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Catalysts
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Catalytic Approaches to Selective Elaboration of Organic Molecules
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Catalytic Approaches to Selective Elaboration of Organic Molecules

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (31 March 2021) | Viewed by 17407

Special Issue Editors

Prof. Dr. Alfonso Iadonisi

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Guest Editor
Department of Chemical Sciences, Università degli Studi di Napoli Federico II, Naples, Italy
Interests: original approaches for selective modifications of carbohydrates and multi-functionalized compounds; new methods and strategies for oligosaccharide synthesis; original routes to bioactive targets
Special Issues, Collections and Topics in MDPI journals
Dr. Serena Traboni

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Guest Editor
Department of Chemical Sciences, Università degli Studi di Napoli Federico II, Naples, Italy
Interests: regioselective functionalization of carbohydrates; solvent-free reactions; orthogonal protecting groups; one-pot protection of carbohydrates; saccharide building blocks; semi-synthetic polysaccharides; regioselective modification of polysaccharides

Special Issue Information

Dear Colleagues,

Development of ever more selective processes in organic synthesis (in the terms of chemo-, regio-, or stereoselectivity) has a relevant impact in terms of sustainability. Innovative catalytic approaches endowed with some selectivity are indeed expected to be competitive with synthetic methods in the current state of art.

This Special Issue is devoted to this intriguing area of synthetic organic chemistry and both original research papers and reviews are welcomed. The scope is broad and ranges from the elaboration of novel catalysts to the development of new protocols or processes for the synthesis of either products with industrial interest or fine chemicals.

Prof. Alfonso Iadonisi
Dr. Serena Traboni
Guest Editors

Manuscript Submission Information

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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. Catalysts is an international peer-reviewed open access monthly journal published by MDPI.

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Keywords

  • Organic processes
  • organic synthesis
  • chemoselectivity
  • regioselectivity
  • stereoselectivity
  • catalytic process

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Published Papers (5 papers)

