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Organic Reaction in Green Solvents

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Green Chemistry".

Deadline for manuscript submissions: closed (30 June 2016) | Viewed by 47786

Special Issue Editors


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Guest Editor
Laboratorio de Compuestos Organometálicos y Catálisis (Unidad Asociada al CSIC), Departamento de Química Orgánica e Inorgánica (IUQOEM), Facultad de Química, Universidad de Oviedo, E-33071 Oviedo, Spain
Interests: homogeneous catalysis; organometallic chemistry; green chemistry; sustainable solvents; deep eutectic solvents; water
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
Centre for Green Chemical Science, School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland 1000, New Zealand
Interests: sustainable synthesis; chitin valorisation; green chemistry; mechanochemistry; electrochemistry​

Special Issue Information

Dear Colleagues,

Due to both environmental and economic issues, chemistry is driven to reduce waste and re-use materials in order to meet the standards of the 12 Principles of Green Chemistry. These Principles have become a widely accepted set of criteria for the assessment of the Greenness of a given chemical transformation.

In this sense, the choice of a safe, non-toxic, biorenewable, and cheap solvent is a crucial goal in metal-catalyzed organic reactions. Thus, one of the largest areas of consumption of petroleum-based chemicals in a conventional metal-catalyzed organic transformation is the solvent used as a reaction medium (i.e., solvents account for 80-90% of mass utilization in a typical pharmaceutical/fine chemical operational process). On top of this, conventional volatile organic solvents (VOCs), commonly used as reaction media in metal-mediated organic procedures, can cause well-established environmental problems due to their: i) high toxicity; ii) non-biodegradability; iii) accumulation in the atmosphere (low boiling points); and iv) flammability.

To overcome the drawbacks of traditional VOCs, and to still benefit from the solvent effect, remarkable research efforts have been focused on the replacement of traditional organic solvents by Green Solvents.

Dr. Joaquín García Álvarez
Dr. Jonathan Sperry
Guest Editors

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Green Solvents,
  • Water,
  • Bio-derived solvents,
  • Glycerol,
  • scCO2,
  • Deep Eutectic Solvents,
  • Ionic Liquids,
  • perfluorinated solvents

Published Papers (8 papers)

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Editorial

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154 KiB  
Editorial
Special Issue: “Organic Reactions in Green Solvents”
by Jonathan Sperry and Joaquín García-Álvarez
Molecules 2016, 21(11), 1527; https://doi.org/10.3390/molecules21111527 - 15 Nov 2016
Cited by 16 | Viewed by 4761
Abstract
To overcome the well-established drawbacks of conventional organic solvents (toxicity, non-biodegradability, flammability, accumulation in the atmosphere) remarkable research efforts have been recently devoted to the replacement of traditional organic reaction media by the so-called Green Solvents. In this sense, the choice of [...] Read more.
To overcome the well-established drawbacks of conventional organic solvents (toxicity, non-biodegradability, flammability, accumulation in the atmosphere) remarkable research efforts have been recently devoted to the replacement of traditional organic reaction media by the so-called Green Solvents. In this sense, the choice of a safe, non-toxic, biorenewable and cheap reaction media is a crucial goal in organic synthesis. Thus, this Special Issue on “Organic Reactions in Green Solvents” has been aimed to showcase a series of stimulating contributions from international experts within different sub-areas of organic synthesis in Green Solvents (ranging from metal- to organo-catalyzed organic reactions). Full article
(This article belongs to the Special Issue Organic Reaction in Green Solvents)

