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Catalyzed Mizoroki–Heck Reaction or C–H Activation II

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A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (31 May 2022) | Viewed by 10324

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Special Issue Editor

Prof. Dr. Sabine Berteina-Raboin

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Guest Editor

Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans, UMR-CNRS 7311, BP 6759, Rue de Chartres, 45067 Orléans, France
Interests: methodological studies in heterocyclic chemistry; formation of C–C, C–N, C–O, and C–S bonds; synthesis or hemisynthesis of heterocyclic or bioactive molecules or natural products; environmentally friendly methods
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Special Issue Information

Dear Colleagues,

This issue is a continuation of the previous successful Special Issue “Catalyzed Mizoroki–Heck Reaction or C–H activation”.

In the last few decades, research on the elaboration of palladium–catalytic processes of C–C bonds or C–H bond activation has grown considerably, but many improvements are still possible in terms of selectivity or even enantioselectivity via the development of new ligands or the study of the catalytic effect of other metals to carry out the same chemical transformations.

The attention paid to environmentally-friendly methods in terms of the quantities of catalysts, ligands, and solvents is currently indispensable. The Mizoroki–Heck reaction is one of these important catalytic methods to generate C–C bonds in organic synthesis and is also possible via C–H activation.

This Special Issue on “Catalyzed Mirozoki–Heck Reaction or C-H Activation” will focus on new advances in the formation of C–C bonds via the Mizoroki–Heck reaction or new C–H activation methods. In doing so, we place specific emphasis on original research papers and short reviews on the synthesis of biologically-active compounds using these catalytic processes, identification of new catalysts, synthesis of new ligands allowing selectivity or enantioselectivity of the synthetic processes, activity, and the stability of catalyst under turnover conditions and all improvements in catalytic processes for obtaining C–C bonds or C–H bond activation.

Prof. Dr. Sabine Berteina-Raboin
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.

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Keywords

Mizoroki–Heck reaction
C–H bond activation
Green and sustainable chemistry
Solvents and catalyst recyclability
New ligands for palladium–catalytic processes

Published Papers (4 papers)

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Research

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26 pages, 9427 KiB

Open AccessArticle

A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions

by Simon Garnier, Kévin Brugemann, Agnieszka Zak, Johnny Vercouillie, Marie Potier-Cartereau, Mathieu Marchivie, Sylvain Routier and Frédéric Buron

Catalysts 2022, 12(8), 828; https://doi.org/10.3390/catal12080828 - 27 Jul 2022

Cited by 1 | Viewed by 1601

Abstract

The first access to N-1, N-4 disubstituted pyrrolo[2,3-d][1,2,3]triazoles is reported. The series were generated using a “one-pot” MCR, leading to a single regioisomer of the attempted heteroaromatic skeleton in good yields. Next, the functionalization of C-5 and C-6 positions was investigated. (Het)aryl groups were introduced at the C-5 and C-6 positions of the pyrrolo[2,3-d][1,2,3]triazoles using regioselective electrophilic brominations followed by Suzuki–Miyaura cross coupling reactions. Palladium-catalyzed cross-coupling conditions were optimized and a representative library of various boronic acids was employed to establish the scope and limitations of the method. Full article

(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H Activation II)

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26 pages, 8090 KiB

Open AccessArticle

N-Directed Pd-Catalyzed Photoredox-Mediated C–H Arylation for Accessing Phenyl-Extended Analogues of Biginelli/Suzuki-Derived Ethyl 4-Methyl-2,6-diphenylpyrimidine-5-carboxylates

by Savvas N. Georgiades, Persefoni G. Nicolaou and Nikos Panagiotou

Catalysts 2021, 11(9), 1071; https://doi.org/10.3390/catal11091071 - 03 Sep 2021

Cited by 1 | Viewed by 2220

Abstract

The availability and application of direct, functional group-compatible C–H activation methods for late-stage modification of small-molecule bioactives and other valuable materials remains an ongoing challenge in organic synthesis. In the current study, we demonstrate that a LED-activated, photoredox-mediated, Pd(OAc)₂-catalyzed C–H arylation, employing a phenyldiazonium aryl source and either tris(2,2′-bipyridine)ruthenium(II) or (2,2′-bipyridine)bis[3,5-di-fluoro-2-[5-(trifluoromethyl)-2-pyridinyl-kN][phenyl-kC]iridium(III) as photoredox initiator, may successfully produce unprecedented mono- and bis-phenyl derivatives of functionality-rich 2,6-diphenylpyrimidine substrates at room temperature. The series of 19 substrates employed herein, which share the biologically-relevant 4-methyl-2,6-diphenylpyrimidine-5-carboxylate scaffold, were generated via a synthetic route involving (3-component) Biginelli condensation, oxidative dehydrogenation of the obtained 3,4-dihydropyrimidin-2(1H)-one to 2-hydroxypyrimidine, O-sulfonylation, and Suzuki-Miyaura C–C cross-coupling. Submission of these substrates to pyrimidine-N-atom-directed C–H arylation conditions led to regioselective phenylation at the ortho site(s) of the pyrimidine-C2-connected phenyl ring, revealing substituent-dependent electronic and steric effects. A focused library of 18 mono- and 10 bis-phenyl derivatives was generated. Its members exhibit interesting 3D and peripheral substitution features that render them promising for evaluation in drug discovery efforts. Full article

(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H Activation II)

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13 pages, 2652 KiB

Open AccessFeature PaperArticle

Eucalyptol: A Bio-Based Solvent for the Synthesis of O,S,N-Heterocycles. Application to Hiyama Coupling, Cyanation, and Multicomponent Reactions

by Joana F. Campos, Véronique Ferreira and Sabine Berteina-Raboin

Catalysts 2021, 11(2), 222; https://doi.org/10.3390/catal11020222 - 08 Feb 2021

Cited by 7 | Viewed by 2489

Abstract

We report here the use of eucalyptol as a bio-based solvent for Hiyama coupling, cyanation, and multicomponent reactions on O,S,N-heterocycles. These heterocycles were chosen as targets or as starting materials given their biological potential; they play an important role in therapeutically active compounds. Once again, eucalyptol proved to be a credible and sustainable alternative to common solvents. Full article

(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H Activation II)

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Review

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26 pages, 14648 KiB

Open AccessFeature PaperReview

Synthesis of Conjugated Dienes in Natural Compounds

by Geoffrey Dumonteil and Sabine Berteina-Raboin

Catalysts 2022, 12(1), 86; https://doi.org/10.3390/catal12010086 - 13 Jan 2022

Cited by 14 | Viewed by 3321

Abstract

This review describes the various synthetic methods commonly used to obtain molecules possessing conjugated dienes. We focus on methods involving cross-coupling reactions using various metals such as nickel, palladium, ruthenium, cobalt, cobalt/zinc, manganese, zirconium, or iron, mainly through examples that aimed to access natural molecules or their analogues. Among the natural molecules covered in this review, we discuss the total synthesis of a phytohormone, Acid Abscisic (ABA), carried out by our team involving the development of a conjugated diene chain. Full article

(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H Activation II)

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