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Organic Reactions in Deep Eutectic Solvents
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Organic Reactions in Deep Eutectic Solvents

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

Deadline for manuscript submissions: closed (29 February 2024) | Viewed by 10810

Special Issue Editors

Prof. Dr. Gabriela Guillena

E-Mail Website
Guest Editor
Organic Chemistry Department and Organic Synthesis Institute, Alicante University, P.O. Box 99, 03080 Alicante, Spain
Interests: organic synthesis; green chemistry; deep eutectic solvents; transition-metal catalysis; organocatalysis; enantioselective synthesis; polymer synthesis
Dr. Maria Luisa Di Gioia

E-Mail Website
Guest Editor
Dipartimento di Farmacia e Scienze della Salute e della Nutrizione, Università della Calabria, Arcavacata di Rende, Italy
Interests: mass spectrometry; bioconjugates; amino acids; peptide synthesis; organic synthesis; green chemistry; deep eutectic solvents
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The need for a more sustainable synthesis of organic compounds is undeniable. The replacement of volatile organic compounds (VOCs) as solvent media in organic transformations is crucial to access valuable organic products in an environmentally benign manner.

Among the neoteric solvents available for this purpose, Deep Eutectic Solvents (DES) have gained increased attention in recent years. Although eutectic mixtures have been known for centuries, it was not until 2003, when Andrew Abbott coined the term DES, that the use of these solvents started to be explored in several research fields. DESs, defined as mixtures of pure compounds for which the eutectic point temperature is below that of an ideal liquid mixture, meet the requirements to be considered as green solvents. Apart from the fact that they have a negligible boiling point, easy preparation, low cost, low toxicity, or high biodegradability, DESs also provide the possibility of tailoring their physicochemical properties to the chemical process, making this a relevant feature for organic synthesis. In addition, most DESs are obtained through a simple extraction with water, allowing the easy separation of the organic products from the DES. However, if catalysts are needed for the transformation, the catalyst/DES system can be designed to recover the catalysts after the reaction has taken place. Furthermore, some unique properties such as gas solubility and the stability of radical intermediates have provided the opportunity to discover novel reactivities.

In this Special Issue, we intend to compile the latest achievements in the use of DESs in organic transformations as the solvent media. Especially in catalyzed reactions, whether a DES is used as a solvent or as the catalyst, the focus will be on its possible recycling and reuse. The goal of this Special Issue will be to advance the state-of-the-art in this field and further explore the new prospects offered by DESs in organic synthesis.

Prof. Dr. Gabriela Guillena
Dr. Maria Luisa Di Gioia
Guest Editors

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Keywords

  • organic synthesis
  • green chemistry
  • biocatalysis
  • organocatalysis
  • transition-metal catalysis
  • recyclability

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Published Papers (6 papers)

