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Catalytic Organic Synthesis—a Special Issue in Honor of Professor Masahiro...
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Catalytic Organic Synthesis—a Special Issue in Honor of Professor Masahiro Miura

A special issue of Chemistry (ISSN 2624-8549). This special issue belongs to the section "Molecular Organics".

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 9892

Special Issue Editors

Prof. Dr. Tetsuya Satoh

E-Mail Website
Guest Editor
Department of Chemistry, Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan
Interests: organic synthesis; transition metal catalyst; C–H functionalization; cross-coupling
Prof. Dr. Koji Hirano

E-Mail Website
Guest Editor
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka, Japan
Interests: organic synthesis; organometallic chemistry; catalysis; asymmetric synthesis; heteroatoms

Special Issue Information

Dear Colleagues,

This Special Issue of Chemistry is dedicated to Professor Masahiro Miura for his outstanding contribution to catalytic organic synthesis. After obtaining a Ph.D. degree at Osaka University, Japan, in 1983, he started his academic career as assistant professor at the Faculty of Engineering, Osaka University, in 1984, and was promoted to associate professor in 1994 and full professor in 2005. He also worked as a Humboldt postdoctoral fellow at Karlsruhe University, Germany, in 1990–1991. He moved to ICS-OTRI, Osaka University, as a specially appointed professor in 2021. He has made significant contributions to the areas of catalytic chemistry and π-conjugated molecule synthesis, and is one of the renowned pioneers of direct coupling reactions via C-H bond cleavage, which are currently recognized to be highly important in realizing atom- and step-economic synthesis in environmentally benign manners.

All contributions related to the activity of Prof. Miura including catalysis, organometallics, and π-conjugated molecule synthesis are warmly welcomed.

Prof. Dr. Tetsuya Satoh
Prof. Dr. Koji Hirano
Guest Editors

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. Chemistry is an international peer-reviewed open access semimonthly 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 1800 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

  • homogeneous catalysis
  • C–H bond cleavage
  • C–C bond cleavage
  • C–C bond formation
  • direct coupling
  • annulation
  • cyclization
  • fused aromatic compound
  • carbo- and heterocycle synthesis

Published Papers (7 papers)

