Asymmetric catalytic synthesis of functionalized tetrahydroquinolines in supercritical fluids

Filatova, Evgeniya; Turova, O. V.; Kuchurov, Ilya V.; Kostenko, Alexey A.; Nigmatov, A. G.; Zlotin, Sergei G.

doi:10.1016/j.supflu.2015.11.004

Cited by 27 publications

(13 citation statements)

References 83 publications

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“…Bifunctional tertiary amines were used as organocatalysts and the best results were achieved with cinchona–squaramide C87 . The substrate scope of N ‐tosylated chalcones 161 was also extended, and various tetrahydroquinolines 162 in good yields with high enantioselectivities (up to 96 % ee ) were synthesized (Scheme b) …”

Section: Organocatalysis In Green Solventsmentioning

confidence: 99%

Green Asymmetric Organocatalysis

et al. 2020

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Scheme12. At extile-supported organocatalyst for anhydride opening; MTBE = methyl tert-butyl ether.Scheme13. Organocatalytic aldolreaction conductedb yu sing the continuous-flow technique.Scheme11. PS-immobilized catalyst C32 for the amination of oxindoles 32.Scheme40. Photo-organocatalytic hydroxylation of ketoesters and amides. LED = light-emitting diode.Scheme41. Light-promoted cyclization.Scheme42. Light-promoted alkylation of aldehydes. EWG = electron-withdrawinggroup.Scheme49. Primary-aminec atalyzed light-promoted alkylations of dicarbonyl compounds.Scheme48. Light-promoted organocatalytic Michael additions.

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Section: Organocatalysis In Green Solventsmentioning

confidence: 99%

Green Asymmetric Organocatalysis

et al. 2020

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“…The use of supercritical CO 2 (scCO 2 ) as an alternative green solvent in different reactions is receiving considerable attention due to its numerous advantageous properties . Surprisingly, in contrast to many reports on transition metal catalysis in scCO 2 , studies dealing with organocatalysis in this environmentally friendly medium are extremely rare . This is probably due to low solubility of polar organocatalysts in nonpolar scCO 2 .…”

Section: Introductionmentioning

confidence: 99%

Imidazolium Based Fluorous N‐Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification

et al. 2020

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A series of new highly fluorophilic ionic liquids (f > 110) was synthetized from 3‐iodopropyltris(3,3,4,4,5,5,6,6,7,7,8,8,8‐tridecafluorooctyl)silane and N‐alkyl imidazoles, followed by anion exchange. N‐heterocyclic carbenes generated in situ from obtained imidazolium salts were employed to catalyze redox esterification (umpolung) of cinnamaldehyde with alcohols. The most effective N‐methyl derivative with iodide as a counter anion was studied in detail with respect to the optimization of reaction conditions, substrate scope and recyclability. Recovery of the precatalyst was achieved using either fluorous extraction or performing the reaction in suitable fluorous biphase system with direct recycling of the fluorinated precatalyst phase. For both tested options, the catalytic activity did not significantly decrease within 5 subsequent cycles. The redox esterification was shown to proceed also in supercritical carbon dioxide (scCO2) as an alternative solvent where the activity of the fluorinated catalyst was also superior to the nonfluorinated model, while retaining the benefit of easy recycling.

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“…[26][27][28][29] Supercritical CO 2 (scCO 2 )h as been often used in chemistry and chemical engineering as a green extracting agent of useful substances from plant and animal raw materials, [30] as an inexpensive and efficient eluent Ag lobal increasei ne nvironmental pollutiond emands the development of new "cleaner" chemical processes. Homogeneous [32] andh eterogeneous [33] catalytic or biocatalytic (enzymatic) reactions, [34][35][36] green polymerization processes, [15,16,37] and some other chemical reactions [38][39][40] were performed efficientlyi ns ub-and supercritical CO 2 . As ar esult of the favorable combinationo ft heir unique properties, ionicl iquids (ILs), dense gases, and supercritical fluids (SCFs) have gained considerable attention as suitable green chemistry media for the preparation and modification of important chemical compounds and materials.…”

Section: Introductionmentioning

confidence: 99%

“…for chromatography, [31] and as ac onvenient medium for the environmentally friendly preparationo fc hemical compounds and materials. Homogeneous [32] andh eterogeneous [33] catalytic or biocatalytic (enzymatic) reactions, [34][35][36] green polymerization processes, [15,16,37] and some other chemical reactions [38][39][40] were performed efficientlyi ns ub-and supercritical CO 2 . The global concern with regard to environmental safety in differenti ndustrial areas also affected the production of highenergy materials (HEMs).…”

Section: Introductionmentioning

confidence: 99%

Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

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A global increase in environmental pollution demands the development of new "cleaner" chemical processes. Among urgent improvements, the replacement of traditional hydrocarbon-derived toxic organic solvents with neoteric solvents less harmful for the environment is one of the most vital issues. As a result of the favorable combination of their unique properties, ionic liquids (ILs), dense gases, and supercritical fluids (SCFs) have gained considerable attention as suitable green chemistry media for the preparation and modification of important chemical compounds and materials. In particular, they have a significant potential in a specific and very important area of research associated with the manufacture and processing of high-energy materials (HEMs). These large-scale manufacturing processes, in which hazardous chemicals and extreme conditions are used, produce a huge amount of hard-to-dispose-of waste. Furthermore, they are risky to staff, and any improvements that would reduce the fire and explosion risks of the corresponding processes are highly desirable. In this Review, useful applications of almost nonflammable ILs, dense gases, and SCFs (first of all, CO ) for nitration and other reactions used for manufacturing HEMs are considered. Recent advances in the field of energetic (oxygen-balanced and hypergolic) ILs are summarized. Significant attention is paid to the SCF-based micronization techniques, which improve the energetic performance of HEMs through an efficient control of the morphology and particle size distribution of the HEM fine particles, and to useful applications of SCFs in HEM processing that makes them less hazardous.

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Asymmetric catalytic synthesis of functionalized tetrahydroquinolines in supercritical fluids

Cited by 27 publications

References 83 publications

Green Asymmetric Organocatalysis

Green Asymmetric Organocatalysis

Imidazolium Based Fluorous N‐Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification

Prospective Symbiosis of Green Chemistry and Energetic Materials

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