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Catalysts
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Metal Promoted Cyclocarbonylation Reactions in the Synthesis of Heterocycles
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Metal Promoted Cyclocarbonylation Reactions in the Synthesis of Heterocycles

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 October 2021) | Viewed by 28940

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Dr. Laura Antonella Aronica

E-Mail Website
Guest Editor
Dipartimento di Chimica e Chimica Industriale, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy
Interests: carbonylative cross-coupling; catalyzed synthesis of oxygen and nitrogen heterocycles; silylcarbocyclization reactions; heterogeneous catalysis

Special Issue Information

Dear Colleagues,

Oxygen and nitrogen heterocycle systems are found in a vast number of natural substrates and biologically active molecules such as antimycotics, antibiotics, antioxidants, pigments, and fluorophores. Therefore, several procedures dedicated to the building of such heterocycles have been developed. Many of them are based on the cyclization of suitable substrates, multi-component reactions, and ring expansion processes.

In this field, metal-catalyzed cyclocarbonylative reactions represent atom-economical and efficient methods for the synthesis of several functionalized compounds. Indeed, when the cyclization reaction is performed under CO pressure or in the presence of its surrogates the potentiality of the process is enhanced since the formation of the ring takes place with the contemporary introduction of the carbonyl functional group.

This Special Issue will focus on metal-catalyzed cyclocarbonylation reactions applied to the synthesis of heterocyclic rings of different sizes, including diastereoselective and enantioselective approaches, homogeneous and heterogeneous metal catalysis, and the application of these reactions to the total synthesis of natural products.

Submissions are very much welcome in the form of original research papers or short reviews that reflect the state-of-the-art of this research area.

Dr. Laura Antonella Aronica
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

  • Carbonylation
  • Coupling reactions
  • Cyclization
  • N-heterocycles
  • O-heterocycles
  • Heterogeneous or homogeneous catalysts

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Published Papers (6 papers)

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Editorial

Jump to: Research, Review

3 pages, 177 KiB  
Editorial
Metal Promoted Cyclocarbonylation Reactions in the Synthesis of Heterocycles
by Laura Antonella Aronica
Catalysts 2022, 12(4), 353; https://doi.org/10.3390/catal12040353 - 22 Mar 2022
Viewed by 1874
Abstract
Oxygen and nitrogen heterocycle systems are found in a vast number of natural substrates and biologically active molecules such as antimycotics, antibiotics, antitumors and antioxidants, in addition to pigments and fluorophores [...] Full article
(This article belongs to the Special Issue Metal Promoted Cyclocarbonylation Reactions in the Synthesis of Heterocycles)

Research

Jump to: Editorial, Review

15 pages, 2597 KiB  
Article
Flow Pd(II)-Catalysed Carbonylative Cyclisation in the Total Synthesis of Jaspine B
by Pavol Lopatka, Michal Gavenda, Martin Markovič, Peter Koóš and Tibor Gracza
Catalysts 2021, 11(12), 1513; https://doi.org/10.3390/catal11121513 - 12 Dec 2021
Cited by 3 | Viewed by 2434
Abstract
This work describes the total synthesis of jaspine B involving the highly diastereoselective Pd(II)-catalysed carbonylative cyclisation in the preparation of crucial intermediates. New conditions for this transformation were developed and involved the pBQ/LiCl as a reoxidation system and Fe(CO)5 as an [...] Read more.
This work describes the total synthesis of jaspine B involving the highly diastereoselective Pd(II)-catalysed carbonylative cyclisation in the preparation of crucial intermediates. New conditions for this transformation were developed and involved the pBQ/LiCl as a reoxidation system and Fe(CO)5 as an in situ source of stoichiometric amount of carbon monoxide (1.5 molar equivalent). In addition, we have demonstrated the use of a flow reactor adopting proposed conditions in the large-scale preparation of key lactones. Full article
(This article belongs to the Special Issue Metal Promoted Cyclocarbonylation Reactions in the Synthesis of Heterocycles)
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11 pages, 2043 KiB  
Article
Cr-Phthalocyanine Porous Organic Polymer as an Efficient and Selective Catalyst for Mono Carbonylation of Epoxides to Lactones
by Vinothkumar Ganesan and Sungho Yoon
Catalysts 2020, 10(8), 905; https://doi.org/10.3390/catal10080905 - 8 Aug 2020
Cited by 11 | Viewed by 3368
Abstract
A facile, one-pot design strategy to construct chromium(III)-phthalocyanine chlorides (Pc’CrCl) to form porous organic polymer (POP-Pc’CrCl) using solvent knitting Friedel-Crafts reaction (FCR) is described. The generated highly porous POP-Pc’CrCl is functionalized by post-synthetic exchange reaction with nucleophilic cobaltate ions to provide an heterogenized [...] Read more.
A facile, one-pot design strategy to construct chromium(III)-phthalocyanine chlorides (Pc’CrCl) to form porous organic polymer (POP-Pc’CrCl) using solvent knitting Friedel-Crafts reaction (FCR) is described. The generated highly porous POP-Pc’CrCl is functionalized by post-synthetic exchange reaction with nucleophilic cobaltate ions to provide an heterogenized carbonylation catalyst (POP-Pc’CrCo(CO)4) with Lewis acid-base type bimetallic units. The produced porous polymeric catalyst is identical to that homogeneous counterpart in structure and coordination environments. The catalyst is very selective and effective for mono carbonylation of epoxide into corresponding lactone and the activities are comparable to those observed for a homogeneous Pc’CrCo(CO)4 catalyst. The (POP-Pc’CrCo(CO)4) also displayed a good catalytic activities and recyclability upon successive recycles. Full article
(This article belongs to the Special Issue Metal Promoted Cyclocarbonylation Reactions in the Synthesis of Heterocycles)
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Review