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Research

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18 pages, 4777 KiB  
Article
Iron-Promoted 1,5-Substitution Reaction of Endocyclic Enyne Oxiranes with MeMgBr: A Stereoselective Method for the Synthesis of Exocyclic 2,4,5-Trienol Derivatives
by Melih Kuş, Cenk Omur, Sıla Karaca and Levent Artok
Chemistry 2023, 5(4), 2682-2699; https://doi.org/10.3390/chemistry5040173 - 01 Dec 2023
Viewed by 775
Abstract
The iron-promoted 1,5-substitution reaction of endocyclic oxiranes with MeMgBr yields exocyclic 2,4,5-trienols with high diastereomeric ratios of up to 100:0. However, for the method’s success, the oxirane ring must have a trans-configuration. The reactions exhibit strong stereoselectivity concerning the methylation mode and [...] Read more.
The iron-promoted 1,5-substitution reaction of endocyclic oxiranes with MeMgBr yields exocyclic 2,4,5-trienols with high diastereomeric ratios of up to 100:0. However, for the method’s success, the oxirane ring must have a trans-configuration. The reactions exhibit strong stereoselectivity concerning the methylation mode and the configuration of the resulting exocyclic double bond. Enantiomerically pure enyne oxiranes can be synthesized through Sharpless asymmetric dihydroxylation and subsequent manipulations. With these reagents, it has been possible to produce exocyclic 2,4,5-trienols in enantiopure forms. Importantly, this process maintains chirality without degradation during the center-to-axis transfer of chirality. Full article
(This article belongs to the Special Issue Catalytic Organic Synthesis—a Special Issue in Honor of Professor Masahiro Miura)
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11 pages, 1623 KiB  
Communication
Efficient Metal-Free Oxidative C–H Amination for Accessing Dibenzoxazepinones via μ-Oxo Hypervalent Iodine Catalysis
by Hirotaka Sasa, Syotaro Hamatani, Mayu Hirashima, Naoko Takenaga, Tomonori Hanasaki and Toshifumi Dohi
Chemistry 2023, 5(4), 2155-2165; https://doi.org/10.3390/chemistry5040145 - 12 Oct 2023
Viewed by 1025
Abstract
Dibenzoxazepinones exhibit unique biological activities and serve as building blocks for synthesizing pharmaceutical compounds. Despite remarkable advancements in organic chemistry and recent developments in synthetic approaches to dibenzoxazepinone motifs, there is a strong demand for more streamlined synthesis methods. The application of the [...] Read more.
Dibenzoxazepinones exhibit unique biological activities and serve as building blocks for synthesizing pharmaceutical compounds. Despite remarkable advancements in organic chemistry and recent developments in synthetic approaches to dibenzoxazepinone motifs, there is a strong demand for more streamlined synthesis methods. The application of the catalytic C–H amination strategy, which enables the direct transformation of inert aromatic C–H bonds into C–N bonds, offers a rapid route to access dibenzoxazepinone frameworks. Hypervalent-iodine-catalyzed oxidative C–H amination has the potential to become an effective approach for synthesizing dibenzoxazepinones. In this study, we present our method of employing μ-oxo hypervalent iodine catalysis for intramolecular oxidative C–H amination of O-aryl salicylamides, facilitating the synthesis of target dibenzoxazepinone derivatives bearing various functional groups in a highly efficient manner. Full article
(This article belongs to the Special Issue Catalytic Organic Synthesis—a Special Issue in Honor of Professor Masahiro Miura)
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7 pages, 949 KiB  
Communication
Isoselenazole Synthesis by Rh-Catalyzed Direct Annulation of Benzimidates with Sodium Selenite
by Qing-Feng Xu-Xu, Yuji Nishii and Masahiro Miura
Chemistry 2023, 5(4), 2068-2074; https://doi.org/10.3390/chemistry5040140 - 23 Sep 2023
Viewed by 813
Abstract
Organoselenium compounds have attracted significant research interest because of their potent therapeutic activities and indispensable applications in the organic chemistry field. The selenation reactions conventionally rely on the use of sensitive Se reagents; thus, new synthetic methods with improved efficiency and operational simplicity [...] Read more.
Organoselenium compounds have attracted significant research interest because of their potent therapeutic activities and indispensable applications in the organic chemistry field. The selenation reactions conventionally rely on the use of sensitive Se reagents; thus, new synthetic methods with improved efficiency and operational simplicity have recently been of particular interest. In this manuscript, we report a Rh-catalyzed direct selenium annulation using tractable sodium selenite (Na2SeO3) as the limiting reagent. The selenite species was converted to highly electrophilic SeO(OBz)2 in situ upon treatment with Bz2O, thereby undergoing C–H/N–H double nucleophilic selenation. A series of benzimidates successfully underwent selenation under mild reaction conditions to afford isoselenazole derivatives. Full article
(This article belongs to the Special Issue Catalytic Organic Synthesis—a Special Issue in Honor of Professor Masahiro Miura)
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12 pages, 2938 KiB  
Article
Direct Aniline Formation with Benzene and Hydroxylamine
by Ningyu Liu, Matthew D. Sleck and William D. Jones
Chemistry 2023, 5(4), 2056-2067; https://doi.org/10.3390/chemistry5040139 - 23 Sep 2023
Viewed by 2181
Abstract
A single-step method for aniline formation was examined. Using a vanadate catalyst with an iron oxide co-catalyst and hydroxylamine hydrochloride as the amine source, an up to 90% yield of aniline was obtained with high selectivity. Further study showed that the overall reaction [...] Read more.
A single-step method for aniline formation was examined. Using a vanadate catalyst with an iron oxide co-catalyst and hydroxylamine hydrochloride as the amine source, an up to 90% yield of aniline was obtained with high selectivity. Further study showed that the overall reaction was pseudo-second order in terms of hydroxylamine concentration. Regioselective H-D exchange experiments suggest that the C-N bond formation step occurs via an irreversible electrophilic pathway. Based on all of the key observations, a mechanism is proposed. Full article
(This article belongs to the Special Issue Catalytic Organic Synthesis—a Special Issue in Honor of Professor Masahiro Miura)
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9 pages, 2057 KiB  
Communication
Palladium-Catalyzed sp3 C–H Acetoxylation of α,α-Disubstituted α-Amino Acids
by Atsushi Matsumura, Yoshinosuke Usuki and Tetsuya Satoh
Chemistry 2023, 5(2), 1369-1377; https://doi.org/10.3390/chemistry5020093 - 01 Jun 2023
Viewed by 1324
Abstract
The sp3 C–H acetoxylation at the β-position of α,α-disubstituted α-amino acids proceeds smoothly under palladium catalysis in the presence of PhI(OAc)2. This reaction provides a straightforward synthetic route to non-natural β-acetoxy-α-amino acids. The reaction of α-aminocyclopropanecarboxylic acid takes place via [...] Read more.
The sp3 C–H acetoxylation at the β-position of α,α-disubstituted α-amino acids proceeds smoothly under palladium catalysis in the presence of PhI(OAc)2. This reaction provides a straightforward synthetic route to non-natural β-acetoxy-α-amino acids. The reaction of α-aminocyclopropanecarboxylic acid takes place via ring-opening to selectively afford an acyclic γ-acetoxy-α,β-unsaturated amino acid. Full article
(This article belongs to the Special Issue Catalytic Organic Synthesis—a Special Issue in Honor of Professor Masahiro Miura)
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15 pages, 8143 KiB  
Article
Investigation of the Properties of Mo/ZSM-5 Catalysts Based on Zeolites with Microporous and Micro–Mesoporous Structures
by Andrey A. Stepanov, Ludmila L. Korobitsyna and Alexander V. Vosmerikov
Chemistry 2023, 5(2), 1256-1270; https://doi.org/10.3390/chemistry5020085 - 17 May 2023
Cited by 1 | Viewed by 1399
Abstract
The dehydroaromatization of methane (MDA) is of great interest as a promising process for processing natural and associated petroleum gases, the main component of which is methane. The rapid loss of catalyst activity because of coke formation hinders the introduction of the DHA [...] Read more.
The dehydroaromatization of methane (MDA) is of great interest as a promising process for processing natural and associated petroleum gases, the main component of which is methane. The rapid loss of catalyst activity because of coke formation hinders the introduction of the DHA methane process into the industry. Therefore, the aim of this research was to find ways to improve Mo/ZSM-5 catalysts for MDA. The paper presents the results of the synthesis of high-silica zeolites of the ZSM-5 type with microporous and micro–mesoporous structures, the preparation of Mo/ZSM-5 catalysts based on them, and the study of the physicochemical and catalytic properties of the obtained samples during the non-oxidative conversion of methane into aromatic hydrocarbons. Zeolite catalysts were investigated using IR spectroscopy, X-ray diffraction, TPD-NH3, SEM, HR-TEM, and N2 adsorption. It was found that the addition of carbon black in the stage of the synthesis of zeolite type ZSM-5 did not lead to structural changes, and the obtained samples had a crystallinity degree equal to 100%. The creation of the micro–mesoporous structure in Mo/ZSM-5 catalysts led to an increase in their activity and stability in the process of methane dehydroaromatization. The highest conversion of methane was observed on a 4.0%Mo/ZSM-5 catalyst prepared based on zeolite synthesized using 1.0% carbon black and was 13.0% after 20 min of reaction, while the benzene yield reached 7.0%. It was shown using HR-TEM that a more uniform distribution of the active metal component was observed in a zeolite catalyst with a micro–mesoporous structure than in a microporous zeolite. Full article
(This article belongs to the Special Issue Catalytic Organic Synthesis—a Special Issue in Honor of Professor Masahiro Miura)
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Review

