Bifunctional acid–base ionic liquid for the one-pot synthesis of fine chemicals: Thioethers, 2H-chromenes and 2H-quinoline derivatives

Climent, María J.; Iborra, Sara; Sabater, Marı́a J.; Vidal, Juan D.

doi:10.1016/j.apcata.2014.05.004

Cited by 18 publications

(4 citation statements)

References 64 publications

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“…Very recently, Sabater and co-workers reported another organocatalytic approach to 2 H -chromenes involving the coupling of salicylaldehyde with different electron-deficient alkenes in the presence of an ionic liquid catalyst 343 (Scheme ). Although these particular reactions are not enantioselective, they are nonetheless included here in section for completeness.…”

Section: Enantioselective Organocatalytic 2h-chromene Synthesismentioning

confidence: 99%

Catalytic Synthesis of 2H-Chromenes

et al. 2015

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2H-Chromenes (2H-1-benzopyran derivatives) display a broad spectrum of biological activities. The 2H-chromene substructure is an important structural motif present in a variety of medicines, natural products, and materials showing unique photophysical properties. Hence, the structural importance of the benzopyran moiety has elicited a great deal of interest in the field of organic synthesis and chemical biology to develop new and improved synthesis of these molecular skeletons. This review gives an up-to-date overview of different catalytic methodologies developed for the synthesis of 2H-chromenes and is structured around the three main approaches applied in catalytic 2H-chromene synthesis: (I) catalysis with (transition) metals, (II) metal-free Brønsted and Lewis acid/base catalysis, which includes examples of nonenantioselective organocatalysis, and (III) enantioselective organo-catalysis. The section in which the metal-catalyzed reactions are discussed describes different ring-closing strategies based on (transition) metal catalysis, including a few enantioselective approaches. For most of these reactions, plausible mechanisms are delineated. Moreover, synthesis of some natural products and medicinally important drugs are included. Specific advantages and disadvantages of the several synthetic methodologies are discussed. The review focuses on catalytic 2H-chromene synthesis. However, for a complete overview, synthetic routes involving some stoichiometric steps and reactions producing ring-scaffolds that are closely related to 2H-chromenes are also included.

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Section: Enantioselective Organocatalytic 2h-chromene Synthesismentioning

confidence: 99%

Catalytic Synthesis of 2H-Chromenes

et al. 2015

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“…In the past several years, considerable effort has been made to build chiral chroman derivatives with multichiral centers via asymmetric domino reactions 3 catalyzed by aminocatalysts, 4 thiourea organocatalysts 5 squaramide organocatalysts, 6 and other organocatalysts. 7 Among these approaches, the addition to nitroolefins is a simple but highly efficient route to obtain chiral chromans containing nitro-group, and the nitro group can often lead to changes in chemical and physical properties. 4 d – h ,4 j ,5 b – d In 2013, Zhu et al reported the organocatalytic oxa-Michael-Michael cascade strategy for the construction of spiro [chroman/tetrahydroquinoline-3,3′-oxindole] scaffolds from 2-hydroxynitrostyrenes and N-Boc-protected methyleneindolinones using a squaramide-cinchona bifunctional catalyst.…”

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confidence: 99%

Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction

et al. 2018

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“…Based on the above experimental findings and relative cooperative catalysis reports, [19,23,39] a possible reaction pathway for the reaction of 1 a with 2 a over [SO 3 HPrMIm][OTf] is proposed as illustrated in Scheme 5. Initially, [SO 3 HPrMIm][OTf] activates 2 a by two hydrogen bonds via transient state TS1, meanwhile it catalyzes 1 a dehydration to form dibenzyl ether intermediate 5 a stabilized by the IL.…”

Section: Resultsmentioning

confidence: 99%

A Green Route to Benzyl Phenyl Sulfide from Thioanisole and Benzyl Alcohol over Dual Functional Ionic Liquids

Wang

Qian

et al. 2022

Chemistry An Asian Journal

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Benzyl phenyl sulfide is a kind of important chemicals with wide usage, which is mainly prepared through a nucleophilic reaction of thiophenol with benzyl chlorides or benzyl alcohols, suffering from inherent drawbacks, such as low efficiency, requirements for equivalent acid or base catalysts and formation of harmful byproducts and waste. Herein, we report a green route to access various benzyl phenyl sulfide derivatives in good to excellent yields under mild conditions via the reaction of thioanisoles with benzyl alcohols over ionic liquid 1-propylsulfonate-3-meth-ylimidazolium trifluoromethanesulfonate ([SO 3 HPrMIm][OTf]). Mechanism investigation indicates that the synergic effect of cation and anion of [SO 3 HPrMIm][OTf] activates thioanisoles and benzyl alcohols via hydrogen bonding, thus catalyzes the dehydration of benzyl alcohol to dibenzyl ether and the subsequent metathesis reaction between dibenzyl ether and benzyl phenyl sulfide, finally generating benzyl phenyl sulfide derivatives. This is a simple, highly efficient, and green approach to produce benzyl phenyl sulfide derivatives, which has promising application potentials.

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Bifunctional acid–base ionic liquid for the one-pot synthesis of fine chemicals: Thioethers, 2H-chromenes and 2H-quinoline derivatives

Cited by 18 publications

References 64 publications

Catalytic Synthesis of 2H-Chromenes

Catalytic Synthesis of 2H-Chromenes

Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction

A Green Route to Benzyl Phenyl Sulfide from Thioanisole and Benzyl Alcohol over Dual Functional Ionic Liquids

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