl-based cyclization reactions: phenanthridine framework synthesis

Cited by 3 publications

References 92 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

Trifunctionalization of CC bonds in vinyl azides to access densely functionalized phenanthridines enabled by the NCS/AgNO2 system

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

Contact Info

Product

Resources

About

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

Trifunctionalization of CC bonds in vinyl azides to access densely functionalized phenanthridines enabled by the NCS/AgNO₂ system