scholarly journals Natural Deep Eutectic Solvents as Sustainable Solvents for Suzuki­–Miyaura Cross-Coupling Reactions Applied to Imidazo-Fused Heterocycles

SynOpen ◽  
2018 ◽  
Vol 02 (04) ◽  
pp. 0306-0311 ◽  
Author(s):  
Pierre-Olivier Delaye ◽  
Mélanie Pénichon ◽  
Leslie Boudesocque-Delaye ◽  
Cécile Enguehard-Gueiffier ◽  
Alain Gueiffier
Keyword(s):  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Cross Coupling ◽  
Deep Eutectic Solvents ◽  
Coupling Reactions ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Fused Heterocycles ◽  
Natural Deep Eutectic Solvents ◽  
Natural Deep Eutectic Solvent

Herein, we present the first Suzuki–Miyaura cross-coupling in a sustainable natural deep eutectic solvent (NaDES) applied to biologically relevant imidazo-fused scaffolds imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine. The choline chloride/glycerol (1:2, mol/mol) NaDES allowed the functionalisation of diverse positions on the heterocycles with various boronic acids, by using 2.5 mol% of readily available Pd(OAc)2. Notably, the catalytic system proceeds without any ligands or additives, without protection from the atmosphere.

scholarly journals Preparation of Readily-to-Use Stilbenoids Extract from Morus alba Callus Using a Natural Deep Eutectic Solvent

Cosmetics ◽  
2021 ◽  
Vol 8 (3) ◽  
pp. 91
Author(s):  
Jukrapun Komaikul ◽  
Supachoke Mangmool ◽  
Waraporn Putalun ◽  
Tharita Kitisripanya
Keyword(s):  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Dry Weight ◽  
Deep Eutectic Solvents ◽  
Morus Alba ◽  
Green Solvent ◽  
Natural Deep Eutectic Solvents ◽  
Significant Difference ◽  
Natural Deep Eutectic Solvent ◽  
Skin Lightening

The consumer and cosmetic industries have recently placed a greater emphasis on ecofriendly solvents for botanical extraction, including natural deep eutectic solvents (NADES). In this study, NADES were prepared for Morus alba callus extraction. The efficiency of extraction from the NADES and methanol was investigated by comparison of the stilbenoids yield and anti-melanogenesis activity. Prior to testing the irritability of a suitable NADES on the reconstructed human epidermis (RhE), the effect of the selected NADES on stilbenoids stability was determined. The results showed that the highest yields of stilbenoids were obtained from choline chloride-glycerol mixtures (Ch1G2) and methanol extracts, with no significant difference in yields (5.06 ± 0.05 and 6.32 ± 0.40 mg/g callus dry weight, respectively). The NADES extracts of M. alba callus showed comparable anti-melanogenesis activity compared to methanol. In term of stability, stilbenoids in Ch1G2 remained stable after six months of storage at 4 °C except resveratrol. Furthermore, Ch1G2 had no irritation effect on RhE. Thus, based on the findings of this study, Ch1G2 is an intriguing green solvent alternative for the extraction of M. alba callus and may be advantageous for the preparation of skin-lightening cosmetics.

A Revised Modular Approach to D8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Victor Bloemendal ◽  
Floris P. J. T. Rutjes ◽  
Thomas J. Boltje ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Modular Approach ◽  
Coupling Reactions ◽  
One Pot ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Chemistry Research

<p>In this manuscript we describe a modular pathway to synthesize biologically relevant (–)-<i>trans</i>-Δ<sup>8</sup>-THC derivatives, which can be used to modulate the pharmacologically important CB<sub>1</sub> and CB<sub>2</sub> receptors. This pathway involves a one-pot Friedel-Crafts alkylation/cyclization protocol, followed by Suzuki-Miyaura cross-coupling reactions and gives rise to a series of new Δ<sup>8</sup>-THC derivatives. In addition, we demonstrate using extensive NMR evidence that similar halide-substituted Friedel-Crafts alkylation/cyclization products in previous articles were wrongly assigned as the para-isomers, which also has consequence for the assignment of the subsequent cross-coupled products and interpretation of their biological activity. </p> <p>Considering the importance of the availability of THC derivatives in medicinal chemistry research and the fact that previously synthesized compounds were wrongly assigned, we feel this research is describing a straightforward pathway into new cannabinoids.</p>

scholarly journals Deep Eutectic Solvent Compatible Metallic Catalysts: Cationic Pyridiniophosphine Ligands in Palladium Catalyzed Cross-Coupling Reactions

ChemCatChem ◽  
2017 ◽  
Vol 9 (7) ◽  
pp. 1269-1275 ◽  
Author(s):  
Xavier Marset ◽  
Abbas Khoshnood ◽  
Lia Sotorríos ◽  
Enrique Gómez-Bengoa ◽  
Diego A. Alonso ◽  
...  
Keyword(s):  
Deep Eutectic Solvent ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Trifluoromethanesulfonyloxy-group-directed regioselective (3 + 2) cycloadditions of benzynes for the synthesis of functionalized benzo-fused heterocycles

2015 ◽  
Vol 13 (2) ◽  
pp. 520-526 ◽  
Author(s):  
Takashi Ikawa ◽  
Hideki Kaneko ◽  
Shigeaki Masuda ◽  
Erika Ishitsubo ◽  
Hiroaki Tokiwa ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Fused Heterocycles