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Research

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10 pages, 1471 KiB  
Article
A Sustainable Synthetic Approach to Tacrine and Cholinesterase Inhibitors in Deep Eutectic Solvents under Aerobic Conditions
by Luciana Cicco, Filippo Maria Perna, Vito Capriati and Paola Vitale
Molecules 2024, 29(6), 1399; https://doi.org/10.3390/molecules29061399 - 21 Mar 2024
Cited by 3 | Viewed by 1446
Abstract
An enhanced, sustainable, and efficient method for synthesizing tacrine, achieving a 98% yield, has been developed by replacing volatile organic compounds with more eco-friendly solvents such as deep eutectic solvent (DESs). The optimized protocol scales easily to 3 g of substrate without yield [...] Read more.
An enhanced, sustainable, and efficient method for synthesizing tacrine, achieving a 98% yield, has been developed by replacing volatile organic compounds with more eco-friendly solvents such as deep eutectic solvent (DESs). The optimized protocol scales easily to 3 g of substrate without yield loss and extends successfully to tacrine derivatives with reduced hepatotoxicity. Particularly notable is the synthesis of novel triazole-based derivatives, yielding 90–95%, by integrating an in situ preparation of aryl azides in DESs with N-propargyl-substituted tacrine derivatives. Quantitative metrics validate the green aspects of the reported drug development processes. Full article
(This article belongs to the Special Issue Organic Reactions in Deep Eutectic Solvents)
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13 pages, 8618 KiB  
Article
Enantioselective Catalytic Aldol Reactions in the Presence of Knoevenagel Nucleophiles: A Chemoselective Switch Optimized in Deep Eutectic Solvents Using Mechanochemistry
by Hanaa Al Beiruty, Sofiia-Stefaniia Zhylinska, Nino Kutateladze, Hayley Kay Tinn Cheong, José A. Ñíguez, Sarah J. Burlingham, Xavier Marset, Gabriela Guillena, Rafael Chinchilla, Diego A. Alonso and Thomas C. Nugent
Molecules 2024, 29(1), 4; https://doi.org/10.3390/molecules29010004 - 19 Dec 2023
Viewed by 2085
Abstract
In the presence of different nucleophilic Knoevenagel competitors, cyclic and acyclic ketones have been shown to undergo highly chemoselective aldol reactions with aldehydes. In doing so, the substrate breadth for this emerging methodology has been significantly broadened. The method is also no longer [...] Read more.
In the presence of different nucleophilic Knoevenagel competitors, cyclic and acyclic ketones have been shown to undergo highly chemoselective aldol reactions with aldehydes. In doing so, the substrate breadth for this emerging methodology has been significantly broadened. The method is also no longer beholden to proline-based catalyst templates, e.g., commercially available O-t-Bu-L-threonine is advantageous for acyclic ketones. The key insight was to exploit water-based mediums under conventional (in-water) and non-conventional (deep eutectic solvents) conditions. With few exceptions, high aldol-to-Knoevenagel chemoselectivity (>10:1) and good product profiles (yield, dr, and ee) were observed, but only in DESs (deep eutectic solvents) in conjunction with ball milling did short reaction times occur. Full article
(This article belongs to the Special Issue Organic Reactions in Deep Eutectic Solvents)
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9 pages, 901 KiB  
Article
Synthesis of Mixed Chitin Esters via Acylation of Chitin in Deep Eutectic Solvents
by Yusuke Egi and Jun-ichi Kadokawa
Molecules 2023, 28(24), 8132; https://doi.org/10.3390/molecules28248132 - 16 Dec 2023
Cited by 2 | Viewed by 1333
Abstract
The development of efficient derivatization methods of chitin, such as acylation, has been identified to confer new properties and functions to chitin. In this study, we investigate the synthesis of mixed chitin esters via the acylation of chitin in deep eutectic solvents (DESs) [...] Read more.
The development of efficient derivatization methods of chitin, such as acylation, has been identified to confer new properties and functions to chitin. In this study, we investigate the synthesis of mixed chitin esters via the acylation of chitin in deep eutectic solvents (DESs) comprising 1-allyl-3-methylimidazolum chloride and 1,1,3,3-tetramethylguanidine based on a previous study that reported the development of efficient acylation of chitin in the DES to obtain single chitin esters. A stearoyl group was selected as the first substituent, which was combined with several bulky acyl and long oleoyl groups as the second substituents. After dissolution of chitin in the DES (2 wt%), the acylation reactions were conducted using stearoyl and the desired acyl chlorides for 1 h + 24 h at 100 °C in the resulting solutions. The IR and 1H NMR spectra of the isolated products confirmed the structures of mixed chitin esters with two different substituents. The substituent ratios in the derivatives, which were estimated via the 1H NMR analysis, were changed according to the feed ratios of two acyl chlorides. Full article
(This article belongs to the Special Issue Organic Reactions in Deep Eutectic Solvents)
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13 pages, 1776 KiB  
Article
Nickel-Imidazolium Low Transition Temperature Mixtures with Lewis-Acidic Character
by Mario Martos and Isidro M. Pastor
Molecules 2023, 28(17), 6338; https://doi.org/10.3390/molecules28176338 - 30 Aug 2023
Viewed by 979
Abstract
Low transition temperature mixtures (LTTMs) are a new generation of solvents that have found extensive application in organic synthesis. The interactions between the components often generate highly activated, catalytically active species, thus opening the possibility of using LTTMs as catalysts, rather than solvents. [...] Read more.
Low transition temperature mixtures (LTTMs) are a new generation of solvents that have found extensive application in organic synthesis. The interactions between the components often generate highly activated, catalytically active species, thus opening the possibility of using LTTMs as catalysts, rather than solvents. In this work, we introduce a nickel-based imidazolium LTTM, study its thermal behavior and explore its catalytic activity in the solvent-free allylation of heterocycles with allylic alcohols. This system is effective in this reaction, affording the corresponding products in excellent yield without the need for additional purifications, thus resulting in a very environmentally friendly protocol. Full article
(This article belongs to the Special Issue Organic Reactions in Deep Eutectic Solvents)
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Review

