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Carbonylation Chemistry
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Carbonylation Chemistry

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

Deadline for manuscript submissions: closed (31 May 2014) | Viewed by 41376

Special Issue Editor

Prof. Dr. Bartolo Gabriele

E-Mail Website
Guest Editor
Department of Chemistry and Chemical Technologies, Via Pietro Bucci, 12/C, University of Calabria, 87036 Arcavacata di Rende (CS), Italy
Interests: new syntheses of high value added molecules through catalytic assembly of simple units; innovative syntheses of heterocyclic molecules of pharmaceutical, agrochemical, or applicative interest; carbonylation chemistry; use of non-conventional solvents in organic synthesis; synthesis and semi-synthesis of bioactive compounds of pharmaceutical or agrochemical interest; synthesis of new materials for advanced applications; extraction, characterization, and evaluation of the biological activity of bioactive principles from natural matrices
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Carbonylation chemistry is an emerging area in modern organic synthesis. While the use of carbon monoxide as a C-1 unit for the preparation of carbonylated compounds has been exploited by industry for a long time, the application of this methodology in academic laboratories is relatively recent. A strong input in this direction has been given by the development of novel and efficient catalysts, which are able to realize complex carbonylation processes that lead to high value added products. These new catalytic methods start from simple and readily available substrates, and occur under mild or relatively mild conditions. At present, carbonylation chemistry represents a powerful tool for direct, one-step preparation of a variety of carbonylated products in a multicomponent fashion. Consequently, carbonylation chemistry is progressively acquiring interest from those interested in synthesis.

The Special Issue scope is broad, and includes the elaboration of novel catalysts for performing already known carbonylation processes in a more efficient manner, as well as the development of new carbonylation methods for the synthesis of products of industrial interest, and of fine chemicals (including bioactive compounds).

Prof. Dr. Bartolo Gabriele
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

  • carbonylation
  • homogeneous catalysis
  • carbonylated compounds
  • organic synthesis

Published Papers (4 papers)

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Research

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932 KiB  
Article
3-(Methoxycarbonylmethylene)isobenzofuran-1-imines as a New Class of Potential Herbicides
by Fabrizio Araniti, Raffaella Mancuso, Ida Ziccarelli, Francesco Sunseri, Maria Rosa Abenavoli and Bartolo Gabriele
Molecules 2014, 19(6), 8261-8275; https://doi.org/10.3390/molecules19068261 - 18 Jun 2014
Cited by 12 | Viewed by 5909
Abstract
A novel class of potential herbicides, the 3-(methoxycarbonylmethylene) isobenzofuran-1-imines, has been discovered. The herbicidal activity has been tested on two particular molecules, (E)-methyl 2-[3-(butylimino)isobenzofuran-1(3H)-ylidene]acetate (1) and (E)-methyl 2-phenyl-2-[3-(phenylimino)isobenzofuran-1(3H)-ylidene]acetate (2), prepared by [...] Read more.
A novel class of potential herbicides, the 3-(methoxycarbonylmethylene) isobenzofuran-1-imines, has been discovered. The herbicidal activity has been tested on two particular molecules, (E)-methyl 2-[3-(butylimino)isobenzofuran-1(3H)-ylidene]acetate (1) and (E)-methyl 2-phenyl-2-[3-(phenylimino)isobenzofuran-1(3H)-ylidene]acetate (2), prepared by palladium-catalyzed oxidative carbonylation of 2-alkynylbenzamides. Both compounds 1 and 2 showed a strong phytotoxic effect on both shoot and root systems of Arabidopsis thaliana. The effects observed on the shoot were similar for both molecules, but while compound 1 showed a stronger effect on root parameters (such as primary root length, root hair and density, showing lower ED50 values), compound 2 caused important malformations in root morphology. Our results indicate that these molecules are very promising synthetic herbicides. Full article
(This article belongs to the Special Issue Carbonylation Chemistry)
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512 KiB  
Article
Cobalt-Catalyzed Methoxycarbonylation of Substituted Dichlorobenzenes as an Example of a Facile Radical Anion Nucleophilic Substitution in Chloroarenes
by Tatyana S. Khaibulova, Irina A. Boyarskaya, Evgeny Larionov and Vadim P. Boyarskiy
Molecules 2014, 19(5), 5876-5897; https://doi.org/10.3390/molecules19055876 - 06 May 2014
Cited by 8 | Viewed by 6682
Abstract
A thorough mechanistic study on cobalt-catalysed direct methoxycarbonylation reactions of chlorobenzenes in the presence of methyl oxirane on a wide range of substrates, including poly- and monochloro derivatives with multiple substituents, is reported. The results demonstrate that the reaction is potentially useful as [...] Read more.
A thorough mechanistic study on cobalt-catalysed direct methoxycarbonylation reactions of chlorobenzenes in the presence of methyl oxirane on a wide range of substrates, including poly- and monochloro derivatives with multiple substituents, is reported. The results demonstrate that the reaction is potentially useful as it proceeds under very mild conditions (t = 62 °C, PCO = 1 bar) and converts aryl chlorides to far more valuable products (especially ortho-substituted benzoic acids and esters) in high yields. This transformation also offers another opportunity for the utilization of environmentally harmful polychlorinated benzenes and biphenyls (PCBs). This study is the first to discover an unexpected universal positive ortho-effect: the proximity of any substituent (including Me, Ph, and MeO groups and halogen atoms) to the reaction centre accelerates the methoxycarbonylation in chlorobenzenes. The effect of the ortho-substituents is discussed in detail and explained in terms of a radical anion reaction mechanism. The advantages of the methoxycarbonylation as a model for the mechanistic study of radical anion reactions are also illustrated. Full article
(This article belongs to the Special Issue Carbonylation Chemistry)
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Review