Highly regioselective (3 + 2) cycloadditions of 3- and 4-TfO-benzynes with 1,3-dipoles followed by cross-coupling reactions provided multisubstituted benzo-fused heterocycles.

scholarly journals Natural Deep Eutectic Solvent-Assisted Pectin Extraction from Pomelo Peel Using Sonoreactor: Experimental Optimization Approach

Processes ◽  
2019 ◽  
Vol 7 (7) ◽  
pp. 416 ◽  
Author(s):  
Amal Elgharbawy ◽  
Adeeb Hayyan ◽  
Maan Hayyan ◽  
Mohamed Mirghani ◽  
Hamzah Salleh ◽  
...  
Keyword(s):  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Optimization Approach ◽  
Degree Of Esterification ◽  
Screening Design ◽  
Natural Deep Eutectic Solvents ◽  
Wide Range ◽  
Definitive Screening ◽  
Water Ratio

Background: Natural deep eutectic solvents (NADESs) can be used for extracting a wide range of biomaterials, such as pectin. This study introduces a new generation of natural solvents for pectin extraction which could replace the conventional solvents in the food industry. Methods: In this study, NADESs were used for pectin extraction from pomelo (Citrus grandis (L.) Osbeck) peels using a sonoreactor. Definitive screening design (DSD) was used to screen the influence of time, temperature, solid/liquid ratio, and NADES/water ratio on the pectin yield and degree of esterification (DE). Results: The primary screening revealed that the best choices for the extraction were choline chloride–malonic acid (ChCl-Mal) and choline chloride–glucose–water (ChCl:Glc:W). Both co-solvents yielded 94% pectin and 52% DE after optimization at 80 °C, with 60 min of sonication, pH < 3.0, and a NADES-to-water ratio of 1:4.5 (v/v). Morphological screening showed a smooth and compact surface of the pectin from ChCl-Mal where glucose-based pectin had a rough surface and lower DE. Conclusions: NADESs proved to be promising co-solvents for pectin extraction with a high degree of esterification (>55%).

scholarly journals Natural Deep Eutectic Solvents for the Extraction of Phenyletanes and Phenylpropanoids of Rhodiola rosea L.

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1826 ◽  
Author(s):  
Alexander N. Shikov ◽  
Vera M. Kosman ◽  
Elena V. Flissyuk ◽  
Irina E. Smekhova ◽  
Abdelhameed Elameen ◽  
...  
Keyword(s):  
Particle Size ◽  
Water Content ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Extraction Yield ◽  
Rhodiola Rosea ◽  
Extraction Temperature ◽  
Natural Deep Eutectic Solvents ◽  
Predicted Values ◽  
Natural Deep Eutectic Solvent

The extraction of Rhodiola rosea rhizomes using natural deep eutectic solvent (NADES) consisting of lactic acid, glucose, fructose, and water was investigated. A two-level Plackett–Burman design with five variables, followed by the steepest ascent method, was undertaken to determine the optimal extraction conditions. Among the five parameters tested, particle size, extraction modulus, and water content were found to have the highest impact on the extrability of phenyletanes and phenylpropanoids. The concentration of active compounds was analyzed by HPLC. The predicted results showed that the extraction yield of the total phenyletanes and phenylpropanoids (25.62 mg/g) could be obtained under the following conditions: extraction time of 154 min, extraction temperature of 22 °C, extraction modulus of 40, molar water content of 5:1:11 (L-lactic acid:fructose:water, mol/mol), and a particle size of rhizomes of 0.5–1 mm. These predicted values were further verified by validation experiments in predicted conditions. The experimental yields of salidroside, tyrosol, rosavin, rosin, cinnamyl alcohol and total markers (sum of phenyletanes and phenylpropanoids in mg/g) were 11.90 ± 0.02, 0.36 ± 0.02, 12.23 ± 0.21, 1.41 ± 0.01, 0.20 ± 0.01, and 26.10 ± 0.27 mg/g, respectively, which corresponded well with the predicted values from the models.

scholarly journals Natural Deep Eutectic Solvent as Extraction Media for the Main Phenolic Compounds from Olive Oil Processing Wastes

Antioxidants ◽  
2020 ◽  
Vol 9 (6) ◽  
pp. 513 ◽  
Author(s):  
Sonia Bonacci ◽  
Maria Luisa Di Gioia ◽  
Paola Costanzo ◽  
Loredana Maiuolo ◽  
Sofia Tallarico ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Olive Oil ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Extraction Process ◽  
Oil Processing ◽  
Flight Mass Spectrometry ◽  
Natural Deep Eutectic Solvents ◽  
Processing Wastes ◽  
Natural Deep Eutectic Solvent

In this new century, sustainable development challenges chemical sciences to develop new and clean technological processes. The agri-food industry produces significant quantities of waste, raising significant economic and environmental concerns. Food waste valorization using environmentally friendly procedures is of increasing importance. This study describes the use of several Natural Deep Eutectic Solvents (NADESs) for the microwave-assisted extraction (MAE) of valuable bioactive phenolic compounds from olive oil processing wastes. The extracted samples were characterized by liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry (LC-ESI-QTOF/MS) analysis and the quantification of the phenolic compounds was performed by HPLC analysis. The obtained data were compared with those obtained using water as the solvent in the same extraction conditions. The extraction process is nontoxic, simple and selective and meets most of the criteria to be considered as a sustainable process, with the solvents arising directly from nature.

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