Synthesis of 2‐Phosphoryl‐3‐Monofluorovinylindoles under Catalyst‐ and Additive‐Free Conditions

An, Di; Sang, Jingjing; Hu, Rui; Chen, Jichao; Li, Feng; Rao, Weidong

doi:10.1002/adsc.202100331

Cited by 7 publications

(1 citation statement)

References 72 publications

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“…Products of reaction of Ph2P(O)H with difluorinated 3-(αhydroxyalkyl)indoles. [206,207] Figure S22. Products of 3C-reaction of indoles with SPOs and carbonyl compounds.…”

Section: Figure S16mentioning

confidence: 99%

Phospha-Mannich reactions of phosphinous acids R ₂ P–OH and their derivatives

Moiseev¹

2023

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…Products of reaction of Ph2P(O)H with difluorinated 3-(αhydroxyalkyl)indoles. [206,207] Figure S22. Products of 3C-reaction of indoles with SPOs and carbonyl compounds.…”

Section: Figure S16mentioning

confidence: 99%

Phospha-Mannich reactions of phosphinous acids R ₂ P–OH and their derivatives

Moiseev¹

2023

Phosphorus, Sulfur, and Silicon and the Related Elements

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Brønsted Acid-Catalyzed Dehydrative Nazarov-type Cyclization of CF₃-Substituted 3-Indolylallyl Alcohols: Divergent Synthesis of 1-Trifluoromethylated Cyclopenta[b]indoles

Teng,

Yu,

Shang

et al. 2024

J. Org. Chem.

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An expedient and efficient synthetic method for the divergent synthesis of 1-trifluoromethylated cyclopenta [b]indoles that relies on Brønsted acid-catalyzed dehydrative Nazarov-type cyclization of CF 3 -substituted 3-indolylallyl alcohols is described. Two classes of 1-trifluoromethylated cyclopenta[b]indoles can be easily accessed simply by changing the NH-protecting group of indoles. With arylsulfonyl protected 3-indolylallyl alcohols as starting materials, the reaction provided the arylsulfonyl protected 1-trifluoromethylated cyclopenta [b]indoles in good to excellent yields, whereas pivaloyl (Piv) protected substrates led to the formation of NH-free 1-trifluoromethylated cyclolopenta[b]indoles with another alkenyl isomer. This protocol features tunable chemoselectivity, operational simplicity, excellent functional group compatibility, and mild metal-free conditions.

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Sc(OTf)₃-Catalyzed C2-Selective Cyanation/Defluorination Cascade of Perfluoroalkylated 3-Indolylmethanols and Application to the Synthesis of 3-Fluoro(perfluoroalkyl)-β-carbolines

Sang

et al. 2021

Org. Lett.

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An unprecedented Sc(OTf)3-catalyzed C2-selective cyanation/defluorination cascade of perfluoroalkylated 3-indolylmethanols with TMSCN is described, which provides a novel and practical strategy for the synthesis of structurally diverse 3-(2-cyano)-indolyl substituted gem-difluoroalkenes and β-fluoro-β-perfluoroalkylalkenes. The reaction features excellent regio- and stereoselectivity and broad substrate scope. Notably, the obtained gem-difluoroalkenes and β-fluoro-β-perfluoroalkylalkenes could be easily transformed into 3-fluoro(perfluoroalkyl)-β-carbolines with excellent efficiency simply by treating them with Grignard reagents or DIBAL-H under mild reaction conditions.

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Synthesis of 2‐Phosphoryl‐3‐Monofluorovinylindoles under Catalyst‐ and Additive‐Free Conditions

Cited by 7 publications

References 72 publications

Phospha-Mannich reactions of phosphinous acids R ₂ P–OH and their derivatives

Phospha-Mannich reactions of phosphinous acids R ₂ P–OH and their derivatives

Brønsted Acid-Catalyzed Dehydrative Nazarov-type Cyclization of CF₃-Substituted 3-Indolylallyl Alcohols: Divergent Synthesis of 1-Trifluoromethylated Cyclopenta[b]indoles

Sc(OTf)₃-Catalyzed C2-Selective Cyanation/Defluorination Cascade of Perfluoroalkylated 3-Indolylmethanols and Application to the Synthesis of 3-Fluoro(perfluoroalkyl)-β-carbolines

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Synthesis of 2‐Phosphoryl‐3‐Monofluorovinylindoles under Catalyst‐ and Additive‐Free Conditions

Cited by 7 publications

References 72 publications

Phospha-Mannich reactions of phosphinous acids R 2 P–OH and their derivatives

Phospha-Mannich reactions of phosphinous acids R 2 P–OH and their derivatives

Brønsted Acid-Catalyzed Dehydrative Nazarov-type Cyclization of CF3-Substituted 3-Indolylallyl Alcohols: Divergent Synthesis of 1-Trifluoromethylated Cyclopenta[b]indoles

Sc(OTf)3-Catalyzed C2-Selective Cyanation/Defluorination Cascade of Perfluoroalkylated 3-Indolylmethanols and Application to the Synthesis of 3-Fluoro(perfluoroalkyl)-β-carbolines

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Phospha-Mannich reactions of phosphinous acids R ₂ P–OH and their derivatives

Phospha-Mannich reactions of phosphinous acids R ₂ P–OH and their derivatives

Brønsted Acid-Catalyzed Dehydrative Nazarov-type Cyclization of CF₃-Substituted 3-Indolylallyl Alcohols: Divergent Synthesis of 1-Trifluoromethylated Cyclopenta[b]indoles

Sc(OTf)₃-Catalyzed C2-Selective Cyanation/Defluorination Cascade of Perfluoroalkylated 3-Indolylmethanols and Application to the Synthesis of 3-Fluoro(perfluoroalkyl)-β-carbolines