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Research

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18 pages, 5187 KiB  
Article
Single-Crystal-to-Single-Crystal Transformation and Catalytic Properties of New Hybrid Perhalidometallates
by Ali Rayes, Stephany Zárate-Roldán, Irene Ara, Manel Moncer, Necmi Dege, M. Concepción Gimeno, Brahim Ayed and Raquel P. Herrera
Catalysts 2021, 11(7), 758; https://doi.org/10.3390/catal11070758 - 23 Jun 2021
Cited by 3 | Viewed by 2265
Abstract
Two new organic–inorganic salts of perhalidometallates with protonated organic amine cations have been synthesized and characterized by X-ray diffraction and thermal analysis. (CHBMAH2)ZnBr4·3/2H2O 1 and (CHBMAH2)ZnCl4 4 [(CHBMAH2)2+: 1,3-cyclohexanebis(methylammonium)] [...] Read more.
Two new organic–inorganic salts of perhalidometallates with protonated organic amine cations have been synthesized and characterized by X-ray diffraction and thermal analysis. (CHBMAH2)ZnBr4·3/2H2O 1 and (CHBMAH2)ZnCl4 4 [(CHBMAH2)2+: 1,3-cyclohexanebis(methylammonium)] were obtained in single-crystal form. The crystal packing in all of the obtained compounds is governed by the formation of various non-covalent intermolecular forces between tetrahalidometallate anions and organic cations, assisted by water molecules in the hydrates. Hirshfeld surface analysis denotes that the most important contributions to the crystal packing are X···H/H···X (X: Cl, Br, I) and H···H interactions. Interestingly, the compound 1,3-cyclohexanebis(methylammonium)tetrachloridozincate (II) dihydrate, (CHBMAH2)ZnCl4·2H2O 2, undergoes thermally-triggered single-crystal-to-single-crystal (SCSC) transformation upon dehydration to produce a supramolecular solid compound, 1,3-cyclohexanebis(methylammonium) tetrachloridozincate (II), (CHBMAH2)ZnCl4 4. The SCSC transformation causes changes in the lattice parameters and a structural rearrangement. Furthermore, the catalytic properties of (CHBMAH2)ZnCl4·2H2O 2 and (CHBMAH2)CdI4·2H2O 3 have been explored in the acetalization process using various uncommon alcohols, beyond methanol or ethanol, for the first time in the literature, with outstanding results, and opening the door to the formation of alternative acetals. Full article
(This article belongs to the Special Issue Catalytic Approaches to Selective Elaboration of Organic Molecules)
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12 pages, 1791 KiB  
Article
Unconventional Gold-Catalyzed One-Pot/Multicomponent Synthesis of Propargylamines Starting from Benzyl Alcohols
by Stephany Zárate-Roldán, María Concepción Gimeno and Raquel P. Herrera
Catalysts 2021, 11(4), 513; https://doi.org/10.3390/catal11040513 - 19 Apr 2021
Cited by 7 | Viewed by 2950
Abstract
A formal homogeneous gold-catalyzed A3-coupling, starting from benzyl alcohols, is reported for the straightforward synthesis of propargylamines. This is the first process where these highly valuable compounds have been synthesized, starting from the corresponding alcohols in a one-pot oxidation procedure using [...] Read more.
A formal homogeneous gold-catalyzed A3-coupling, starting from benzyl alcohols, is reported for the straightforward synthesis of propargylamines. This is the first process where these highly valuable compounds have been synthesized, starting from the corresponding alcohols in a one-pot oxidation procedure using MnO2, followed by a HAuCl4·3H2O catalyzed multicomponent reaction. The final products are obtained with very good yields in short reaction times, which is of fundamental interest for the synthesis of pharmaceuticals. The usefulness and efficiency of our methodology is successfully compared against the same reaction starting from aldehydes. Full article
(This article belongs to the Special Issue Catalytic Approaches to Selective Elaboration of Organic Molecules)
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9 pages, 2685 KiB  
Article
Catalytic, Regioselective Sulfonylation of Carbohydrates with Dibutyltin Oxide under Solvent-Free Conditions
by Serena Traboni, Emiliano Bedini, Alfredo Landolfi, Giulia Vessella and Alfonso Iadonisi
Catalysts 2021, 11(2), 202; https://doi.org/10.3390/catal11020202 - 3 Feb 2021
Cited by 6 | Viewed by 3041
Abstract
A simple approach was developed for the solvent-free regioselective functionalization of carbohydrate polyols with 4-toluesulfonyl (tosyl) group, allowing the easy and quick activation of a saccharide site with a tosylate leaving group. The method is based on the use of catalytic dibutyltin oxide [...] Read more.
A simple approach was developed for the solvent-free regioselective functionalization of carbohydrate polyols with 4-toluesulfonyl (tosyl) group, allowing the easy and quick activation of a saccharide site with a tosylate leaving group. The method is based on the use of catalytic dibutyltin oxide and tetrabuylammonium bromide (TBAB), and a moderate excess of N,N-diisopropylethyl amine (DIPEA) and tosyl chloride (TsCl), leading to the selective functionalization at 75 °C of a secondary equatorial hydroxy function flanked by an axial one in a pyranoside. The procedure is endowed with several advantages, such as the use of cheap reagents, experimental simplicity, and the need for reduced reaction times in comparison with other known approaches. Full article
(This article belongs to the Special Issue Catalytic Approaches to Selective Elaboration of Organic Molecules)
12 pages, 1657 KiB  
Article
Indole C6 Functionalization of Tryprostatin B Using Prenyltransferase CdpNPT
by Eric D. Gardner, Dustin A. Dimas, Matthew C. Finneran, Sara M. Brown, Anthony W. Burgett and Shanteri Singh
Catalysts 2020, 10(11), 1247; https://doi.org/10.3390/catal10111247 - 28 Oct 2020
Cited by 10 | Viewed by 3254
Abstract
Tryprostatin A and B are prenylated, tryptophan-containing, diketopiperazine natural products, displaying cytotoxic activity through different mechanisms of action. The presence of the 6-methoxy substituent on the indole moiety of tryprostatin A was shown to be essential for the dual inhibition of topoisomerase II [...] Read more.
Tryprostatin A and B are prenylated, tryptophan-containing, diketopiperazine natural products, displaying cytotoxic activity through different mechanisms of action. The presence of the 6-methoxy substituent on the indole moiety of tryprostatin A was shown to be essential for the dual inhibition of topoisomerase II and tubulin polymerization. However, the inability to perform late-stage modification of the indole ring has limited the structure–activity relationship studies of this class of natural products. Herein, we describe an efficient chemoenzymatic approach for the late-stage modification of tryprostatin B using a cyclic dipeptide N-prenyltransferase (CdpNPT) from Aspergillus fumigatus, which generates novel analogs functionalized with allylic, benzylic, heterocyclic, and diene moieties. Notably, this biocatalytic functionalizational study revealed high selectivity for the indole C6 position. Seven of the 11 structurally characterized analogs were exclusively C6-alkylated, and the remaining four contained predominant C6-regioisomers. Of the 24 accepted substrates, 10 provided >50% conversion and eight provided 20–50% conversion, with the remaining six giving <20% conversion under standard conditions. This study demonstrates that prenyltransferase-based late-stage diversification enables direct access to previously inaccessible natural product analogs. Full article
(This article belongs to the Special Issue Catalytic Approaches to Selective Elaboration of Organic Molecules)
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Review

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23 pages, 6533 KiB  
Review
Solvent-Free Approaches in Carbohydrate Synthetic Chemistry: Role of Catalysis in Reactivity and Selectivity
by Serena Traboni, Emiliano Bedini, Giulia Vessella and Alfonso Iadonisi
Catalysts 2020, 10(10), 1142; https://doi.org/10.3390/catal10101142 - 3 Oct 2020
Cited by 14 | Viewed by 4949
Abstract
Owing to their abundance in biomass and availability at a low cost, carbohydrates are very useful precursors for products of interest in a broad range of scientific applications. For example, they can be either converted into basic chemicals or used as chiral precursors [...] Read more.
Owing to their abundance in biomass and availability at a low cost, carbohydrates are very useful precursors for products of interest in a broad range of scientific applications. For example, they can be either converted into basic chemicals or used as chiral precursors for the synthesis of potentially bioactive molecules, even including nonsaccharide targets; in addition, there is also a broad interest toward the potential of synthetic sugar-containing structures in the field of functional materials. Synthetic elaboration of carbohydrates, in both the selective modification of functional groups and the assembly of oligomeric structures, is not trivial and often entails experimentally demanding approaches practiced by specialized groups. Over the last years, a large number of solvent-free synthetic methods have appeared in the literature, often being endowed with several advantages such as greenness, experimental simplicity, and a larger scope than analogous reactions in solution. Most of these methods are catalytically promoted, and the catalyst often plays a key role in the selectivity associated with the process. This review aims to describe the significant recent contributions in the solvent-free synthetic chemistry of carbohydrates, devoting a special critical focus on both the mechanistic role of the catalysts employed and the differences evidenced so far with corresponding methods in solution. Full article
(This article belongs to the Special Issue Catalytic Approaches to Selective Elaboration of Organic Molecules)
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