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43 pages, 7300 KiB  
Review
Recent Advances in C–H Functionalization of Pyrenes
by Srinivasarao Arulananda Babu, Arup Dalal and Subhankar Bodak
Chemistry 2023, 5(4), 2713-2755; https://doi.org/10.3390/chemistry5040175 - 11 Dec 2023
Cited by 1 | Viewed by 1137
Abstract
In recent years, transition metal-catalyzed C–H activation and site-selective functionalization have been considered to be valuable synthetic tactics to functionalize organic compounds containing multiple C–H bonds. Pyrene is one of the privileged and notorious polycyclic aromatic hydrocarbons. Pyrene and its derivatives have found [...] Read more.
In recent years, transition metal-catalyzed C–H activation and site-selective functionalization have been considered to be valuable synthetic tactics to functionalize organic compounds containing multiple C–H bonds. Pyrene is one of the privileged and notorious polycyclic aromatic hydrocarbons. Pyrene and its derivatives have found applications in various branches of chemical sciences, including organic chemistry, chemical biology, supramolecular sciences, and material sciences. Given the importance of pyrene derivatives, several classical methods, including the C–H functionalization method, have been developed for synthesizing modified pyrene scaffolds. This review attempts to cover the recent developments in the area pertaining to the modification of the pyrene motif through the C–H activation process and the functionalization of C–H bonds present in the pyrene motif, leading to functionalized pyrenes. Full article
(This article belongs to the Special Issue Catalytic Organic Synthesis—a Special Issue in Honor of Professor Masahiro Miura)
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