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Cascade Catalysis

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

Deadline for manuscript submissions: closed (30 June 2016) | Viewed by 25879

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Guest Editor
Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci, 12/C, 87036 Arcavacata di Rende, Italy
Interests: new syntheses of high value added molecules through catalytic assembly of simple units; innovative syntheses of heterocyclic molecules of pharmaceutical; agrochemical; applicative interest; carbonylation chemistry; use of non-conventional solvents in organic synthesis; synthesis and semi-synthesis of bioactive compounds of pharmaceutical or agrochemical interest; synthesis of new materials for advanced applications; extraction; characterization; evaluation of the biological activity of bioactive principles from natural matrices
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Special Issue Information

Dear Colleagues,

“Cascade”, “tandem”, or “sequential” catalysis refers to domino processes that correspond to the concatenation between different catalytic cycles, in which the product of the first cycle becomes the substrate of the second catalytic cycle and so on. These processes represent a particular case of "cascade", "tandem", "domino", or "sequential" reactions, which are processes in which two or more chemical transformations take place under identical conditions, with the product obtained in the first transformation becoming the substrate of the subsequent transformation(s), eventually leading to the final product.

Although rather frequent in biological systems (where a substrate is subsequently transformed into the final metabolite through a sequence of biocatalytic steps promoted by different enzymes), tandem catalysis is still relatively rare in chemical systems. However, during recent years, it has acquired an increasing importance in organic synthesis. In fact, cascade catalytic processes combine the intrinsic advantages of a sequential transformation (the possibility to construct functionalized molecules in one step starting from simple and readily available building blocks, avoiding the isolation and purification of the intermediate(s) with evident practical advantages, in terms of efficiency, selectivity, as well as atom, step and energy economy) with those associated with a catalytic process (the possibility to perform an otherwise kinetically hindered reaction, under mild conditions and using only a small amount of a promoter species).

This Special Issue is devoted to recent developments in this very important and emerging area of research. The scope is broad, and includes the elaboration of novel catalysts for performing already known processes in a more efficient manner, as well as the development of new cascade catalytic methods for the synthesis of products of industrial interest and of fine chemicals, including bioactive compounds.

Prof. Dr. Bartolo Gabriele
Guest Editor

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Keywords

  • cascade catalysis
  • homogeneous catalysis
  • cascade reactions
  • organic synthesis

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Published Papers (4 papers)

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Research

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5046 KiB  
Communication
Pd@[nBu4][Br] as a Simple Catalytic System for N-Alkylation Reactions with Alcohols
by Bastien Cacciuttolo, Oana Pascu, Cyril Aymonier and Mathieu Pucheault
Molecules 2016, 21(8), 1042; https://doi.org/10.3390/molecules21081042 - 10 Aug 2016
Cited by 4 | Viewed by 5395
Abstract
Palladium nanoparticles, simply and briefly generated in commercial and cheap onium salts using supercritical carbon dioxide, have been found to be an effective catalytic system for additive free N-alkylation reaction using alcohols via cascade oxidation/condensation/reduction steps. Full article
(This article belongs to the Special Issue Cascade Catalysis)
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3762 KiB  
Article
Auto-Tandem Catalysis in Ionic Liquids: Synthesis of 2-Oxazolidinones by Palladium-Catalyzed Oxidative Carbonylation of Propargylic Amines in EmimEtSO4
by Raffaella Mancuso, Asif Maner, Ida Ziccarelli, Christian Pomelli, Cinzia Chiappe, Nicola Della Ca’, Lucia Veltri and Bartolo Gabriele
Molecules 2016, 21(7), 897; https://doi.org/10.3390/molecules21070897 - 8 Jul 2016
Cited by 24 | Viewed by 5247
Abstract
A convenient carbonylative approach to 2-oxazolidinone derivatives carried out using an ionic liquid (1-ethyl-3-methylimidazolium ethyl sulfate, EmimEtSO4) as the solvent is presented. It is based on the sequential concatenation of two catalytic cycles, both catalyzed by the same metal species (auto-tandem [...] Read more.
A convenient carbonylative approach to 2-oxazolidinone derivatives carried out using an ionic liquid (1-ethyl-3-methylimidazolium ethyl sulfate, EmimEtSO4) as the solvent is presented. It is based on the sequential concatenation of two catalytic cycles, both catalyzed by the same metal species (auto-tandem catalysis): the first cycle corresponds to the oxidative monoaminocarbonylation of the triple bond of propargylic amines to give the corresponding 2-ynamide intermediates, while the second one involves the cyclocarbonylation of the latter to yield 2-(2-oxooxazolidin-5-ylidene)-acetamides. Reactions are carried out using a simple catalytic system consisting of PdI2 in conjunction with an excess of KI, and the catalyst/solvent system could be recycled several times without appreciable loss of activity after extraction of the organic product with Et2O. Full article
(This article belongs to the Special Issue Cascade Catalysis)
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1017 KiB  
Communication
A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols
by Xufeng Hou, Zhenzhong Jing, Xiangbin Bai and Zhiyong Jiang
Molecules 2016, 21(7), 842; https://doi.org/10.3390/molecules21070842 - 27 Jun 2016
Cited by 5 | Viewed by 5553
Abstract
Reported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yields (up to 95%) with [...] Read more.
Reported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yields (up to 95%) with excellent regio- and enantio-selectivity (up to 99% ee). This modular combination, including Jones oxidation and asymmetric organocatalysis, has satisfactory compatibility and reliability even at a 20 mmol scale, albeit without intermediary purification. Full article
(This article belongs to the Special Issue Cascade Catalysis)
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Review

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5183 KiB  
Review
A Novel Strategy for Biomass Upgrade: Cascade Approach to the Synthesis of Useful Compounds via C-C Bond Formation Using Biomass-Derived Sugars as Carbon Nucleophiles
by Sho Yamaguchi and Toshihide Baba
Molecules 2016, 21(7), 937; https://doi.org/10.3390/molecules21070937 - 20 Jul 2016
Cited by 20 | Viewed by 8342
Abstract
Due to the depletion of fossil fuels, biomass-derived sugars have attracted increasing attention in recent years as an alternative carbon source. Although significant advances have been reported in the development of catalysts for the conversion of carbohydrates into key chemicals (e.g., degradation approaches [...] Read more.
Due to the depletion of fossil fuels, biomass-derived sugars have attracted increasing attention in recent years as an alternative carbon source. Although significant advances have been reported in the development of catalysts for the conversion of carbohydrates into key chemicals (e.g., degradation approaches based on the dehydration of hydroxyl groups or cleavage of C-C bonds via retro-aldol reactions), only a limited range of products can be obtained through such processes. Thus, the development of a novel and efficient strategy targeted towards the preparation of a range of compounds from biomass-derived sugars is required. We herein describe the highly-selective cascade syntheses of a range of useful compounds using biomass-derived sugars as carbon nucleophiles. We focus on the upgrade of C2 and C3 oxygenates generated from glucose to yield useful compounds via C-C bond formation. The establishment of this novel synthetic methodology to generate valuable chemical products from monosaccharides and their decomposed oxygenated materials renders carbohydrates a potential alternative carbon resource to fossil fuels. Full article
(This article belongs to the Special Issue Cascade Catalysis)
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