2010
DOI: 10.1002/ejoc.201000456
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Amberlyst‐15 in Ionic Liquid: An Efficient and Recyclable Reagent for Nucleophilic Substitution of Alcohols and Hydroamination of Alkenes

Abstract: The nucleophilic substitution reaction of secondary alcohols and hydroamination of alkenes with amides, sulfonamides, carbamates, and amines using Amberlyst-15 immobilized in [Bmim] [BF 4 ] (1-butyl-3-methylimidazolium tetrafluoroborate) ionic liquid as an efficient recyclable reagent is described. The solvent effect is prominent in the reaction, and

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Cited by 40 publications
(16 citation statements)
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“…It is easy to use, readily removed from the reaction system, and regenerated quickly. It has been reported that Amberlyst-15 could catalyze the nucleophilic substitution of allylic alcohols [29]. Thus, Amberlyst-15 was tried first.…”
Section: Resultsmentioning
confidence: 99%
“…It is easy to use, readily removed from the reaction system, and regenerated quickly. It has been reported that Amberlyst-15 could catalyze the nucleophilic substitution of allylic alcohols [29]. Thus, Amberlyst-15 was tried first.…”
Section: Resultsmentioning
confidence: 99%
“…73 For simplifying workup procedures, Bhanage et al claimed the use of Amberlyst-15 in the ionic liquid [Bmim][BF 4 ] as an efficient recyclable acidic catalyst for hydroamination of alkenes with several nitrogen nucleophiles. 74 All these experiments are a clear demonstration that acid catalysis for these transformations is definitely possible and should be considered when exploring many metal-catalysed systems.…”
Section: Brønsted Acid Catalystsmentioning
confidence: 98%
“…established Markovnikov hydroamination of styrene and its derivatives with amides over metal free ionic liquid grafted on amberlyst‐15, a sulfonic acid group comprising copolymer of styrene and divinylbenzene. However, in this case a side reaction has been noticed along with the desired Markovnikov hydroaminated product, where the phenyl ethyl carbocation on subsequent reaction with styrene and elimination of proton generated the alkene [41] . Grafting of strong acids on solid supports is another protocol which not only reduce the use of corrosive mineral acid but also offers implantation of Bronsted acidic sites on the solid supports.…”
Section: Thermodynamic and Kinetic Aspectsmentioning
confidence: 99%