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25 pages, 6979 KiB  
Review
Evolution of Pauson-Khand Reaction: Strategic Applications in Total Syntheses of Architecturally Complex Natural Products (2016–2020)
by Sijia Chen, Chongguo Jiang, Nan Zheng, Zhen Yang and Lili Shi
Catalysts 2020, 10(10), 1199; https://doi.org/10.3390/catal10101199 - 16 Oct 2020
Cited by 31 | Viewed by 7661
Abstract
Metal-mediated cyclizations are important transformations in a natural product total synthesis. The Pauson-Khand reaction, particularly powerful for establishing cyclopentenone-containing structures, is distinguished as one of the most attractive annulation processes routinely employed in synthesis campaigns. This review covers Co, Rh, and Pd catalyzed [...] Read more.
Metal-mediated cyclizations are important transformations in a natural product total synthesis. The Pauson-Khand reaction, particularly powerful for establishing cyclopentenone-containing structures, is distinguished as one of the most attractive annulation processes routinely employed in synthesis campaigns. This review covers Co, Rh, and Pd catalyzed Pauson-Khand reaction and summarizes its strategic applications in total syntheses of structurally complex natural products in the last five years. Additionally, the hetero-Pauson-Khand reaction in the synthesis of heterocycles will also be discussed. Focusing on the panorama of organic synthesis, this review highlights the strategically developed Pauson-Khand reaction in fulfilling total synthetic tasks and its synthetic attractiveness is aimed to be illustrated. Full article
(This article belongs to the Special Issue Metal Promoted Cyclocarbonylation Reactions in the Synthesis of Heterocycles)
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Graphical abstract

26 pages, 11622 KiB  
Review
Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis
by Xiao-Qiang Hu, Zi-Kui Liu and Wen-Jing Xiao
Catalysts 2020, 10(9), 1054; https://doi.org/10.3390/catal10091054 - 14 Sep 2020
Cited by 24 | Viewed by 8746
Abstract
Visible light photocatalytic radical carbonylation has been established as a robust tool for the efficient synthesis of carbonyl-containing compounds. Acyl radicals serve as the key intermediates in these useful transformations and can be generated from the addition of alkyl or aryl radicals to [...] Read more.
Visible light photocatalytic radical carbonylation has been established as a robust tool for the efficient synthesis of carbonyl-containing compounds. Acyl radicals serve as the key intermediates in these useful transformations and can be generated from the addition of alkyl or aryl radicals to carbon monoxide (CO) or various acyl radical precursors such as aldehydes, carboxylic acids, anhydrides, acyl chlorides or α-keto acids. In this review, we aim to summarize the impact of visible light-induced acyl radical carbonylation reactions on the synthesis of oxygen and nitrogen heterocycles. The discussion is mainly categorized based on different types of acyl radical precursors. Full article
(This article belongs to the Special Issue Metal Promoted Cyclocarbonylation Reactions in the Synthesis of Heterocycles)
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Scheme 1

31 pages, 22767 KiB  
Review
From Alkynes to Heterocycles through Metal-Promoted Silylformylation and Silylcarbocyclization Reactions
by Gianluigi Albano and Laura Antonella Aronica
Catalysts 2020, 10(9), 1012; https://doi.org/10.3390/catal10091012 - 3 Sep 2020
Cited by 15 | Viewed by 3863
Abstract
Oxygen and nitrogen heterocyclic systems are present in a large number of natural and synthetic compounds. In particular, oxa- and aza-silacyclane, tetrahydrofuran, benzofuran, cycloheptadifuranone, cycloheptadipyrrolone, pyrrolidine, lactone, lactam, phthalan, isochromanone, tetrahydroisoquinolinone, benzoindolizidinone, indoline and indolizidine scaffolds are present in many classes of biologically [...] Read more.
Oxygen and nitrogen heterocyclic systems are present in a large number of natural and synthetic compounds. In particular, oxa- and aza-silacyclane, tetrahydrofuran, benzofuran, cycloheptadifuranone, cycloheptadipyrrolone, pyrrolidine, lactone, lactam, phthalan, isochromanone, tetrahydroisoquinolinone, benzoindolizidinone, indoline and indolizidine scaffolds are present in many classes of biologically active molecules. Most of these contain a C=O moiety which can be easily introduced using carbonylative reaction conditions. In this field, intramolecular silylformylation and silylcarbocyclization reactions may afford heterocyclic compounds containing a carbonyl functional group together with a vinylsilane moiety which can be further transformed. Considering these two aspects, in this review a detailed analysis of the literature data regarding the application of silylformylation and silylcarbocyclization reactions to the synthesis of several heterocyclic derivatives is reported. Full article
(This article belongs to the Special Issue Metal Promoted Cyclocarbonylation Reactions in the Synthesis of Heterocycles)
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