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1465 KiB  
Review
Carbonylation of Ethene Catalysed by Pd(II)-Phosphine Complexes
by Gianni Cavinato and Luigi Toniolo
Molecules 2014, 19(9), 15116-15161; https://doi.org/10.3390/molecules190915116 - 22 Sep 2014
Cited by 40 | Viewed by 9845
Abstract
This review deals with olefin carbonylation catalysed by Pd(II)-phosphine complexes in protic solvents. In particular, the results obtained in the carbonylation with ethene are reviewed. After a short description of the basic concepts relevant to this catalysis, the review treats in greater details [...] Read more.
This review deals with olefin carbonylation catalysed by Pd(II)-phosphine complexes in protic solvents. In particular, the results obtained in the carbonylation with ethene are reviewed. After a short description of the basic concepts relevant to this catalysis, the review treats in greater details the influence of the bite angle, skeletal rigidity, electronic and steric bulk properties of the ligand on the formation of the products, which range from high molecular weight perfectly alternating polyketones to methyl propanoate. It is shown that the steric bulk plays a major role in directing the selectivity. Particular emphasis is given to the factors governing the very active and selective catalysis to methyl propanoate, including the mechanism of the catalytic cycles with diphosphine- and monophosphine-catalysts. A brief note on the synthesis of methyl propanoate using a “Lucite” type catalyst in ionic liquids is also illustrated. A chapter is dedicated to the carbonylation of olefins in aqueous reaction media. The nonalternating CO-ethene copolymerization is also treated. Full article
(This article belongs to the Special Issue Carbonylation Chemistry)
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687 KiB  
Review
Formylation of Amines
by Ciera J. Gerack and Lisa McElwee-White
Molecules 2014, 19(6), 7689-7713; https://doi.org/10.3390/molecules19067689 - 10 Jun 2014
Cited by 118 | Viewed by 18232
Abstract
Methods to convert amines to formamides are of interest due to the many uses of formamides as synthetic intermediates. These methods include stoichiometric reactions of formylating reagents and catalytic reactions with CO as the carbonyl source. This review discusses the reported stoichiometric and [...] Read more.
Methods to convert amines to formamides are of interest due to the many uses of formamides as synthetic intermediates. These methods include stoichiometric reactions of formylating reagents and catalytic reactions with CO as the carbonyl source. This review discusses the reported stoichiometric and catalytic approaches for preparation of formamides. Full article
(This article belongs to the Special Issue Carbonylation Chemistry)
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