Highly Selective Aromatic Alkylation of Phenol and Anisole by Using Recyclable Brønsted Acidic Ionic Liquid Systems

Titze-Frech, Karin; Ignatíev, Nikolai; Uerdingen, Marc; Schulz, Peter S.; Wasserscheid, Peter

doi:10.1002/ejoc.201300579

Cited by 18 publications

(6 citation statements)

References 42 publications

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“…63 In accordance with this, only specially designed BAILs have been reported to catalyze this reaction; otherwise, the Friedel−Crafts alkylation of phenol does not work in any conventional IL. 64 These results strongly support a direct connection between alkane microdomains and strong Lewis acidity in the IL. Kinetic experiments (Figure S13) show that the alkylation reaction follows the rate equation…”

Section: Catalytic Alkylation Of Phenolsupporting

confidence: 52%

Acid Catalysis with Alkane/Water Microdroplets in Ionic Liquids

Greco

Lloret

Rivero‐Crespo

et al. 2021

JACS Au

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Ionic liquids are composed of an organic cation and a highly delocalized perfluorinated anion, which remain tight to each other and neutral across the extended liquid framework. Here we show that n -alkanes in millimolar amounts enable a sufficient ion charge separation to release the innate acidity of the ionic liquid and catalyze the industrially relevant alkylation of phenol, after generating homogeneous, self-stabilized, and surfactant-free microdroplets (1–5 μm). This extremely mild and simple protocol circumvents any external additive or potential ionic liquid degradation and can be extended to water, which spontaneously generates microdroplets ( ca . 3 μm) and catalyzes Brönsted rather than Lewis acid reactions. These results open new avenues not only in the use of ionic liquids as acid catalysts/solvents but also in the preparation of surfactant-free, well-defined ionic liquid microemulsions.

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Section: Catalytic Alkylation Of Phenolsupporting

confidence: 52%

Acid Catalysis with Alkane/Water Microdroplets in Ionic Liquids

Greco

Lloret

Rivero‐Crespo

et al. 2021

JACS Au

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“…Titze-Frech and coworkers developed an efficient and selective methodology for the alkylation of phenol and anisole using Bronsted acidic triflate ionic liquid [MIMBS] [OTf] as catalyst in a biphasic reaction medium [106]. This protocol is advantageous over the existing ones as it negates the need for the neutralization of excess acid formed as a by-product.…”

Section: As Acid Catalystsmentioning

confidence: 99%

Ionic Liquids: Synthesis and Applications in Catalysis

Rajni

2014

Advances in Chemistry

211

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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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“…Different from the above process, when the solutes exhibiting immiscibility with water are mixed with ionic liquids, it is preferable to use organic solvents to extract the solutes from the ionic liquids. A range of organic solvents, including ethyl acetate, 112 diethyl ether, 78,113–116 toluene, 60 hexane, 113,117 cyclohexane 118 and the mixture of ethanol and acetone, 77 etc. , have been applied to extract hydrophobic solutes from ILs.…”

Section: Methods For Recovery and Purification Of Ionic Liquids From ...mentioning

confidence: 99%