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Recent Advances in C-H Functionalization
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Recent Advances in C-H Functionalization

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 August 2020) | Viewed by 17834

Special Issue Editor

Dr. Patricia Garcia-Garcia

E-Mail Website
Guest Editor
Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química “Andrés M. del Río” (IQAR), Universidad de Alcalá, 28805 Alcalá de Henares, Spain
Interests: organic synthesis; homogeneous catalysis; BN-arenes; alkyne activation; C-H functionalization

Special Issue Information

Dear Colleagues,

C-H functionalization has become, in the last decades, an extremely powerful tool for organic synthesis. The direct conversion of a C-H bond to other functionalities is highly attractive as it removes the need for pre-functionalization steps and, therefore, streamlines synthetic strategies. That said, the ubiquity of C-H bonds makes site selectivity an important issue to address in these transformations. There are two main strategies that have been employed to achieve regioselective C-H functionalization. In some cases, mainly for heterocyclic compounds, the inherent electronic and steric properties of the substrate determine the possibility of successfully achieving regioselective C-H functionalization. Otherwise, the efficiency of the reactions usually relies on the presence of directing groups, and metal-catalysis has played a fundamental role in the advancement of these methodologies. Nowadays, a wide number of procedures for the predictable regioselective introduction of functionality in C-H bonds are available, but significant improvements in this field are still to come. Some examples of the upcoming innovations include the development of more efficient methods and methods able to take place under milder conditions, the use of more readily available catalysts, and wider scopes that allow for complementary regioselectivities.

This Special Issue aims to cover recent advances in regioselective C-H functionalization, focusing on the two main strategies mentioned above and including reactions involving both aromatic compounds and alkanes, with the formation of either C-C or C-heteroatom bonds.

We invite research papers and reviews covering the above-mentioned topics.

Dr. Patricia Garcia-Garcia
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. Molecules 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 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

  • C-H bond
  • C-H functionalization
  • directing group
  • metal-catalysis
  • organic synthesis
  • regioselectivity

Published Papers (4 papers)

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Research

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14 pages, 2646 KiB  
Article
Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry
by Michael Oschmann, Linus Johansson Holm, Monireh Pourghasemi-Lati and Oscar Verho
Molecules 2020, 25(2), 361; https://doi.org/10.3390/molecules25020361 - 15 Jan 2020
Cited by 10 | Viewed by 4409
Abstract
Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C–H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C–H arylation reactions, Pd catalysis was used to install a [...] Read more.
Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C–H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C–H arylation reactions, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a one-pot, two-step transamidation procedure, which proceeded via the intermediate N-acyl-Boc-carbamates. Given the high efficiency and modularity of this synthetic strategy, it constitutes a very attractive method for generating structurally diverse collections of benzofuran derivatives for small molecule screening campaigns. Full article
(This article belongs to the Special Issue Recent Advances in C-H Functionalization)
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Review

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60 pages, 26195 KiB  
Review
Regioselective Functionalization of Quinolines through C-H Activation: A Comprehensive Review
by Alessandra Corio, Christine Gravier-Pelletier and Patricia Busca
Molecules 2021, 26(18), 5467; https://doi.org/10.3390/molecules26185467 - 8 Sep 2021
Cited by 20 | Viewed by 5511
Abstract
Quinoline is a versatile heterocycle that is part of numerous natural products and countless drugs. During the last decades, this scaffold also became widely used as ligand in organometallic catalysis. Therefore, access to functionalized quinolines is of great importance and continuous efforts have [...] Read more.
Quinoline is a versatile heterocycle that is part of numerous natural products and countless drugs. During the last decades, this scaffold also became widely used as ligand in organometallic catalysis. Therefore, access to functionalized quinolines is of great importance and continuous efforts have been made to develop efficient and regioselective synthetic methods. In this regard, C-H functionalization through transition metal catalysis, which is nowadays the Graal of organic green chemistry, represents the most attractive strategy. We aim herein at providing a comprehensive review of methods that allow site-selective metal-catalyzed C-H functionalization of quinolines, or their quinoline N-oxides counterparts, with a specific focus on their scope and limitations, as well as mechanistic aspects if that accounts for the selectivity. Full article
(This article belongs to the Special Issue Recent Advances in C-H Functionalization)
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58 pages, 12453 KiB  
Review
Rollover Cyclometalation as a Valuable Tool for Regioselective C–H Bond Activation and Functionalization
by Antonio Zucca and Maria I. Pilo
Molecules 2021, 26(2), 328; https://doi.org/10.3390/molecules26020328 - 10 Jan 2021
Cited by 19 | Viewed by 3131
Abstract
Rollover cyclometalation constitutes a particular case of cyclometallation reaction. This reaction occurs when a chelated heterocyclic ligand loses its bidentate coordination mode and undergoes an internal rotation, after which a remote C–H bond is regioselectively activated, affording an uncommon cyclometalated complex, called “rollover [...] Read more.
Rollover cyclometalation constitutes a particular case of cyclometallation reaction. This reaction occurs when a chelated heterocyclic ligand loses its bidentate coordination mode and undergoes an internal rotation, after which a remote C–H bond is regioselectively activated, affording an uncommon cyclometalated complex, called “rollover cyclometalated complex”. The key of the process is the internal rotation of the ligand, which occurs before the C–H bond activation and releases from coordination a donor atom. The new “rollover” ligand has peculiar properties, being a ligand with multiple personalities, no more a spectator in the reactivity of the complex. The main reason of this peculiarity is the presence of an uncoordinated donor atom (the one initially involved in the chelation), able to promote a series of reactions not available for classic cyclometalated complexes. The rollover reaction is highly regioselective, because the activated C–H bond is usually in a symmetric position with respect to the donor atom which detaches from the metal stating the rollover process. Due to this novel behavior, a series of potential applications have appeared in the literature, in fields such as catalysis, organic synthesis, and advanced materials. Full article
(This article belongs to the Special Issue Recent Advances in C-H Functionalization)
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34 pages, 14189 KiB  
Review
Recent Developments in Transition-Metal Catalyzed Direct C–H Alkenylation, Alkylation, and Alkynylation of Azoles
by Su Chen, Prabhat Ranjan, Leonid G. Voskressensky, Erik V. Van der Eycken and Upendra K. Sharma
Molecules 2020, 25(21), 4970; https://doi.org/10.3390/molecules25214970 - 27 Oct 2020
Cited by 27 | Viewed by 3688
Abstract
The transition metal-catalyzed C–H bond functionalization of azoles has emerged as one of the most important strategies to decorate these biologically important scaffolds. Despite significant progress in the C–H functionalization of various heteroarenes, the regioselective alkylation and alkenylation of azoles are still arduous [...] Read more.
The transition metal-catalyzed C–H bond functionalization of azoles has emerged as one of the most important strategies to decorate these biologically important scaffolds. Despite significant progress in the C–H functionalization of various heteroarenes, the regioselective alkylation and alkenylation of azoles are still arduous transformations in many cases. This review covers recent advances in the direct C–H alkenylation, alkylation and alkynylation of azoles utilizing transition metal-catalysis. Moreover, the limitations of different strategies, chemoselectivity and regioselectivity issues will be discussed in this review. Full article
(This article belongs to the Special Issue Recent Advances in C-H Functionalization)
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