Research

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985 KiB  
Article
Transformation of Tertiary Benzyl Alcohols into the Vicinal Halo-Substituted Derivatives Using N-Halosuccinimides
by Njomza Ajvazi and Stojan Stavber
Molecules 2016, 21(10), 1325; https://doi.org/10.3390/molecules21101325 - 02 Oct 2016
Cited by 9 | Viewed by 7089
Abstract
The efficiency of direct conversion of tertiary alcohols bearing a β-hydrogen atom to vicinal halohydrins—chlorohydrins and bromohydrins—under green reaction conditions was tested preliminarily on model tertiary benzyl alcohols. Tertiary alcohols were successfully directly halogenated to vicinal halohydrins with N-halosuccinimide in aqueous media. [...] Read more.
The efficiency of direct conversion of tertiary alcohols bearing a β-hydrogen atom to vicinal halohydrins—chlorohydrins and bromohydrins—under green reaction conditions was tested preliminarily on model tertiary benzyl alcohols. Tertiary alcohols were successfully directly halogenated to vicinal halohydrins with N-halosuccinimide in aqueous media. The efficiency of the reaction in water was significantly improved in the presence of sodium dodecyl sulphate as the surfactant. Full article
(This article belongs to the Special Issue Organic Reaction in Green Solvents)
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2700 KiB  
Article
Ionic Liquids as Solvents for Rhodium and Platinum Catalysts Used in Hydrosilylation Reaction
by Witold Zielinski, Rafal Kukawka, Hieronim Maciejewski and Marcin Smiglak
Molecules 2016, 21(9), 1115; https://doi.org/10.3390/molecules21091115 - 24 Aug 2016
Cited by 27 | Viewed by 6439 | Correction
Abstract
A group of imidazolium and pyridinium based ionic liquids has been synthetized, and their ability to dissolve and activate the catalysts used in hydrosilylation reaction of 1-octane and 1,1,1,3,5,5,5-heptamethyltrisiloxane was investigated. An organometallic catalyst as well as inorganic complexes of platinum and rhodium [...] Read more.
A group of imidazolium and pyridinium based ionic liquids has been synthetized, and their ability to dissolve and activate the catalysts used in hydrosilylation reaction of 1-octane and 1,1,1,3,5,5,5-heptamethyltrisiloxane was investigated. An organometallic catalyst as well as inorganic complexes of platinum and rhodium dissolved in ionic liquids were used, forming liquid solutions not miscible with the substrates or with the products of the reaction. The results show that application of such a simple biphasic catalytic system enables reuse of ionic liquid phase with catalysts in multiple reaction cycles reducing the costs and decreasing the amount of catalyst needed per mole of product. Full article
(This article belongs to the Special Issue Organic Reaction in Green Solvents)
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836 KiB  
Article
An Expeditious and Greener Synthesis of 2-Aminoimidazoles in Deep Eutectic Solvents
by Martina Capua, Serena Perrone, Filippo Maria Perna, Paola Vitale, Luigino Troisi, Antonio Salomone and Vito Capriati
Molecules 2016, 21(7), 924; https://doi.org/10.3390/molecules21070924 - 16 Jul 2016
Cited by 47 | Viewed by 8256
Abstract
A high-yield one-pot two-step synthesis of 2-aminoimidazoles (2-AI), exploiting an under-air heterocyclodehydration process between α-chloroketones and guanidine derivatives, and using deep eutectic solvents (DESs) as nonconventional, “green” and “innocent” reaction media, has been accomplished successfully. The combination of either glycerol or urea with [...] Read more.
A high-yield one-pot two-step synthesis of 2-aminoimidazoles (2-AI), exploiting an under-air heterocyclodehydration process between α-chloroketones and guanidine derivatives, and using deep eutectic solvents (DESs) as nonconventional, “green” and “innocent” reaction media, has been accomplished successfully. The combination of either glycerol or urea with choline chloride (ChCl) proved to be effective for decreasing the reaction time to about 4–6 h in contrast to the 10–12 h usually required for the same reaction run in toxic and volatile organic solvents and under an argon atmosphere. In addition, the use of the ChCl–urea as a DES also enables the direct isolation of triaryl-substituted 2-AI derivatives by means of a simple work-up procedure consisting in filtration and crystallization, and allows the recycle of the DES mixture. A plausible mechanism highlighting the potential role played by hydrogen bonding catalysis has also been illustrated. Full article
(This article belongs to the Special Issue Organic Reaction in Green Solvents)
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986 KiB  
Article
Green Technique-Solvent Free Microwave Synthesis and Antimicrobial Evaluation of New Thiopyridine Arabinosides
by Ibrahim A. Maghrabi, Saleh Alghamdi, Majed Alrobaian and Hany A. Eldeab
Molecules 2016, 21(4), 477; https://doi.org/10.3390/molecules21040477 - 19 Apr 2016
Cited by 9 | Viewed by 4480
Abstract
A green protocol has been applied to synthesize a novel series of 3-cyano-2-(tri-O-acetyl-β-d-arabinopyranosylthio)pyridines in a short reaction time, in higher yields and with simpler operations, when compared with the conventional heating method. Deacetylation of the obtained acetylated arabinosides produced [...] Read more.
A green protocol has been applied to synthesize a novel series of 3-cyano-2-(tri-O-acetyl-β-d-arabinopyranosylthio)pyridines in a short reaction time, in higher yields and with simpler operations, when compared with the conventional heating method. Deacetylation of the obtained acetylated arabinosides produced 2-(β-d-arabinopyranosylthio)-3-cyanopyridines. The structures of the obtained products were confirmed on the basis of spectroscopic data (FT-IR, 1D, 2D-NMR). The synthesized compounds were screened for the antimicrobial activity against a selection of Gram positive and Gram negative bacteria. Full article
(This article belongs to the Special Issue Organic Reaction in Green Solvents)
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495 KiB  
Article
New Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Benzotriazolium-Based Ionic Liquids under Solvent-Free Conditions
by Zhiqing Liu, Rong Ma, Dawei Cao and Chenjiang Liu
Molecules 2016, 21(4), 462; https://doi.org/10.3390/molecules21040462 - 07 Apr 2016
Cited by 22 | Viewed by 5507
Abstract
An efficient synthesis of novel 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) and their derivatives, using Brønsted acidic ionic liquid [C2O2BBTA][TFA] as a catalyst, from the condensation of aryl aldehyde, β-ketoester and urea was described. Reactions proceeded smoothly for 40 min under [...] Read more.
An efficient synthesis of novel 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) and their derivatives, using Brønsted acidic ionic liquid [C2O2BBTA][TFA] as a catalyst, from the condensation of aryl aldehyde, β-ketoester and urea was described. Reactions proceeded smoothly for 40 min under solvent-free conditions and gave the desirable products with good to excellent yields (up to 99%). The catalyst could be easily recycled and reused with similar efficacies for at least six cycles. Full article
(This article belongs to the Special Issue Organic Reaction in Green Solvents)
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Review

