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Catalysts for C–H Activation and Functionalisation
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Catalysts for C–H Activation and Functionalisation

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalytic Materials".

Deadline for manuscript submissions: closed (15 September 2020) | Viewed by 26275

Special Issue Editor

Prof. Dr. Immacolata Tommasi

E-Mail Website
Guest Editor
Dipartimento di Chimica, Università di Bari “A. Moro”, v. Orabona, 4, 70126 Bari, Italy
Interests: C–H activation; carbon dioxide; synthesis of carboxylic acids; transition–metal catalysis; Brønsted-base catalysis; carboxylation reactions; enzymatic catalysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Catalysts is planning a Special Issue focused on “Catalysts for C–H Activation and Functionalization”. In the 1970s, Shilov and Crabtree pioneered research in this fascinating field, reporting, respectively, methane functionalization and alkanes dehydrogenation promoted by soluble transition metal complexes. In the early 1980s, the groups of Bergman, Jones, and Graham provided evidence for C–H oxidative addition to Ir centers. Since then, C–H activation/functionalization chemistry has exhibited a steady growth and continues to expand to this day thanks to the development of advanced synthetic strategies that allow, for example, to control the positional selectivity in intermolecular C–H transformations. Research and findings in this research area were recently reviewed in the Chemical Review Special Issue titled “C–H activation” (reporting a comprehensive review of the literature published until mid-2016) as well as in other outstanding journals.

Considering the rapid growth of publications on this topic in recent years, we cordially invite you to contribute an original article/perspective/review focusing on one aspect of C–H activation and functionalization chemistry using both heterogeneous and homogeneous catalysis, including enzyme catalysis.

Prof. Immacolata Tommasi
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2200 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • C–H activation
  • C–C, C–O, C–N bond formation
  • Organometallic synthesis and catalysis
  • Heterogeneous catalysis
  • Enzyme catalysis
  • Reaction mechanisms
  • DFT studies

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Published Papers (5 papers)

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Research

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18 pages, 3029 KiB  
Article
C–H Bond Activation of Silyl-Substituted Pyridines with Bis(Phenolate)Yttrium Catalysts as a Facile Tool towards Hydroxyl-Terminated Michael-Type Polymers
by Thomas M. Pehl, Moritz Kränzlein, Friederike Adams, Andreas Schaffer and Bernhard Rieger
Catalysts 2020, 10(4), 448; https://doi.org/10.3390/catal10040448 - 22 Apr 2020
Cited by 7 | Viewed by 3779
Abstract
Herein, silicon-protected, ortho-methylated hydroxy-pyridines were reported as initiators in 2-aminoalkoxy-bis(phenolate)yttrium complexes for rare earth metal-mediated group-transfer polymerization (REM-GTP) of Michael-type monomers. To introduce these initiators, C−H bond activation was performed by reacting [(ONOO)tBuY(X)(thf)] (X = CH2TMS, thf [...] Read more.
Herein, silicon-protected, ortho-methylated hydroxy-pyridines were reported as initiators in 2-aminoalkoxy-bis(phenolate)yttrium complexes for rare earth metal-mediated group-transfer polymerization (REM-GTP) of Michael-type monomers. To introduce these initiators, C−H bond activation was performed by reacting [(ONOO)tBuY(X)(thf)] (X = CH2TMS, thf = tetrahydrofuran) with tert-butyl-dimethyl-silyl-functionalized α-methylpyridine to obtain the complex [(ONOOtBuY(X)(thf)] (X = 4-(4′-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-2,6-di-methylpyridine). These initiators served as functional end-groups in polymers produced via REM-GTP. In this contribution, homopolymers of 2-vinylpyridine (2VP) and diethyl vinyl phosphonate (DEVP) were produced. Activity studies and end-group analysis via mass spectrometry, size-exclusion chromatography (SEC) and NMR spectroscopy were performed to reveal the initiator efficiency, the catalyst activity towards both monomers as well as the initiation mechanism of this initiator in contrast to commonly used alkyl initiators. In addition, 2D NMR studies were used to further confirm the end-group integrity of the polymers. For all polymers, different deprotection routes were evaluated to obtain hydroxyl-terminated poly(2-vinylpyridine) (P2VP) and poly(diethyl vinyl phosphonate) (PDEVP). Such hydroxyl groups bear the potential to act as anchoring points for small bioactive molecules, for post-polymerization functionalization or as macroinitiators for further polymerizations. Full article
(This article belongs to the Special Issue Catalysts for C–H Activation and Functionalisation)
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14 pages, 2199 KiB  
Article
Conformationally Driven Ru(II)-Catalyzed Multiple ortho-C–H Bond Activation in Diphenylpyrazine Derivatives in Water: Where Is the Limit?
by Sara Hrovat, Miha Drev, Uroš Grošelj, Franc Perdih, Jurij Svete, Bogdan Štefane and Franc Požgan
Catalysts 2020, 10(4), 421; https://doi.org/10.3390/catal10040421 - 12 Apr 2020
Cited by 3 | Viewed by 2404
Abstract
Ru(II)/carboxylate/PPh3 catalyst system enabled the preparation of highly conjugated pyrazine derivatives in water under microwave irradiation. Both nitrogen atoms efficiently dictated cleavage of the ortho-C–H bonds in both benzene rings of 2,3-diphenylpyrazine substrates through chelation assistance. In conformationally more flexible diphenyldihydropyrazine [...] Read more.
Ru(II)/carboxylate/PPh3 catalyst system enabled the preparation of highly conjugated pyrazine derivatives in water under microwave irradiation. Both nitrogen atoms efficiently dictated cleavage of the ortho-C–H bonds in both benzene rings of 2,3-diphenylpyrazine substrates through chelation assistance. In conformationally more flexible diphenyldihydropyrazine 1, the arylation of four ortho-C–H bonds was possible, while in the aromatic analog 2, the triarylation was the limit. Full article
(This article belongs to the Special Issue Catalysts for C–H Activation and Functionalisation)
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14 pages, 5782 KiB  
Article
Effect of Fe and Mn Substitution in LaNiO3 on Exsolution, Activity, and Stability for Methane Dry Reforming
by Eswaravara Prasadarao Komarala, Ilia Komissarov and Brian A. Rosen
Catalysts 2020, 10(1), 27; https://doi.org/10.3390/catal10010027 - 25 Dec 2019
Cited by 34 | Viewed by 5281
Abstract
Perovskites LaNi0.8Fe0.2O3 and LaNi0.8Mn0.2O3 were synthesized using the co-precipitation method by substituting 20 mol.% of the Ni-site with Fe and Mn, respectively. Temperature programmed reduction (TPR) showed that the exsolution process in the [...] Read more.
Perovskites LaNi0.8Fe0.2O3 and LaNi0.8Mn0.2O3 were synthesized using the co-precipitation method by substituting 20 mol.% of the Ni-site with Fe and Mn, respectively. Temperature programmed reduction (TPR) showed that the exsolution process in the Fe- and Mn-substituted perovskites followed a two-step and three-step reduction pathway, respectively. Once exsolved, the catalysts were found to be able to regenerate the original perovskite when exposed to an oxygen environment but with different crystallographic properties. The catalytic activity for both materials after exsolution was measured for the methane dry reforming (DRM) reaction at 650 °C and 800 °C. Catalyst resistance against nickel agglomeration, unwanted phase changes, and carbon accumulation during DRM were analyzed using X-ray diffraction (XRD), transmission electron microscopy (TEM), and thermogravimetric analysis (TGA). The presence Fe alloying in the catalyst particles after exsolution from LaNi0.8Fe0.2O3 led to a lower methane conversion compared to the catalyst derived from LaNi0.8Mn0.2O3 where no alloying occurred. Full article
(This article belongs to the Special Issue Catalysts for C–H Activation and Functionalisation)
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Review

