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Special Issue "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)

Special Issue Editors

Guest Editor
Dr. Joaquín García Álvarez

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
Website | E-Mail
Interests: metal-catalyzed organic reactions;homogeneous catalysis;green solvents;atom economy;deep eutectic solvents (dess);water;glycerol;main-group mediated organic reactions
Guest Editor
Dr. Jonathan Sperry

School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand
Website | E-Mail
Interests: C–H functionalization; sustainable synthesis; biomass-derived building blocks; green solvents; chromatography-free synthesis

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

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 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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Open AccessEditorial Special Issue: “Organic Reactions in Green Solvents”
Molecules 2016, 21(11), 1527; doi:10.3390/molecules21111527
Received: 3 November 2016 / Accepted: 9 November 2016 / Published: 15 November 2016
Cited by 3 | PDF Full-text (154 KB) | HTML Full-text | XML Full-text
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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Open AccessArticle Transformation of Tertiary Benzyl Alcohols into the Vicinal Halo-Substituted Derivatives Using N-Halosuccinimides
Molecules 2016, 21(10), 1325; doi:10.3390/molecules21101325
Received: 31 August 2016 / Revised: 23 September 2016 / Accepted: 27 September 2016 / Published: 2 October 2016
Cited by 1 | PDF Full-text (985 KB) | HTML Full-text | XML Full-text | Supplementary Files
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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Open AccessArticle Ionic Liquids as Solvents for Rhodium and Platinum Catalysts Used in Hydrosilylation Reaction
Molecules 2016, 21(9), 1115; doi:10.3390/molecules21091115
Received: 28 June 2016 / Revised: 8 August 2016 / Accepted: 12 August 2016 / Published: 24 August 2016
Cited by 3 | PDF Full-text (2700 KB) | HTML Full-text | XML Full-text | 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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Open AccessArticle An Expeditious and Greener Synthesis of 2-Aminoimidazoles in Deep Eutectic Solvents
Molecules 2016, 21(7), 924; doi:10.3390/molecules21070924
Received: 1 July 2016 / Revised: 11 July 2016 / Accepted: 13 July 2016 / Published: 16 July 2016
Cited by 10 | PDF Full-text (836 KB) | HTML Full-text | XML Full-text | Supplementary Files
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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Open AccessArticle Green Technique-Solvent Free Microwave Synthesis and Antimicrobial Evaluation of New Thiopyridine Arabinosides
Molecules 2016, 21(4), 477; doi:10.3390/molecules21040477
Received: 28 February 2016 / Revised: 30 March 2016 / Accepted: 1 April 2016 / Published: 19 April 2016
Cited by 1 | PDF Full-text (986 KB) | HTML Full-text | XML Full-text
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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Open AccessArticle New Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Benzotriazolium-Based Ionic Liquids under Solvent-Free Conditions
Molecules 2016, 21(4), 462; doi:10.3390/molecules21040462
Received: 13 March 2016 / Revised: 30 March 2016 / Accepted: 5 April 2016 / Published: 7 April 2016
Cited by 3 | PDF Full-text (495 KB) | HTML Full-text | XML Full-text
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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Open AccessReview Water and Aqueous Mixtures as Convenient Alternative Media for Organoselenium Chemistry
Molecules 2016, 21(11), 1482; doi:10.3390/molecules21111482
Received: 20 October 2016 / Accepted: 2 November 2016 / Published: 6 November 2016
Cited by 2 | PDF Full-text (3370 KB) | HTML Full-text | XML Full-text
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.
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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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Figure 1

Other

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Open AccessCorrection Correction: Zielinski, W., et al. Ionic Liquids as Solvents for Rhodium and Platinum Catalysts Used in Hydrosilylation Reaction. Molecules 2016, 21, 1115
Molecules 2017, 22(7), 1203; doi:10.3390/molecules22071203
Received: 3 July 2017 / Accepted: 7 July 2017 / Published: 18 July 2017
PDF Full-text (508 KB) | HTML Full-text | XML Full-text
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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