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Transition-Metal Catalysts for C–H Bond Functionalization of Heteroarenes
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Transition-Metal Catalysts for C–H Bond Functionalization of Heteroarenes

A special issue of Catalysts (ISSN 2073-4344).

Deadline for manuscript submissions: closed (10 October 2021) | Viewed by 27280

Special Issue Editor

Dr. Corinne Fruit

E-Mail Website
Guest Editor
Normandie University, UNIROUEN, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France
Interests: heteroarenes; organometallic chemistry; C–H activation; catalysis; kinases inhibitors; Alzheimer’s disease; antitumoral activities

Special Issue Information

Dear Colleagues,

C–C and C–X bond formation from direct C–H activation is now recognized as a powerful and straightforward strategy for the synthesis of complex molecules, and especially for late-stage functionalization. Many of these reactions allow a streamlined route to new functionalized heterocycle compounds. This Special Issue focuses on the site-selective C–H functionalization of heteroarenes for the formation of new bonds such as carbon–carbon and carbon–heteroatom (nitrogen, oxygen, sulfur, boron, fluorine, etc.). The late-stage functionalization applied to the synthesis of arrays of potential bioactive compounds is of great interest, as well as the synthesis of new organic materials. Communications, articles, and reviews dedicated to recent advances in this area are welcome. In addition, the enhancement of the reactions based on advances in technologies such as microwave and flow systems will be included.

Dr. Corinne Fruit
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 2700 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

  • Metal catalysis
  • C–H activation
  • C–C bond formation
  • C–X bond formation
  • Heteroaromatic
  • Site-selectivity
  • Late-stage functionalization
  • Microwave irradiation
  • Environmental catalysis
  • Organic material

Published Papers (7 papers)

