Brønsted acidic ionic liquid: a simple, efficient and recyclable catalyst for regioselective alkylation of phenols and anti-Markovnikov addition of thiols to alkenes

Qureshi, Ziyauddin S.; Deshmukh, Krishna M.; Dhake, Kishor P.; Bhanage, Bhalchandra M.

doi:10.1039/c1ra00401h

Cited by 32 publications

(19 citation statements)

References 43 publications

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“…In recent years, ionic liquids have attracted much interest for their unique properties such as non-volatility, non-flammability, high chemical and thermal stability. [11][12][13][14][15] [AlCl3] would result in high activity. These kinds of ionic liquid catalysts could not be reused for many times because of their moisture sensitivity.…”

Section: Introductionmentioning

confidence: 99%

Durability enhanced ionic liquid catalyst for Friedel–Crafts reaction between benzene and 1-dodecene: insight into catalyst deactivation

Wan

Zhang

et al. 2015

RSC Adv.

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Friedel-Craft alkylation of benzene with 1-dodecene, which is an important reaction of synthetic detergent, was studied using the catalyst of [bmim][TFSI]/AlCl3 (1-butyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide/AlCl3). These ionic liquid catalysts show biphasic behaviors at specific condition. Active site species and Lewis acidity were determined by NMR and acetonitrile probe FT-IR. NMR spectroscopy investigations indicated that "Coordinated" and "uncoordinated"[TFSI]existed in the ionic liquid catalyst system sumultaneity, while tetrahedral 4-coordinate Al2Cl7was the main active specie for Friedel-Craft alkylation. The complexation [AlClx(TFSI)y]tend to decompose and release 4-coordinated Al2Cl7and [TFSI] -. The phase behaviors study of the ionic liquid [bmim][TFSI]/AlCl3 demonstrated that the upper phase could be used as an efficient heterogeneous catalyst when AlCl3/IL≥1.5. Due to the presence of anion [TFSI]around active sites, especially [TFSI]at "uncoordinated" state, ionic liquid formed a stable and hydrophobic chemical environment, which enhanced catalysts durability. The influence of various reaction conditions including catalyst reusability on the alkylation reaction was studied, and the potential reasons to catalyst deactivation were discussed. The highest 2-LAB selectivity was more than 50% when 1-dodecene conversion was nearly 100%. Comparing with liquid or solid acid catalyst, ionic liquid catalysts have many advantages in perspectives concerning energy and environmental.

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Section: Introductionmentioning

confidence: 99%

Durability enhanced ionic liquid catalyst for Friedel–Crafts reaction between benzene and 1-dodecene: insight into catalyst deactivation

Wan

Zhang

et al. 2015

RSC Adv.

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“…In another instance, Qureshi et al . utilized brønsted acidic ionic liquid as solvent cum catalyst for anti‐Markovnikov addition of thiols 56 to alkenes 57 for the synthesis of thioether 58 in good yield (Scheme ) …”

Section: Synthetic Methods For Anti‐markovnikov Thiol‐ene Reactionmentioning

confidence: 99%

Thiol−Ene Reaction: Synthetic Aspects and Mechanistic Studies of an Anti‐Markovnikov‐Selective Hydrothiolation of Olefins

2018

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In synthetic organic chemistry, the anti-Markovnikov thiolÀ ene click (TEC) reaction has emerged as a powerful and widely used approach to build carbonÀ sulfur (CÀ S) bonds owing to several inherent benefits, including simple synthetic procedures, high atom economy with no side products, and easy purification, which results in the formation of linear thioethers in high yield under mild reaction conditions. These TEC reactions have numerous trapping applications in the field of nanoengineering, polymer science, and in medicinal chemistry for the synthesis of many drugs and bioactive molecules. This present review highlights the diversity of TEC reaction in terms of substrates, catalysts and mechanistic studies towards the generation of highly selective anti-Markovnikov adduct under metal-free, metalcatalyzed, and photo-induced reaction conditions.

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“…Among them, alkyl or alkenyl hetero-sulfides, which with Markovnikov configuration have been used as building blocks for many pharmaceutical products including 6-mercaptopurine, ranitidine, cimetidine, 4 suffer from more challenges in synthesis, because the tendency of addition reaction of thiol to alkenes and alkynes is in favor of anti-Markovnikov products under the traditional catalysts of H-rho-zeolite and benzene-reflux, 5,6 InI, 7 CeCl 3 , 8 silica nano particles, 9 and acidic ionic liquids. 10 Fortunately, the synergistic transition metal co-catalyst with Markovnikov configuration for the construction of heterosulfide bonds conducted a high effective and simple strategy.…”

Section: Introductionmentioning

confidence: 99%

Palladium and copper co-catalyzed Markovnikov hydrothiolation of terminal olefins and alkynes

Ren

Zhou

et al. 2015

Tetrahedron Letters

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Brønsted acidic ionic liquid: a simple, efficient and recyclable catalyst for regioselective alkylation of phenols and anti-Markovnikov addition of thiols to alkenes

Cited by 32 publications

References 43 publications

Durability enhanced ionic liquid catalyst for Friedel–Crafts reaction between benzene and 1-dodecene: insight into catalyst deactivation

Durability enhanced ionic liquid catalyst for Friedel–Crafts reaction between benzene and 1-dodecene: insight into catalyst deactivation

Thiol−Ene Reaction: Synthetic Aspects and Mechanistic Studies of an Anti‐Markovnikov‐Selective Hydrothiolation of Olefins

Palladium and copper co-catalyzed Markovnikov hydrothiolation of terminal olefins and alkynes

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