Deep Eutectic Solvents and Multicomponent Reactions: Two Convergent Items to Green Chemistry Strategies

Calvo‐Flores, Francisco G.; Mingorance-Sánchez, Cristina

doi:10.1002/open.202100137

Cited by 53 publications

(29 citation statements)

References 162 publications

(185 reference statements)

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“…Furthermore, taking advantage of some peculiar properties like high viscosity, conductivity, and polarity, as well as high solubility in water, which usually simplify the isolation of the final products, DESs have been successfully employed as alternatives to VOCs in many organic and organometallic transformations. − For example, the employment of polar organometallic reagents like alkyl- and aryllithium species , in DESs has been successfully proven under mild conditions and very short reaction times. A very important class of transformations that were positively affected by the use of DESs consist of cross-coupling reactions, as reported for Suzuki–Miyaura, − Sonogashira, ,, Hiyama, , Negishi, Stille–Migita, and Ullmann-type − reactions, which have been extensively investigated in recent years.…”

Section: Introductionmentioning

confidence: 99%

Sustainable Pd-Catalyzed Direct Arylation of Thienyl Derivatives with (Hetero)aromatic Bromides under Air in Deep Eutectic Solvents

D’Amico

Papucci

Franchi

et al. 2022

ACS Sustainable Chem. Eng.

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An optimized protocol for the Pd-catalyzed direct arylation of 3,4-ethylenedioxythiophene (EDOT) and other substituted thiophenes with (hetero)aromatic bromides in a deep eutectic solvent made of a mixture of choline chloride/glycerol (1:2) is presented. The coupling reactions have been successfully run under air, in nonanhydrous conditions, using PdCl 2 as a palladium source, with a catalyst loading as low as 1 mol %. The adjustment of each reaction component allowed finding robust conditions for the introduction of both electron-poor and electronrich (hetero)aryl bromides with moderate-to-high yields. The sustainability of the protocol was established through calculations of green metrics, such as Eco-scale and E-factor, and compared with the literature, when possible. Remarkably, such procedure can be successfully applied for the simple preparation of conjugated organic compounds with potential applications in optoelectronics, as we have shown, by obtaining two molecules previously reported as a hole transport material for perovskite solar cells and the final intermediate of a photosensitizer for dye-sensitized solar cells.

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Section: Introductionmentioning

confidence: 99%

Sustainable Pd-Catalyzed Direct Arylation of Thienyl Derivatives with (Hetero)aromatic Bromides under Air in Deep Eutectic Solvents

D’Amico

Papucci

Franchi

et al. 2022

ACS Sustainable Chem. Eng.

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“…These features, inherent to the studied solvents, merge two essential tools in green chemistry: MCRs and green solvents. [44] Some Kamlet-Taft parameters were determined for the tested oils, [43] allowing for quantitative analysis of solvent effects and thus permitting a rational investigation of other MCRs. Theoretical determination of solvent parameters may also be an alternative.…”

Section: Discussionmentioning

confidence: 99%

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

2022

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In the current Perspective article, we critically review and discuss the importance of solvent effects on multicomponent reactions, likely the most neglected aspect in this research field. Although solvent-free reactions may be desirable sometimes, most multicomponent reactions still require a solvent to properly promote them. This requirement makes the knowledge of all drawbacks and advantages of each solvent a central issue when trying to optimize multicomponent reactions. Yet, only a few studies with actual evidence of solvent effects on these key reactions have been published. For the quantitative effects of solvents, studies are even scarcer. In this Perspective, we argue that greater efforts should be directed to such fundamental studies.

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Section: Table 1 Optimization Study For 2-phenylbenzoth...mentioning

confidence: 99%

“…It has good thermal stability, low saturated vapor pressure, non-flammability and explosiveness, recyclability, conforms to the characteristics of green solvents, and is a superior substitute for traditional solvents. [32][33][34][35][36] Furthermore, deep eutectic solvents are low-cost, stable, and simple to handle. [37][38][39] Therefore, this study focused on the use of deep eutectic solvents during the reaction of -phenylglyoxylic acids with ortho-functionalized anilines (o-SH, o-OH, and o-NH) to synthesize 2-arylbenzothiazole, 3-aryl-2H-benzo-[b] [1,4]oxazin-2-one, and 3-arylquinoxalin-2(1H)-one derivatives in good yields.…”

mentioning

confidence: 99%

Reactions of α-Phenylglyoxylic Acids with ortho-Functionalized Anilines in Deep Eutectic Solvents: Selective Syntheses of 3-Aryl-2H-benzo[b][1,4]oxazin-2-ones, 2-Arylbenzothiazoles, and 3-Arylquinoxalin-2(1H)-ones

Jiang¹,

Yang²,

Li³

et al. 2022

Synthesis

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α-Phenylglyoxylic acid is a novel cyclization reagent. In this study, three cyclization products were synthesized by the reaction of α-phenylglyoxylic acids with ortho-functionalized anilines in deep eutectic solvents. The five-membered ring products synthesized using 2-arylbenzothiazole displayed the highest yield of 88 %, obtained by the reaction between 0.30 mmol of o-aminothiophenol and 0.30 mmol of α-phenylglyoxylic acid in choline chloride (ChCl)/D(–)-tartaric acid deep eutectic solvent at 60 °C for 0.5 h. The six-membered ring products synthesized using 3-aryl-2H-benzo[b][1,4]oxazin-2-one derivatives in ChCl/urea deep eutectic solvent displayed a yield of 99 %, obtained by the reaction between 0.30 mmol of an o-aminophenol and 0.60 mmol of an α-phenylglyoxylic acid at 80 °C for 2.0 h. In the reaction between 0.30 mmol of o-phenylenediamine and 0.45 mmol of an α-phenylglyoxylic acid in ChCl/anhydrous tin(II) chloride deep eutectic solvent at 70 °C for 1.5 h, the six-membered ring products, 3-arylquinoxalin-2(1H)-one derivatives, were synthesized, with a highest yield of 96 %. This cyclization reaction occurred without the addition of other catalysts, and the title compounds were obtained with good yields under mild conditions.

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Deep Eutectic Solvents and Multicomponent Reactions: Two Convergent Items to Green Chemistry Strategies

Cited by 53 publications

References 162 publications

Sustainable Pd-Catalyzed Direct Arylation of Thienyl Derivatives with (Hetero)aromatic Bromides under Air in Deep Eutectic Solvents

Sustainable Pd-Catalyzed Direct Arylation of Thienyl Derivatives with (Hetero)aromatic Bromides under Air in Deep Eutectic Solvents

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

Reactions of α-Phenylglyoxylic Acids with ortho-Functionalized Anilines in Deep Eutectic Solvents: Selective Syntheses of 3-Aryl-2H-benzo[b][1,4]oxazin-2-ones, 2-Arylbenzothiazoles, and 3-Arylquinoxalin-2(1H)-ones

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