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Research

Jump to: Review

19 pages, 2053 KiB  
Article
Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes
by Marco Lessi, Attilio Nania, Melania Pittari, Laura Lodone, Angela Cuzzola and Fabio Bellina
Catalysts 2021, 11(7), 762; https://0-doi-org.brum.beds.ac.uk/10.3390/catal11070762 - 23 Jun 2021
Cited by 2 | Viewed by 1944
Abstract
The construction of carbon–carbon bonds by direct involvement of two unactivated carbon–hydrogen bonds, without any directing group, ensures a high atom economy of the entire process. Here, we describe a simple protocol for the Pd(II)/Cu(II)-promoted intermolecular cross-dehydrogenative coupling (CDC) of 5-arylimidazoles, benzimidazoles, benzoxazole [...] Read more.
The construction of carbon–carbon bonds by direct involvement of two unactivated carbon–hydrogen bonds, without any directing group, ensures a high atom economy of the entire process. Here, we describe a simple protocol for the Pd(II)/Cu(II)-promoted intermolecular cross-dehydrogenative coupling (CDC) of 5-arylimidazoles, benzimidazoles, benzoxazole and 4,5-diphenylimidazole at their C-2 position with functionalized styrenes. This specific CDC, known as the Fujiwara–Moritani reaction or oxidative Heck coupling, also allowed the C-4 alkenylation of the imidazole nucleus when both 2 and 5 positions were occupied. Full article
(This article belongs to the Special Issue Transition-Metal Catalysts for C–H Bond Functionalization of Heteroarenes)
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13 pages, 1765 KiB  
Article
Copper-Catalyzed C–H Arylation of Fused-Pyrimidinone Derivatives Using Diaryliodonium Salts
by Alexandra Pacheco-Benichou, Eugénie Ivendengani, Ioannis K. Kostakis, Thierry Besson and Corinne Fruit
Catalysts 2021, 11(1), 28; https://0-doi-org.brum.beds.ac.uk/10.3390/catal11010028 - 29 Dec 2020
Cited by 6 | Viewed by 2303
Abstract
Copper-catalyzed Csp2–Csp2 bond forming reactions through C–H activation are still one of the most useful strategies for the diversification of heterocyclic moieties using various coupling partners. A catalytic protocol for the C–H (hetero)arylation of thiazolo[5,4-f]quinazolin-9(8H)-ones and more generally fused-pyrimidinones [...] Read more.
Copper-catalyzed Csp2–Csp2 bond forming reactions through C–H activation are still one of the most useful strategies for the diversification of heterocyclic moieties using various coupling partners. A catalytic protocol for the C–H (hetero)arylation of thiazolo[5,4-f]quinazolin-9(8H)-ones and more generally fused-pyrimidinones using catalyst loading of CuI with diaryliodonium triflates as aryl source under microwave irradiation has been disclosed. The selectivity of the transfer of the aryl group was also disclosed in the case of unsymmetrical diaryliodonium salts. Specific phenylation of valuable fused-pyrimidinones including quinazolinone are provided. This strategy enables a rapid access to an array of various (hetero)arylated N-containing polyheteroaromatics as new potential bioactive compounds. Full article
(This article belongs to the Special Issue Transition-Metal Catalysts for C–H Bond Functionalization of Heteroarenes)
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23 pages, 7882 KiB  
Article
Syntheses of 3,3-Disubstituted Dihydrobenzofurans, Indolines, Indolinones and Isochromanes by Palladium-Catalyzed Tandem Reaction Using Pd(PPh3)2Cl2/(±)-BINAP as a Catalytic System
by Guizhou Yue, Sicheng Li, Dan Jiang, Gang Ding, Juhua Feng, Huabao Chen, Chunping Yang, Zhongqiong Yin, Xu Song, Xiaoxia Liang, Li Zhang, Xianxiang Wang and Cuifen Lu
Catalysts 2020, 10(9), 1084; https://0-doi-org.brum.beds.ac.uk/10.3390/catal10091084 - 18 Sep 2020
Cited by 3 | Viewed by 2596
Abstract
A general procedure for the tandem arylation reaction of arylbromide with heteroaryl compounds was developed by using Pd(PPh3)2Cl2/(±)-BINAP (1,1′-Binaphthalene-2,2′-diylbis (diphenylphosphane)) as catalytic system. Both sulphur- and oxygen-containing heterocycles were also employed as an efficient reagent for arylation, [...] Read more.
A general procedure for the tandem arylation reaction of arylbromide with heteroaryl compounds was developed by using Pd(PPh3)2Cl2/(±)-BINAP (1,1′-Binaphthalene-2,2′-diylbis (diphenylphosphane)) as catalytic system. Both sulphur- and oxygen-containing heterocycles were also employed as an efficient reagent for arylation, which gave moderate to excellent yields with moderate to good regioselectivities (5:1 to > 20:1 ir (isomer ratio)). Except for dihydrobenzofurans, indolines and indolinones, this type of tandem reaction was also expanded to synthesize isochromanes. The synthesized new compounds were well characterized through different spectroscopic techniques, such as 1H and 13C NMR (nuclear magnetic resonance), and mass spectral analysis. Full article
(This article belongs to the Special Issue Transition-Metal Catalysts for C–H Bond Functionalization of Heteroarenes)
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10 pages, 1569 KiB  
Article
Eosin Y-Catalyzed Visible-Light-Mediated Aerobic Transformation of Pyrazolidine-3-One Derivatives
by Nejc Petek, Uroš Grošelj, Jurij Svete, Franc Požgan, Drago Kočar and Bogdan Štefane
Catalysts 2020, 10(9), 981; https://0-doi-org.brum.beds.ac.uk/10.3390/catal10090981 - 01 Sep 2020
Cited by 5 | Viewed by 3083
Abstract
By utilizing an underexplored reactivity of N1-substituted pyrazolidine-3-ones, we developed a visible-light-induced aerobic oxidation of N1-substituted pyrazolidine-3-one derivatives yielding the corresponding azomethine imines. The resulting azomethine imines can be further reacted with ynones in situ under copper catalyzed [3 + 2] cycloaddition reaction [...] Read more.
By utilizing an underexplored reactivity of N1-substituted pyrazolidine-3-ones, we developed a visible-light-induced aerobic oxidation of N1-substituted pyrazolidine-3-one derivatives yielding the corresponding azomethine imines. The resulting azomethine imines can be further reacted with ynones in situ under copper catalyzed [3 + 2] cycloaddition reaction conditions yielding the corresponding pyrazolo[1,2-a]pyrazoles in good yields. The methodology can be extended to other 1-aryl-substituted pyrazolidinones which undergo endocyclic oxidation deriving the corresponding pyrazolones as single products. Full article
(This article belongs to the Special Issue Transition-Metal Catalysts for C–H Bond Functionalization of Heteroarenes)
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23 pages, 5079 KiB  
Article
Radical C–H 18F-Difluoromethylation of Heteroarenes with [18F]Difluoromethyl Heteroaryl-Sulfones by Visible Light Photoredox Catalysis
by Agostinho Luís Pereira Lemos, Laura Trump, Bénédicte Lallemand, Patrick Pasau, Joël Mercier, Christian Lemaire, Jean-Christophe Monbaliu, Christophe Genicot and André Luxen
Catalysts 2020, 10(3), 275; https://0-doi-org.brum.beds.ac.uk/10.3390/catal10030275 - 01 Mar 2020
Cited by 9 | Viewed by 5146
Abstract
The 18F-labeling of CF2H groups has been recently studied in radiopharmaceutical chemistry owing to the favorable nuclear and physical characteristics of the radioisotope 18F for positron emission tomography (PET). Following up on the reported efficiency of the [18 [...] Read more.
The 18F-labeling of CF2H groups has been recently studied in radiopharmaceutical chemistry owing to the favorable nuclear and physical characteristics of the radioisotope 18F for positron emission tomography (PET). Following up on the reported efficiency of the [18F]difluoromethyl benzothiazolyl-sulfone ([18F]1) as a 18F-difluoromethylating reagent, we investigated the influence of structurally-related [18F]difluoromethyl heteroaryl-sulfones in the reactivity toward the photoredox C–H 18F-difluoromethylation of heteroarenes under continuous-flow conditions. In the present work, six new [18F]difluoromethyl heteroaryl-sulfones [18F]5a–[18F]5f were prepared and, based on the overall radiochemical yields (RCYs), three of these reagents ([18F]5a, [18F]5c, and [18F]5f) were selected for the fully automated radiosynthesis on a FASTlabTM synthesizer (GE Healthcare) at high level of starting radioactivity. Subsequently, their efficiency as 18F-difluoromethylating reagents was evaluated using the antiherpetic drug acyclovir as a model substrate. Our results showed that the introduction of molecular modifications in the structure of [18F]1 influenced the amount of fac-IrIII(ppy)3 and the residence time needed to ensure a complete C–H 18F-difluoromethylation process. The photocatalytic C–H 18F-difluoromethylation reaction with the reagents [18F]5a, [18F]5c, and [18F]5f was extended to other heteroarenes. Radical-trapping experiments demonstrated the likely involvement of radical species in the C–H 18F-difluoromethylation process. Full article
(This article belongs to the Special Issue Transition-Metal Catalysts for C–H Bond Functionalization of Heteroarenes)
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Review

