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Keywords = electroorganic synthesis

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12 pages, 3861 KiB  
Article
Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach
by Letizia Sorti, Fiammetta Vitulano, Elia Cappellini, Fulvio Uggeri, Carlo Francesco Morelli, Guido Sello, Alessandro Minguzzi and Alberto Vertova
Molecules 2023, 28(14), 5555; https://doi.org/10.3390/molecules28145555 - 20 Jul 2023
Cited by 4 | Viewed by 2916
Abstract
The synthesis of iodinated compounds using cheap, simple, and green strategies is of fundamental importance. Iodination reactions are mainly used to synthesize useful intermediates, especially in the pharmaceutical field, where they are employed for the production of contrast media or of iodinated active [...] Read more.
The synthesis of iodinated compounds using cheap, simple, and green strategies is of fundamental importance. Iodination reactions are mainly used to synthesize useful intermediates, especially in the pharmaceutical field, where they are employed for the production of contrast media or of iodinated active pharmaceutical ingredients. Traditional synthetic methods suffer from the use of erosive, toxic, or hazardous reactants. Approaches which involve the use of molecular iodine as an iodinating agent require the addition of an oxidizing agent, which is often difficult to handle. Electrochemistry can offer a valid and green alternative by avoiding the addition of such oxidizing agents, transforming the iodine source in the active species through the use of electrons as the main reactants. Herein, we report the electrochemical iodination with the generation of iodinating species in situ in water by using iodides as the source of iodine atoms. First of all, the electrochemical behavior of iodide and iodine in water on carbonaceous anodes was studied and, after selecting the suitable potential, in situ electrochemical iodination was successfully applied to 5-hydroxyisophthalic acid and 5-sulfosalicylic acid, comparing the iodinating power of I2 and iodonium species. Full article
(This article belongs to the Special Issue Electrochemistry and Organometallic Catalysis: Themed Issue in Honor of the Great Contribution of Prof. Dr. Christian Amatore and Prof. Dr. Anny Jutand)
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20 pages, 9564 KiB  
Review
Recent Advances in Enantioselective Catalytic Electrochemical Organic Transformations
by Fabrizio Medici, Simonetta Resta, Stefano Andolina and Maurizio Benaglia
Catalysts 2023, 13(6), 944; https://doi.org/10.3390/catal13060944 - 28 May 2023
Cited by 8 | Viewed by 3725
Abstract
Different approaches can be undertaken to realise a stereoselective electrochemical synthesis. Significant contributions to enantioselective electrochemical organic synthesis have been reported and largely reviewed in recent years. However, the development of general strategies for the electrochemical enantiocontrol of a transformation still presents considerable [...] Read more.
Different approaches can be undertaken to realise a stereoselective electrochemical synthesis. Significant contributions to enantioselective electrochemical organic synthesis have been reported and largely reviewed in recent years. However, the development of general strategies for the electrochemical enantiocontrol of a transformation still presents considerable challenges; in particular, relatively few contributions of highly enantioselective catalytic electrochemical reactions have been reported to date. In this review article, the most recent examples of asymmetric electrochemical catalysis are discussed. The article is organised by the three types of enantioselective catalysis: metal-based catalysis, organocatalysis and biocatalysis; in each section, the most significant and recent advances are presented and discussed. Full article
(This article belongs to the Special Issue New Trends in Asymmetric Catalysis: Green and Sustainable Catalysts)
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15 pages, 3666 KiB  
Article
Electrochemical Bottom-Up Synthesis of Chiral Carbon Dots from L-Proline and Their Application as Nano-Organocatalysts in a Stereoselective Aldol Reaction
by Martina Bortolami, Ingrid Izabela Bogles, Cecilia Bombelli, Fabiana Pandolfi, Marta Feroci and Fabrizio Vetica
Molecules 2022, 27(16), 5150; https://doi.org/10.3390/molecules27165150 - 12 Aug 2022
Cited by 29 | Viewed by 4143
Abstract
Chirality is undoubtedly a fundamental property of nature since the different interactions of optically active molecules in a chiral environment are essential for numerous applications. Thus, in the field of asymmetric synthesis, the search for efficient, sustainable, cost-effective and recyclable chiral catalysts is [...] Read more.
Chirality is undoubtedly a fundamental property of nature since the different interactions of optically active molecules in a chiral environment are essential for numerous applications. Thus, in the field of asymmetric synthesis, the search for efficient, sustainable, cost-effective and recyclable chiral catalysts is still the main challenge in organic chemistry. The field of carbon dots (CDs) has experienced tremendous development in the last 15 years, including their applications as achiral catalysts. Thus, understanding the implications of chirality in CDs chemistry could be of utmost importance to achieving sustainable and biocompatible chiral nanocatalysts. An efficient and cost-effective electrochemical synthetic methodology for the synthesis of L-Proline-based chiral carbon dots (CCDs) and EtOH-derived L-Proline-based chiral carbon dots (CCDs) is herein reported. The electrochemical set-up and reaction conditions have been thoroughly optimised and their effects on CCDs size, photoluminescence, as well as catalytic activity have been investigated. The obtained CCDs have been successfully employed to catalyze an asymmetric aldol reaction, showing excellent results in terms of yield, diastereo- and enantioselectivity. Moreover, the sustainable nature of the CCDs was demonstrated by recycling the catalysts for up to 3 cycles without any loss of reactivity or stereoselectivity. Full article
(This article belongs to the Special Issue Electrochemistry and Organometallic Catalysis: Themed Issue in Honor of the Great Contribution of Prof. Dr. Christian Amatore and Prof. Dr. Anny Jutand)
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