Brønsted acid ionic liquid catalyzed facile synthesis of 3-vinylindoles through direct C3 alkenylation of indoles with simple ketones

Taheri, Amir; Liu, Changhui; Lai, Bingbing; Cheng, Cheng; Pan, Xun; Gu, Yanlong

doi:10.1039/c4gc00840e

Cited by 62 publications

(28 citation statements)

References 82 publications

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“…A green solvent-free, metal-free, mild, and efficient protocol for the synthesis of 3-vinyl indoles starting from indoles and ketones has been developed using a sulfonyl containing ionic liquid as a recyclable catalyst [104]. The simultaneous presence of sulfonyl and sulphonic acid groups in the same ionic liquid leads to an augmented catalytic activity.…”

Section: As Acid Catalystsmentioning

confidence: 99%

Ionic Liquids: Synthesis and Applications in Catalysis

Rajni

2014

Advances in Chemistry

217

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Ionic liquids have emerged as an environmentally friendly alternative to the volatile organic solvents. Being designer solvents, they can be modulated to suit the reaction conditions, therefore earning the name "task specific ionic liquids. " Though primarily used as solvents, they are now finding applications in various fields like catalysis, electrochemistry, spectroscopy, and material science to mention a few. The present review is aimed at exploring the applications of ionic liquids in catalysis as acid, base, and organocatalysts and as soluble supports for catalysts.

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Section: As Acid Catalystsmentioning

confidence: 99%

Ionic Liquids: Synthesis and Applications in Catalysis

Rajni

2014

Advances in Chemistry

217

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“…The lower reactivity of ketones toward the condensation reaction with indoles necessitates harsher reaction conditions or the utilization of more efficient catalysts. In this context, an ionic liquid Brønsted acid embedding the sulfonic group has been revealed as the most effective catalyst in promoting the reaction of indoles with a large array of ketones (Scheme ) . The process is carried out under solvent‐free condition by simply heating the mixture of reactants in equimolar amount.…”

Section: Addition–elimination Of Indoles To Carbonyl Derivativesmentioning

confidence: 99%

“…In this context,a n ionic liquid Brønsted acid embedding the sulfonic group has been revealed ast he most effectivec atalyst in promoting the reaction of indoles with al arge array of ketones (Scheme 89). [179] The processi sc arried out under solvent-free condition by simply heating the mixture of reactants in equimolar amount. The yields of the obtained products are usually very good even when substituted cycloalkanones are used as substrates.…”

Section: C-3 Alkenylationsmentioning

confidence: 99%

Regioselective Direct C‐Alkenylation of Indoles

Petrini

2017

Chemistry A European J

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The direct introduction of alkenyl groups into the indole framework avoiding its preliminary functionalization can be carried out using different synthetic strategies. Transition-metal complexes facilitate the C-H activation of indoles or alkenes allowing an efficient Csp - Csp bond formation. The hydroindolation of alkynes catalyzed by the same metal complexes or various acidic promoters can also be pursued for the alkenylation process. Conjugate addition of electron-poor alkenes and direct condensation of carbonyl derivatives with indoles are also of interest for this purpose. The regiochemical control can be exploited using the intrinsic C-3 reactivity of the indole ring. The introduction of a suitable directing group at the nitrogen atom allows the preparation of C-2 alkenylated derivatives by transition metal catalyzed reactions. This review collects the fundamental contributions in this field reported in literature during the last fifteen years.

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“…1,1‐Dimethoxy‐3‐butanone is a condensation product of acetone and methyl formate under basic conditions, which has been widely used as an intermediate in drug synthesis. Because 1,1‐dimethoxy‐3‐butanone is a variation of a 1,3‐dicarbonyl compound, its reactivity is thus very close to that of a 1,3‐dicarbonyl compound . We therefore will not discuss its reactions herein.…”

Section: Aliphatic Axb3 Smentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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Brønsted acid ionic liquid catalyzed facile synthesis of 3-vinylindoles through direct C3 alkenylation of indoles with simple ketones

Abstract: A direct dehydrative coupling protocol for the synthesis of 3-vinylindoles using easily available indoles and simple ketones as substrates was developed with the aid of a sulfonyl-containing Brønsted acid ionic liquid.

Cited by 62 publications

References 82 publications

Ionic Liquids: Synthesis and Applications in Catalysis

Ionic Liquids: Synthesis and Applications in Catalysis

Regioselective Direct C‐Alkenylation of Indoles

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

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