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Heterocyclic Carbene Catalysis
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Institute of Organic and Analytical Chemistry (ICOA), University of Orleans, UMR-CNRS 7311, BP 6759, Rue de Chartres, CEDEX 02, 45067 Orleans, France
INSA Rouen Normandie, Univ. Rouen Normandie, CNRS UMR 6014 COBRA, FR 3038, F-76000 Rouen, France
Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans et CNRS, UMR 7311, BP 6759, F-45067 Orléans, France
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Heterocyclic Carbene Catalysis

Abstract submission deadline
closed (31 January 2023)
Manuscript submission deadline
closed (30 April 2023)
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3763

Topic Information

Dear Colleagues,

Heterocyclic carbene catalysis is a powerful process that has experienced rapid development. In particular, N-heterocycle carbenes (NHC), which have been applied in wide areas of organic synthesis. Their use in catalysis for the formation of new bonds via umpolung or non-umpolung mechanisms has developed in the last decade, involving several intermediates and allowing a fairly wide use of this type of catalysis. Recent applications have been reported in total natural synthesis with stereo and regioselectivity. We believe that the use of these intermediates or ligands will increase.

This Topic aims to review new methods and recent developments for the synthesis of complexes with heterocyclic carbene ligands and their use for the synthesis of various molecules of interest.

Prof. Dr. Sabine Berteina-Raboin
Prof. Dr. Thierry Besson
Prof. Dr. Patrick Rollin
Topic Editors

Keywords

  • catalysis
  • natural products
  • total synthesis
  • heterocyclic carbenes
  • ligands
  • coordination chemistry
  • transition metal catalysis and organocatalysis
  • heterocyclic chemistry

Participating Journals

Journal Name Impact Factor CiteScore Launched Year First Decision (median) APC
Catalysts
catalysts 		4.501 5.5 2011 12.7 Days 2200 CHF
Chemistry
chemistry 		- - 2019 15 Days 1600 CHF
Inorganics
inorganics 		3.149 5.1 2013 13.6 Days 2000 CHF
Molbank
molbank 		- 0.8 1997 13.1 Days 500 CHF
Molecules
molecules 		4.927 5.9 1996 13.4 Days 2300 CHF
Polymers
polymers 		4.967 5.7 2009 12.4 Days 2400 CHF

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Published Papers (4 papers)

