Organocatalysis in the Chemical Transformations, 2nd Edition

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: 30 April 2024 | Viewed by 2056

Special Issue Editors


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Instituto Nacional de Metrologia, Qualidade e Tecnologia (INMETRO), Duque de Caxias, RJ, Brazil
Interests: heterogeneous catalysis; catalysts synthesis; CO2 conversion; biomass conversion and sustainable process; graphene-based catalysts; supported-organocatalysts; nanometrology applied to catalysts
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Centre of Excellence for Research in Sustainable Chemistry, Department of Chemistry, Federal University of São Carlos, São Carlos 13565-905, SP, Brazil
Interests: green chemistry; organocatalysis; photocatalysis; heterogeneous catalysis; flow chemistry; medicinal chemistry

Special Issue Information

Dear Colleagues,

Following the first successful Special Issue on this topic (available here), we are happy to announce a second edition entitled “Organocatalysis in the Chemical Transformations, 2nd Edition”.

Organocatalysis represents a breakthrough in chemical transformations, offering innovation, superior activity, selectivity and, notably, a sustainable approach at a relatively low cost. It relies on the use of small organic molecules (isolated or attached to supports) with a huge range of applications, including fine chemistry, novel molecule synthesis, storage energy components, and photoredox and electrocatalytics processes. Organocatalysis was recognized as a tool for controlling the chirality of molecules by the Nobel Prize in Chemistry 2021, which was awarded for "the development of asymmetric organocatalysis."

Despite all of these advantages, novel organocatalysts must be designed to meet the requirements of large-scale production. A combination of organic molecules with heterogeneous supports can advance manufacturing under the industrial perspective.

This Special Issue is dedicated to organocatalysis, aiming to provide further insight into organocatalysis research and positively contribute to the progression of this field. Therefore, our colleagues are invited to submit their valuable research to this Special Issue, including experimental and theoretical results.

Dr. Adriana Maria da Silva
Dr. Arlene G. Corrêa
Guest Editors

Manuscript Submission Information

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Keywords

  • organocatalysis
  • heterogeneous organocatalysis
  • organocatalyzed reactions
  • metallo-organocatalysis
  • chiral
  • asymmetric
  • computational development

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Published Papers (2 papers)

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Research

17 pages, 4421 KiB  
Article
Synthesis and Catalytic Activity of 1,2-Benzenediamine-Derived Organocatalysts Based on (1R,2R)-Cyclohexane-1,2-Diamine
by Luka Ciber, Klara Klemenčič, Ana Golob, Helena Brodnik, Franc Požgan, Jurij Svete, Bogdan Štefane and Uroš Grošelj
Catalysts 2024, 14(4), 274; https://0-doi-org.brum.beds.ac.uk/10.3390/catal14040274 - 18 Apr 2024
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Abstract
A four-step synthesis process of bifunctional, noncovalent organocatalysts based on the chiral (1R,2R)-cyclohexane-1,2-diamine scaffold containing a 1,2-benzenediamine H-bond donor was developed. Nucleophilic aromatic substitution of the 2-fluoronitrobenzene derivative with the commercial (1R,2R)-cyclohexane-1,2-diamine was followed by [...] Read more.
A four-step synthesis process of bifunctional, noncovalent organocatalysts based on the chiral (1R,2R)-cyclohexane-1,2-diamine scaffold containing a 1,2-benzenediamine H-bond donor was developed. Nucleophilic aromatic substitution of the 2-fluoronitrobenzene derivative with the commercial (1R,2R)-cyclohexane-1,2-diamine was followed by selective alkylation of the primary amino group, reduction of the aromatic nitro group and final derivatization of the primary aromatic amino group, i.e., acylation, sulfonation, reductive alkylation and arylation, leading to the four subtypes of organocatalysts. All new compounds were fully characterized. The prepared organocatalysts (32 examples) were tested in the Michael addition of acetylacetone to trans-β-nitrostyrene, yielding the addition product with incomplete conversions (up to 93%) and enantioselectivities of up to 41% ee. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations, 2nd Edition)
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10 pages, 2578 KiB  
Communication
Aminocyclopropenium as a New Class of Hydrogen Bonding Catalyst in Friedel–Crafts Alkylation
by Xuesuo Ma, Jiaxi Xu, Jingjing Liu, Jun He, Tong Chang, Qingbiao Yang, Ning Li, Dong Qian and Zhenjiang Li
Catalysts 2023, 13(10), 1370; https://0-doi-org.brum.beds.ac.uk/10.3390/catal13101370 - 16 Oct 2023
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Abstract
H-bonding has achieved massive advancements by utilizing an H-bond donor (HBD) to interact with the electron-rich site of the substrate, and an H-bond acceptor (HBA) to coordinate with the electron-deficient site. Rapid transformation is often correlated with the acidity of HBD, namely the [...] Read more.
H-bonding has achieved massive advancements by utilizing an H-bond donor (HBD) to interact with the electron-rich site of the substrate, and an H-bond acceptor (HBA) to coordinate with the electron-deficient site. Rapid transformation is often correlated with the acidity of HBD, namely the degree of charge deficiency of the hydrogen proton. In addition, the positive cations were employed to enhance the HBD; the electron-withdrawing groups were also a dissimilar approach for increasing the capability of the H-bond donor. We first introduced the H-bonding organic ion pair tris(phenylamino)cyclopropenium (TPAC·Cl) into the Friedel–Crafts alkylation of indoles with nitroalkenes, which was implemented via vicinal positive charges on the cyclopropenium core. The counter ion chloride anion became a potential HBA to activate the electron-deficient part of the substrate. X-ray analyses of a single crystal of TPAC·Cl described the 3D architecture and the delocalized cationic charge in the solid state. The aromatic cyclopropenium endowed the N–H moieties with the ability of the H-bond donor to activate the nitroalkene; meanwhile, the chloride anion acted as the H-bond acceptor to activate the indole. The amino-cyclopropenium-offered HBD and HBA displayed cooperative organocatalysis in the Friedel–Crafts alkylation of indole with nitroalkene. A new class of hydrogen bonding catalysis and a working mechanism were proposed. Full article
(This article belongs to the Special Issue Organocatalysis in the Chemical Transformations, 2nd Edition)
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