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Solvent-Dependent Organic Transformations
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Solvent-Dependent Organic Transformations

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

Deadline for manuscript submissions: closed (30 June 2020) | Viewed by 16273

Special Issue Editor

Dr. Alejandro Baeza Carratalá

E-Mail Website
Guest Editor
Organic Chemistry Department and Instituto de Síntesis Orgánica, Universitat d’Alacant, 03690 Alicante, Spain
Interests: asymmetric catalysis; green chemistry; organocatalysis; metal catalysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Solvents are ubiquitous in organic chemistry transformations since they are the medium where the reaction occurs. The main features of solvents are, among others, the easy control of mass and heat transference, the stabilization of transition sates, and the modification of reactivity (rate, selectivity, etc.). For these reasons, the selection of the appropriate solvent for a particular organic reaction is crucial and must be performed conscientiously.
In this context, the aim of this Special Issue is to collect articles describing organic transformations in which solvents play an important and demonstrated role, and do not merely acting as a spectator. Therefore, works in which the solvent itself can promote or facilitate the transformation or where it has a clear influence on the outcome of the transformation, in terms of yield, regio- and/or stereoselectivity, or even studies of the effect of a solvent on a particular reaction will be covered in this Special Issue.

Dr. Alejandro Baeza Carratalá
Guest Editor

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Keywords

  • Solvent effects
  • Promoters
  • Organic transformations
  • Organic synthesis
  • Reaction mechanisms

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Published Papers (3 papers)

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Research

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12 pages, 2319 KiB  
Article
HFIP-Promoted Synthesis of Substituted Tetrahydrofurans by Reaction of Epoxides with Electron-Rich Alkenes
by Natalia Llopis and Alejandro Baeza
Molecules 2020, 25(15), 3464; https://doi.org/10.3390/molecules25153464 - 30 Jul 2020
Cited by 11 | Viewed by 4136
Abstract
In the present work, the employment of fluorinated alcohols, specifically 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), as solvent and promoter of the catalyst-free synthesis of substituted tetrahydrofuranes through the addition of electron-rich alkenes to epoxydes is described. The unique properties of this fluorinated alcohol, which is very [...] Read more.
In the present work, the employment of fluorinated alcohols, specifically 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), as solvent and promoter of the catalyst-free synthesis of substituted tetrahydrofuranes through the addition of electron-rich alkenes to epoxydes is described. The unique properties of this fluorinated alcohol, which is very different from their non-fluorinated analogs, allows carrying out this new straightforward protocol under smooth reaction conditions affording the corresponding adducts in moderate yields in the majority of cases. Remarkably, this methodology has allowed the synthesis of new tetrahydrofuran-based spiro compounds as well as tetrahydrofurobenzofuran derivatives. The scope and limitations of the process are also discussed. Mechanistic studies were also performed pointing towards a purely ionic or a SN2-type process depending on the nucleophilicity of the alkene employed. Full article
(This article belongs to the Special Issue Solvent-Dependent Organic Transformations)
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12 pages, 3726 KiB  
Article
Base-Promoted Chemodivergent Formation of 1,4-Benzoxazepin-5(4H)-ones and 1,3-Benzoxazin-4(4H)-ones Switched by Solvents
by Qian Chen, Yunpeng Wang and Ruimao Hua
Molecules 2019, 24(20), 3773; https://doi.org/10.3390/molecules24203773 - 19 Oct 2019
Cited by 14 | Viewed by 3844
Abstract
The KOH-promoted chemodivergent benzannulation of ortho-fluorobenzamides with 2-propyn-1-ol can afford either 1,4-benzoxazepin-5(4H)-ones or 1,3-benzoxazin-4(4H)-ones in good yields with high selectivity, depending greatly upon the use of solvents. In the case of using DMSO, the intermolecular benzannulation produced seven-membered [...] Read more.
The KOH-promoted chemodivergent benzannulation of ortho-fluorobenzamides with 2-propyn-1-ol can afford either 1,4-benzoxazepin-5(4H)-ones or 1,3-benzoxazin-4(4H)-ones in good yields with high selectivity, depending greatly upon the use of solvents. In the case of using DMSO, the intermolecular benzannulation produced seven-membered benzo-fused heterocycles of 1,4-benzoxazepin-5(4H)-ones, whereas in MeCN, the six-membered benzo-fused heterocycles of 1,3-benzoxazin-4(4H)-ones were formed. The KOH-promoted benzannulation proceeded most probably through the C–F nucleophilic substitution of ortho-fluorobenzamides with 2-propyn-1-ol to give the intermediate of ortho-[(2-propynyl)oxy]benzamide, which underwent the intramolecular hydroamidation in a different manner to afford either seven- or six-membered benzo-fused heterocycles. Full article
(This article belongs to the Special Issue Solvent-Dependent Organic Transformations)
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Review

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18 pages, 5824 KiB  
Review
Recent Progress of Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions (CuAAC) in Sustainable Solvents: Glycerol, Deep Eutectic Solvents, and Aqueous Media
by Noel Nebra and Joaquín García-Álvarez
Molecules 2020, 25(9), 2015; https://doi.org/10.3390/molecules25092015 - 26 Apr 2020
Cited by 60 | Viewed by 7419
Abstract
This mini-review presents a general overview of the progress achieved during the last decade on the amalgamation of CuAAC processes (copper-catalyzed azide-alkyne cycloaddition) with the employment of sustainable solvents as reaction media. In most of the presented examples, the use of water, glycerol [...] Read more.
This mini-review presents a general overview of the progress achieved during the last decade on the amalgamation of CuAAC processes (copper-catalyzed azide-alkyne cycloaddition) with the employment of sustainable solvents as reaction media. In most of the presented examples, the use of water, glycerol (Gly), or deep eutectic solvents (DESs) as non-conventional reaction media allowed not only to recycle the catalytic system (thus reducing the amount of the copper catalyst needed per mole of substrate), but also to achieve higher conversions and selectivities when compared with the reaction promoted in hazardous and volatile organic solvents (VOCs). Moreover, the use of the aforementioned green solvents also permits the improvement of the overall sustainability of the Cu-catalyzed 1,3-dipolar cycloaddition process, thus fulfilling several important principles of green chemistry. Full article
(This article belongs to the Special Issue Solvent-Dependent Organic Transformations)
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