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Review
Recent Advances in the Synthesis of 3,4-Dihydropyran-2-Ones Organocatalyzed by N-Heterocyclic Carbenes
by
Camilo Morales-Manrique
,
Edwin A. Baquero
and
James Guevara-Pulido
Molecules 2023, 28(9), 3743; https://doi.org/10.3390/molecules28093743 - 26 Apr 2023
Viewed by 553
Abstract
In recent years, N-heterocyclic carbenes (NHC) have gained recognition as versatile molecules capable of acting as organocatalysts in various reactions, particularly through the activation of aldehydes via Breslow-type adducts. This organocatalytic activation has enabled the production of numerous 3,4-dihydropyran-2-ones and related derivatives. [...] Read more.
In recent years, N-heterocyclic carbenes (NHC) have gained recognition as versatile molecules capable of acting as organocatalysts in various reactions, particularly through the activation of aldehydes via Breslow-type adducts. This organocatalytic activation has enabled the production of numerous 3,4-dihydropyran-2-ones and related derivatives. In this review, we provide an overview of the production of 3,4-dihydropyran-2-ones and derivatives via organocatalytic processes involving NHCs over the past eight years. These processes involve the use of a diverse range of substrates, catalysts, and reaction conditions, which can be classified into [4+2]-and [3+3]-type cycloadditions, primarily aimed at synthesizing this skeleton due to its biological activity and multiple stereocenters. These processes are scaled up to the gram scale, and the resulting products are often directed towards epimerization and functionalization to produce more complex molecules with potential applications in the biological field. Finally, we provide a perspective and the future directions of this topic in organic synthesis. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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Communication
Crystal Structure of 2-[(1E)-2-(4-Fluorophenyl)diazenyl]-1H-imidazole
by
Thomas Gelbrich
,
Klaus Wurst
,
Paul Mayer
,
Herwig Schottenberger
and
Sven Nerdinger
Molbank 2023, 2023(1), M1571; https://doi.org/10.3390/M1571 - 01 Feb 2023
Viewed by 544
Abstract
The molecule of the title compound adopts a twisted geometry with a rotation of approximately 30° between the mean planes of the imidazole and phenyl rings. The crystal structure displays hydrogen bonded chains as a result of N–H···N interactions between the imidazole rings [...] Read more.
The molecule of the title compound adopts a twisted geometry with a rotation of approximately 30° between the mean planes of the imidazole and phenyl rings. The crystal structure displays hydrogen bonded chains as a result of N–H···N interactions between the imidazole rings of neighboring molecules. These H-bonded chains are assembled into flat molecular layers parallel to the (121) plane. Two intermolecular interactions, involving inversion-related molecules belonging to adjacent molecular layers, contribute significantly to the stabilization of the crystal. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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Article
Influence of Substituents in a Six-Membered Chelate Ring of HG-Type Complexes Containing an N→Ru Bond on Their Stability and Catalytic Activity
by
Kirill A. Vasilyev
,
Alexandra S. Antonova
,
Nikita S. Volchkov
,
Nikita A. Logvinenko
,
Eugeniya V. Nikitina
,
Mikhail S. Grigoriev
,
Anton P. Novikov
,
Vladimir V. Kouznetsov
,
Kirill B. Polyanskii
and
Fedor I. Zubkov
Molecules 2023, 28(3), 1188; https://doi.org/10.3390/molecules28031188 - 25 Jan 2023
Viewed by 896
Abstract
An efficient approach to the synthesis of olefin metathesis HG-type catalysts containing an N→Ru bond in a six-membered chelate ring was proposed. For the most part, these ruthenium chelates can be prepared easily and in high yields based on the interaction between 2-vinylbenzylamines [...] Read more.
An efficient approach to the synthesis of olefin metathesis HG-type catalysts containing an N→Ru bond in a six-membered chelate ring was proposed. For the most part, these ruthenium chelates can be prepared easily and in high yields based on the interaction between 2-vinylbenzylamines and Ind II (the common precursor for Ru-complex synthesis). It was demonstrated that the increase of the steric volume of substituents attached to the nitrogen atom and in the α-position of the benzylidene fragment leads to a dramatic decrease in the stability of the target ruthenium complexes. The bulkiest iPr substituent bonded to the nitrogen atom or to the α-position does not allow the closing of the chelate cycle. N,N-Diethyl-1-(2-vinylphenyl)propan-1-amine is a limiting case; its interaction with Ind II makes it possible to isolate the corresponding ruthenium chelate in a low yield (5%). Catalytic activity of the synthesized complexes was tested in RCM reactions and compared with α-unsubstituted catalysts obtained previously. The structural peculiarities of the final ruthenium complexes were thoroughly investigated using XRD and NMR analysis, which allowed making a reliable correlation between the structure of the complexes and their catalytic properties. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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Communication
Ultrasound Assisted One-Pot Synthesis of Novel 3-(Aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines in Water
by
Ayoub El Mahmoudi
,
Khalid Karrouchi
,
Hamza Tachallait
and
Khalid Bougrin
Molbank 2022, 2022(4), M1529; https://doi.org/10.3390/M1529 - 17 Dec 2022
Viewed by 821
Abstract
In this work, we present an efficient one-pot method for the synthesis of three new azo-isoxazoline derivatives (4a–c) from aromatic aldehydes, hydroxylamine hydrochloride and 4-(allyloxy)azobenzene. Thus, the azo-isoxazoline derivatives (4a–c) were synthesized via 1,3-dipolar cycloaddition [...] Read more.
In this work, we present an efficient one-pot method for the synthesis of three new azo-isoxazoline derivatives (4a–c) from aromatic aldehydes, hydroxylamine hydrochloride and 4-(allyloxy)azobenzene. Thus, the azo-isoxazoline derivatives (4a–c) were synthesized via 1,3-dipolar cycloaddition using sodium dichloroisocyanurate (SDIC) as an eco-friendly and inexpensive oxidizing agent under ultrasound cavitation in water as a green solvent. The desired compounds 4a–c were obtained in high to excellent yields of 75–90%. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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