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20 pages, 5063 KiB  
Review
Recent Advances in Flavin-Dependent Halogenase Biocatalysis: Sourcing, Engineering, and Application
by Johannes Büchler, Athena Papadopoulou and Rebecca Buller
Catalysts 2019, 9(12), 1030; https://doi.org/10.3390/catal9121030 - 5 Dec 2019
Cited by 30 | Viewed by 8428
Abstract
The introduction of a halogen atom into a small molecule can effectively modulate its properties, yielding bioactive substances of agrochemical and pharmaceutical interest. Consequently, the development of selective halogenation strategies is of high technological value. Besides chemical methodologies, enzymatic halogenations have received increased [...] Read more.
The introduction of a halogen atom into a small molecule can effectively modulate its properties, yielding bioactive substances of agrochemical and pharmaceutical interest. Consequently, the development of selective halogenation strategies is of high technological value. Besides chemical methodologies, enzymatic halogenations have received increased interest as they allow the selective installation of halogen atoms in molecular scaffolds of varying complexity under mild reaction conditions. Today, a comprehensive library of aromatic halogenases exists, and enzyme as well as reaction engineering approaches are being explored to broaden this enzyme family’s biocatalytic application range. In this review, we highlight recent developments in the sourcing, engineering, and application of flavin-dependent halogenases with a special focus on chemoenzymatic and coupled biosynthetic approaches. Full article
(This article belongs to the Special Issue Catalysts for C–H Activation and Functionalisation)
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29 pages, 9391 KiB  
Review
Rh(III)-Catalyzed C–H Bond Activation for the Construction of Heterocycles with sp3-Carbon Centers
by Run Wang, Xiong Xie, Hong Liu and Yu Zhou
Catalysts 2019, 9(10), 823; https://doi.org/10.3390/catal9100823 - 30 Sep 2019
Cited by 29 | Viewed by 5628
Abstract
Rh(III)-catalyzed C–H activation features mild reaction conditions, good functional group tolerance, high reaction efficiency, and regioselectivity. Recently, it has attracted tremendous attention and has been employed to synthesize various heterocycles, such as indoles, isoquinolines, isoquinolones, pyrroles, pyridines, and polyheterocycles, which are important privileged [...] Read more.
Rh(III)-catalyzed C–H activation features mild reaction conditions, good functional group tolerance, high reaction efficiency, and regioselectivity. Recently, it has attracted tremendous attention and has been employed to synthesize various heterocycles, such as indoles, isoquinolines, isoquinolones, pyrroles, pyridines, and polyheterocycles, which are important privileged structures in biological molecules, natural products, and agrochemicals. In this short review, we attempt to present an overview of recent advances in Rh(III)-mediated C–H bond activation to generate diverse heterocyclic scaffolds with sp3 carbon centers. Full article
(This article belongs to the Special Issue Catalysts for C–H Activation and Functionalisation)
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