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48 pages, 25283 KiB  
Review
Pd-Catalyzed Intermolecular Dehydrogenative Heck Reactions of Five-Membered Heteroarenes
by Jean Le Bras and Jacques Muzart
Catalysts 2020, 10(5), 571; https://0-doi-org.brum.beds.ac.uk/10.3390/catal10050571 - 19 May 2020
Cited by 22 | Viewed by 4351
Abstract
The Pd-mediated cross-coupling of (hetero)arenes with alkenes may be an effective method for the formation of a C–C bond from two C–H bonds. Discovered by Fujiwara and co-workers in 1967, this reaction led to a number of reports that we firstly highlighted in [...] Read more.
The Pd-mediated cross-coupling of (hetero)arenes with alkenes may be an effective method for the formation of a C–C bond from two C–H bonds. Discovered by Fujiwara and co-workers in 1967, this reaction led to a number of reports that we firstly highlighted in 2011 (review with references till June 2010) and for which, we retained the name “dehydrogenative Heck reaction”. The topic, especially the reactions of five-membered heteroarenes, has been the subject of intensive research over the last ten years. The present review is limited to these dehydrogenative Heck reactions published since 2010, underlining the progress of the procedures. Full article
(This article belongs to the Special Issue Transition-Metal Catalysts for C–H Bond Functionalization of Heteroarenes)
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34 pages, 7992 KiB  
Review
Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes
by Alexandra Pacheco-Benichou, Thierry Besson and Corinne Fruit
Catalysts 2020, 10(5), 483; https://0-doi-org.brum.beds.ac.uk/10.3390/catal10050483 - 28 Apr 2020
Cited by 27 | Viewed by 6846
Abstract
Owing to the pioneering works performed on the metal-catalyzed sp2 C–H arylation of indole and pyrrole by Sanford and Gaunt, N– and C-arylation involving diaryliodonium salts offers an attractive complementary strategy for the late-stage diversification of heteroarenes. The main feature of [...] Read more.
Owing to the pioneering works performed on the metal-catalyzed sp2 C–H arylation of indole and pyrrole by Sanford and Gaunt, N– and C-arylation involving diaryliodonium salts offers an attractive complementary strategy for the late-stage diversification of heteroarenes. The main feature of this expanding methodology is the selective incorporation of structural diversity into complex molecules which usually have several C–H bonds and/or N–H bonds with high tolerance to functional groups and under mild conditions. This review summarizes the main recent achievements reported in transition-metal-catalyzed N– and/or C–H arylation of heteroarenes using acyclic diaryliodonium salts as coupling partners. Full article
(This article belongs to the Special Issue Transition-Metal Catalysts for C–H Bond Functionalization of Heteroarenes)
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