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3370 KiB  
Review
Water and Aqueous Mixtures as Convenient Alternative Media for Organoselenium Chemistry
by Claudio Santi, Raquel G. Jacob, Bonifacio Monti, Luana Bagnoli, Luca Sancineto and Eder J. Lenardão
Molecules 2016, 21(11), 1482; https://doi.org/10.3390/molecules21111482 - 06 Nov 2016
Cited by 31 | Viewed by 7023
Abstract
Even if water is the natural environment for bioorganic reactions, its use in organic chemistry is often severely limited by the high insolubility of the organic derivatives. In this review, we introduce some examples of the use of water to perform organoselenium chemistry. [...] Read more.
Even if water is the natural environment for bioorganic reactions, its use in organic chemistry is often severely limited by the high insolubility of the organic derivatives. In this review, we introduce some examples of the use of water to perform organoselenium chemistry. We mainly discuss the advantages of this medium when the recyclability is demonstrated and when the water can control the selectivity of a reaction or enhance the reaction rate. Full article
(This article belongs to the Special Issue Organic Reaction in Green Solvents)
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Other

508 KiB  
Correction
Correction: Zielinski, W., et al. Ionic Liquids as Solvents for Rhodium and Platinum Catalysts Used in Hydrosilylation Reaction. Molecules 2016, 21, 1115
by Witold Zielinski, Rafal Kukawka, Hieronim Maciejewski and Marcin Smiglak
Molecules 2017, 22(7), 1203; https://doi.org/10.3390/molecules22071203 - 18 Jul 2017
Viewed by 3143
Abstract
The authors are sorry to report that the yield of the hydrosilylation reaction in [P44414][NTf2] (1) IL with [RhCl(PPh3)3] was replaced with the yield reported for [P44414][NTf2] (1) IL with K2PtCl4 in their published paper [1]. [...]
Full article
(This article belongs to the Special Issue Organic Reaction in Green Solvents)
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