Borenium ionic liquids as catalysts for Diels–Alder reaction: tuneable Lewis superacids for catalytic applications

Matuszek, Karolina; Coffie, Sesime; Chrobok, Anna; Swadźba‐Kwaśny, Małgorzata

doi:10.1039/c7cy00106a

Cited by 30 publications

(23 citation statements)

References 17 publications

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“…18 Left Conversions in Diels-Alder cycloaddition of cyclopentadiene to ethyl acrylate, catalyzed by 0.10 mol% of borenium ILs vs. AN values of the catalysts; right tabulated data listing the formula of each IL catalyst, their corresponding ANs and conversions in Diels-Alder reaction. Adapted from [115] off point for which a sudden increase in conversion was noted, which is characteristic of Lewis acid-catalyzed reactions [85]. Using ILs with the higher ANs, full conversions were achieved within 5 min at 0.1 mol% of catalyst loading, which surpassed all Lewis acidic ILs previously studied in this reaction (viz.…”

Section: Applicationsmentioning

confidence: 95%

“…Nevertheless, none of the above-cited standard reactions were adopted as the standard method. In the recent years, Diels-Alder has been gaining increasing popularity as the benchmark reaction of choice [75,[114][115][116][117].…”

Section: Adapted Solid-state Methods: Ft-ir Spectroscopymentioning

confidence: 99%

“…examples in Schemes 3 and 4)-which lends itself to be translated to IL realm. However, despite increasing interest in these strong Lewis acids in main-group and organic community [28,188,189], their uses in ILs are both very recent and very rare [115,190]. Scheme 3 Synthesis of a borenium ionic liquid via chloride abstraction [191]…”

Section: Historical Contextmentioning

confidence: 99%

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Lewis Acidic Ionic Liquids

Brown

Hogg

Swadźba‐Kwaśny

2017

Topics in Current Chemistry Collections

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Until very recently, the term Lewis acidic ionic liquids (ILs) was nearly synonymous with halometallate ILs, with a strong focus on chloroaluminate(III) systems. The first part of this review covers the historical context in which these were developed, speciation of a range of halometallate ionic liquids, attempts to quantify their Lewis acidity, and selected recent applications: in industrial alkylation processes, in supported systems (SILPs/SCILLs) and in inorganic synthesis. In the last decade, interesting alternatives to halometallate ILs have emerged, which can be divided into two subsections: (1) liquid coordination complexes (LCCs), still based on halometallate species, but less expensive and more diverse than halometallate ionic liquids, and (2) ILs with main-group Lewis acidic cations. The two following sections cover these new liquid Lewis acids, also highlighting speciation studies, Lewis acidity measurements, and applications.

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Section: Applicationsmentioning

confidence: 95%

Section: Adapted Solid-state Methods: Ft-ir Spectroscopymentioning

confidence: 99%

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Lewis Acidic Ionic Liquids

Brown

Hogg

Swadźba‐Kwaśny

2017

Topics in Current Chemistry Collections

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“…The LSA ionic liquids were used to catalyze Diels-Alder reactions, with reaction rates correlatingw ith the determined acceptor numbers. [209] Solid-state LSA:S olid-state superacids( Brønsted and Lewis) are highly important for industrial processes and petrochemistry. [2b, 44b, 210] They mostlyc onsist of activated forms of amorphousm etal oxides or metal halides.…”

Section: Lewis Acidic Transition-metal (Tm) Complexesmentioning

confidence: 99%

Lewis Superacids: Classifications, Candidates, and Applications

Greb

2018

Chemistry A European J

263

242

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Lewis acids play a major role in all areas of chemistry. For a long time, toxic, corrosive and oxidizing SbF was considered as the strongest Lewis acid known. Lately, species significantly exceeding the Lewis acidity of SbF have been realized and were termed Lewis superacids (LSA). Prospective new candidates emerge steadily, which not only outperform SbF by their strength, but also in terms of their accessibility and ease of handling. In principle, Lewis superacids allow us to combine the outstanding activity of Brønsted superacids with the excellent selectivity of a common Lewis acid. However, the broad application of Lewis superacids in synthesis is all but popular. The present review deals with strong Lewis acids. First, it critically discusses Lewis acidity scaling methods and suggests an extended definition for Lewis superacidity. It then summarizes the properties and applications of the strongest currently known Lewis acids, indexed by the fluoride ion affinity (FIA). The supporting information contains a comprehensive list of experimentally and theoretically derived FIA data as a guide for the choice of Lewis acidic reagents/catalyst. This contribution shall encourage the search for new Lewis superacids and promote their application in non-specialized laboratories.

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“…• protonic ionic liquids based on aliphatic and aromatic amines and sulfuric acid, 1 • chlorometallate ionic liquids made from dialkylimidazolium cation and chlorometallate anions (metal: Al(III) or Ga(III)), also immobilized on the surface of a mesoporous silica material with a hierarchical pore structure, 2,3 • borenium ionic liquids based on borenium cation and chlorometallate anions (metal: Al(III), Ga(III)), 4 and • liquid coordination complexes based on selected amines and phosphines and GaCl3. 5 Studied catalysts were characterized by spectroscopic methods and their Gutmann Acceptor Numbers (AN) were determined.…”

Section: Results and Disscutionmentioning

confidence: 99%

Ionic liquids – application driven synthesis in green chemistry

Chrobok¹

2019

Chemical Technology and Engineering. Proceedings.2019.№1

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Ionic liquid-based strategies are presented as a generic approach to tailoring catalysts as a replacement of hazardous acids in industrially-relevant reactions, to generate both environmentally and economically sustainable processes. The possibilities of application of new bronsted and Lewis acidic ionic liquids as catalysts, mainly in the synthesis of fine chemicals: lactones, amides, esters, Diels-Alder cycloadducts and alkilobenzenes are presented. Кеуwordsacidic ionic liquids, fine chemicals, green chemistry, oxidation, esterification.

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Borenium ionic liquids as catalysts for Diels–Alder reaction: tuneable Lewis superacids for catalytic applications

Abstract: Ionic liquids with Lewis superacidic borenium cations were used as catalysts in solvent-less Diels–Alder cycloaddition. The extremely high catalytic activity correlated with the Lewis acidity, expressed as the Gutmann acceptor number.

Cited by 30 publications

References 17 publications

Lewis Acidic Ionic Liquids

Lewis Acidic Ionic Liquids

Lewis Superacids: Classifications, Candidates, and Applications

Ionic liquids – application driven synthesis in green chemistry

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