An ionic liquid mediated Friedel-Crafts addition of arenes to isothiocyanates

2003 ◽  
Vol 81 (10) ◽  
pp. 1057-1060 ◽  
Author(s):  
Prashant U Naik ◽  
Susheel J Nara ◽  
Jitendra R Harjani ◽  
Manikrao M Salunkhe
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
Product Formation ◽  
Progressive Increase ◽  
Lewis Acidity ◽  
Optimal Amount ◽  
Lewis Acid Catalyst

A new protocol is developed for the synthesis of N-substituted thioamides, employing arenes and isothiocyanates in 1-butyl-3-methylimidazolium chloroaluminate ionic liquid, [bmim]Cl·2AlCl3, as a homogenous Lewis acid catalyst and solvent. The effect of Lewis acidity and the stoichiometry of the ionic liquid on the extent of product formation is studied. Studies reveal that a progressive increase in yields was observed with increasing Lewis acidity, and two equivalents of [bmim]Cl·2AlCl3 was the optimal amount for the reaction. A distinct para selectivity for the incoming thioamido group on activated arenes was observed under ambient conditions.Key words: arenes, isothiocyanates, Friedel–Crafts, ionic liquids, thioamides.

Ytterbium(III) triflate catalyzed synthesis of calix[4]pyrroles in ionic liquids

2008 ◽  
Vol 86 (9) ◽  
pp. 899-902 ◽  
Author(s):  
Anil Kumar ◽  
Israr Ahmad ◽  
M Sudershan Rao
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
High Yield ◽  
Ytterbium Triflate ◽  
Lewis Acid Catalyst

Ytterbium(III) triflate has been utilized as a mild Lewis-acid catalyst for the synthesis of various calix[4]pyrroles by the condensation of pyrrole with different ketones in ionic liquids. The calix[4]pyrroles were obtained in high yield under ecofriendly, economical, and noncorrosive conditions, and the catalyst was recovered and recycled.Key words: calix[4]pyrrole, ionic liquid, ytterbium triflate.

Mechanism of Glucose Conversion into 5-Ethoxymethylfurfural in Ethanol with Hydrogen Sulfate Ionic Liquid Additives and a Lewis Acid Catalyst

2018 ◽  
Vol 32 (8) ◽  
pp. 8411-8419 ◽  
Author(s):  
Haixin Guo ◽  
Alif Duereh ◽  
Yuya Hiraga ◽  
Xinhua Qi ◽  
Richard Lee Smith
Keyword(s):  
Ionic Liquid ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
Hydrogen Sulfate ◽  
Lewis Acid Catalyst

Baeyer Condensation in Chloroaluminate Ionic Liquid

2003 ◽  
Vol 2003 (3) ◽  
pp. 168-169 ◽  
Author(s):  
Aniruddha M. Paul ◽  
Amit C. Khandekar ◽  
Bhushan M. Khadilkar
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
Lewis Acid ◽  
Reaction Medium ◽  
Acid Catalyst ◽  
Dual Purpose ◽  
Lewis Acid Catalyst ◽  
Substituted Benzaldehydes

1- n-butylpyridinium chloroaluminate serves the dual purpose of a reaction medium and a Lewis acid catalyst for condensation of substituted benzaldehydes with N, N-dimethylaniline to obtain triarylmethanes (leuco bases) in good yields with significant reduction in reaction time and simplification of the workup process.

scholarly journals PRAVADOLINE SYNTHESIS USING AN IMIDAZOLIUM-BASED IONIC LIQUID AS A GREEN SOLVENT

2011 ◽  
Vol 14 (3) ◽  
pp. 79-86
Author(s):  
Nam Thanh Son Phan ◽  
Ha Vu Le
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Acid Catalyst ◽  
High Yield ◽  
Viet Nam ◽  
Pharmaceutical Chemical ◽  
Green Solvents ◽  
Green Solvent ◽  
1H And 13C Nmr ◽  
Lewis Acid Catalyst

An easily accessible ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]) was synthesized, and characterized using 1H and 13C NMR, and MS. The ionic liquid was demonstrated to be an efficient green solvent for the synthesis of pravadoline, one of non-steroidal drugs. High yield was achieved without the presence of an anhydrous Lewis acid catalyst. The reaction was also successfully carried out using other imidazolium-based ionic liquids, including 1-hexyl-3-methylimidazolium hexafluorophosphate ([HMIM][PF6]), and 1-octyl-3- methylimidazolium hexafluorophosphate ([OMIM][PF6]). To our best knowledge, this is the first report in Viet Nam on the synthesis of a pharmaceutical chemical in ionic liquids as green solvents.

scholarly journals New nano-Fe3O4-supported Lewis acidic ionic liquid as a highly effective and recyclable catalyst for the preparation of benzoxanthenes and pyrroles under solvent-free sonication

RSC Advances ◽  
2018 ◽  
Vol 8 (62) ◽  
pp. 35681-35688 ◽  
Author(s):  
Hai Truong Nguyen ◽  
Ngoc-Phuong Thi Le ◽  
Duy-Khiem Nguyen Chau ◽  
Phuong Hoang Tran
Keyword(s):  
Ionic Liquid ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
Solvent Free ◽  
Acidic Ionic Liquid ◽  
Magnetically Separable Catalyst ◽  
Lewis Acid Catalyst ◽  
Magnetically Separable ◽  
Nano Fe3o4 ◽  
Lewis Acidic Ionic Liquid

A novel magnetically separable catalyst can be used as a green solid Lewis acid catalyst in the synthesis of benzoxanthenes and pyrroles under solvent-free sonication.

Chemoselective hydration of nitriles to amides using hydrated ionic liquid (IL) tetrabutylammonium hydroxide (TBAH) as a green catalyst

RSC Advances ◽  
2015 ◽  
Vol 5 (9) ◽  
pp. 6365-6371 ◽  
Author(s):  
Hojat Veisi ◽  
Behrooz Maleki ◽  
Mona Hamelian ◽  
Samaneh Sedigh Ashrafi
Keyword(s):  
Ionic Liquid ◽  
Base Metal ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
Tetrabutylammonium Hydroxide ◽  
Green Catalyst ◽  
Chemoselective Synthesis ◽  
Lewis Acid Catalyst

A green, chemoselective synthesis of amides, avoiding the use of any base, metal, or Lewis acid catalyst.

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