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22 pages, 5937 KiB  
Review
Recent Advancements in the Utilization of s-Block Organometallic Reagents in Organic Synthesis with Sustainable Solvents
by María Jesús Rodríguez-Álvarez, Nicolás Ríos-Lombardía, Sergio E. García-Garrido, Carmen Concellón, Vicente del Amo, Vito Capriati and Joaquín García-Álvarez
Molecules 2024, 29(7), 1422; https://doi.org/10.3390/molecules29071422 - 22 Mar 2024
Cited by 1 | Viewed by 1347
Abstract
This mini-review offers a comprehensive overview of the advancements made over the last three years in utilizing highly polar s-block organometallic reagents (specifically, RLi, RNa and RMgX compounds) in organic synthesis run under bench-type reaction conditions. These conditions involve exposure to air/moisture [...] Read more.
This mini-review offers a comprehensive overview of the advancements made over the last three years in utilizing highly polar s-block organometallic reagents (specifically, RLi, RNa and RMgX compounds) in organic synthesis run under bench-type reaction conditions. These conditions involve exposure to air/moisture and are carried out at room temperature, with the use of sustainable solvents as reaction media. In the examples provided, the adoption of Deep Eutectic Solvents (DESs) or even water as non-conventional and protic reaction media has not only replicated the traditional chemistry of these organometallic reagents in conventional and toxic volatile organic compounds under Schlenk-type reaction conditions (typically involving low temperatures of −78 °C to 0 °C and a protective atmosphere of N2 or Ar), but has also resulted in higher conversions and selectivities within remarkably short reaction times (measured in s/min). Furthermore, the application of the aforementioned polar organometallics under bench-type reaction conditions (at room temperature/under air) has been extended to other environmentally responsible reaction media, such as more sustainable ethereal solvents (e.g., CPME or 2-MeTHF). Notably, this innovative approach contributes to enhancing the overall sustainability of s-block-metal-mediated organic processes, thereby aligning with several key principles of Green Chemistry. Full article
(This article belongs to the Special Issue Organic Reactions in Deep Eutectic Solvents)
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27 pages, 6640 KiB  
Review
N-, O- and S-Heterocycles Synthesis in Deep Eutectic Solvents
by Serena Perrone, Francesco Messa, Luigino Troisi and Antonio Salomone
Molecules 2023, 28(8), 3459; https://doi.org/10.3390/molecules28083459 - 14 Apr 2023
Cited by 12 | Viewed by 2894
Abstract
The synthesis of heterocycles is a fundamental area of organic chemistry that offers enormous potential for the discovery of new products with important applications in our daily life such as pharmaceuticals, agrochemicals, flavors, dyes, and, more generally, engineered materials with innovative properties. As [...] Read more.
The synthesis of heterocycles is a fundamental area of organic chemistry that offers enormous potential for the discovery of new products with important applications in our daily life such as pharmaceuticals, agrochemicals, flavors, dyes, and, more generally, engineered materials with innovative properties. As heterocyclic compounds find application across multiple industries and are prepared in very large quantities, the development of sustainable approaches for their synthesis has become a crucial objective for contemporary green chemistry committed to reducing the environmental impact of chemical processes. In this context, the present review focuses on the recent methodologies aimed at preparing N-, O- and S-heterocyclic compounds in Deep Eutectic Solvents, a new class of ionic solvents that are non-volatile, non-toxic, easy to prepare, easy to recycle, and can be obtained from renewable sources. Emphasis has been placed on those processes that prioritize the recycling of catalyst and solvent, as they offer the dual benefit of promoting synthetic efficiency while demonstrating environmental responsibility. Full article
(This article belongs to the Special Issue Organic Reactions in Deep Eutectic Solvents)
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