Choline Chloride as Catalyst towards the Attractive Yonemitsu Reaction of Benzaldehyde, Indole, and Malononitrile

Yang, Zhou; Liu, Lanye; Zhao, Yihe; Hong, Yuanlin; Ruan, Hongli; Lu, Chunmeng

doi:10.6023/cjoc201803007

Chin. J. Org. Chem.

2018

DOI: 10.6023/cjoc201803007

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Choline Chloride as Catalyst towards the Attractive Yonemitsu Reaction of Benzaldehyde, Indole, and Malononitrile

Zhou Yang¹,

Lanye Liu²,

Yihe Zhao³

et al.

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Synthesis of 3-Substituted Indoles by Yonemitsu Three-Component Reactions Accelerated in Microdroplet/Thin Film

Wu,

Li,

Sun

et al. 2024

J. Org. Chem.

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3-Substituted indoles are an important framework of many drugs, agricultural chemicals, functional materials, and bioactive compounds. Malononitrile-based three-component Yonemitsu reactions are attractive choices for the synthesis of 3substituted indole derivatives but suffered from long reaction time and harsh conditions (e.g., elevated temperature and special catalysts/solvents) in conventional conversions. In this study, we developed a metal-free, efficient, mild, and wide microdroplet/thinfilm method to construct 18 3-substituted indoles from various substituted aromatic aldehydes and indoles with good reaction yields (42−69%) and fantastic reaction acceleration (1.32 × 10 3 rate acceleration factor relative to the bulk reaction). By spraying 0.8 mol L −1 reactants at 300 μL min −1 , the rate of the microdroplet/thin film product was scaled up to 1.72 g h −1 . Overall, the microdroplet/thin-film method offered several advantages including high efficiency, mild conditions, wide scope, and gram-scale ability, making it attractive for synthesizing 3-substituted indoles under the requirements of sustainable chemistry.

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Synthesis of 3-Substituted Indoles by Yonemitsu Three-Component Reactions Accelerated in Microdroplet/Thin Film

Wu,

Li,

Sun

et al. 2024

J. Org. Chem.

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A Facile and Efficient Synthesis of Indole Derivatives in Aqueous Media Catalyzed by [DMAP-SO₃H]Cl and [DMAP-H]HSO₄

Omidi

Mobinikhaledi

Ahadi

2023

Organic Preparations and Procedures International

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Choline Chloride as Catalyst towards the Attractive Yonemitsu Reaction of Benzaldehyde, Indole, and Malononitrile

Cited by 2 publications

References 0 publications

Synthesis of 3-Substituted Indoles by Yonemitsu Three-Component Reactions Accelerated in Microdroplet/Thin Film

Synthesis of 3-Substituted Indoles by Yonemitsu Three-Component Reactions Accelerated in Microdroplet/Thin Film

A Facile and Efficient Synthesis of Indole Derivatives in Aqueous Media Catalyzed by [DMAP-SO₃H]Cl and [DMAP-H]HSO₄

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Choline Chloride as Catalyst towards the Attractive Yonemitsu Reaction of Benzaldehyde, Indole, and Malononitrile

Cited by 2 publications

References 0 publications

Synthesis of 3-Substituted Indoles by Yonemitsu Three-Component Reactions Accelerated in Microdroplet/Thin Film

Synthesis of 3-Substituted Indoles by Yonemitsu Three-Component Reactions Accelerated in Microdroplet/Thin Film

A Facile and Efficient Synthesis of Indole Derivatives in Aqueous Media Catalyzed by [DMAP-SO3H]Cl and [DMAP-H]HSO4

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A Facile and Efficient Synthesis of Indole Derivatives in Aqueous Media Catalyzed by [DMAP-SO₃H]Cl and [DMAP-H]HSO₄