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Molecules
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Experimental and Theoretical Aspects of Catalytic Carbonylation Reactions
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Experimental and Theoretical Aspects of Catalytic Carbonylation Reactions

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

Deadline for manuscript submissions: closed (30 April 2022) | Viewed by 6717

Special Issue Editor

Dr. Tamás Kégl

E-Mail Website
Guest Editor
University of Pécs, Pécs, Hungary
Interests: homogeneous catalysis; theoretical inorganic and organometallic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The history of homogeneous catalytic carbonylation started when Otto Roelen discovered the cobalt catalyzed production of aldehydes from alkenes, that is, the hydroformylation reaction. Roelen’s seminal work is generally considered as the beginning of the era of homogeneous catalysis as well. Nowadays, the utilization of carbon monoxide as a carbonyl source of organic carbonyl compounds, such as ketons, aldehydes, carboxylic acids, and their derivatives in various transition metal-catalyzed reactions has become one of the most widespread methodology for homogeneous catalytic reactions. The unbelievably rich chemistry of homogeneous catalysis like carbon–carbon bond forming reactions or carbonylations of alkenes, alkines, ketones, oximes or azomethines have also provided products with sometimes unprecedented structures. During the last decades, several novel synthetic methods based on carbon monoxide have been reported; some of them are even fulfilled the criteria of green/sustainable chemistry.

The theme of this Special Issue of Molecules is “Experimental and theoretical aspects of catalytic carbonylation reactions”. I invite both reviews and current experimental and/or theoretical research contributions on all aspects of homogeneous carbonylation reactions.

Dr. Tamás Kégl
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 reactions
  • Hydroformylation
  • Hydroalkoxycarbonylation
  • Carbonylative coupling
  • Reaction mechanism

Published Papers (3 papers)

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Research

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16 pages, 2505 KiB  
Article
Stereoisomeric Tris-BINOL-Menthol Bulky Monophosphites: Synthesis, Characterisation and Application in Rhodium-Catalysed Hydroformylation
by Alexandre P. Felgueiras, Fábio M. S. Rodrigues, Rui M. B. Carrilho, Pedro F. Cruz, Vitor H. Rodrigues, Tamás Kégl, László Kollár and Mariette M. Pereira
Molecules 2022, 27(6), 1989; https://doi.org/10.3390/molecules27061989 - 19 Mar 2022
Cited by 3 | Viewed by 2137
Abstract
Four stereoisomeric monoether derivatives, based on axially chiral (R)- or (S)-BINOL bearing a chiral (+)- or (−)-neomenthyloxy group were synthesised and fully characterised by NMR spectroscopy and X-ray crystallography. The respective tris-monophosphites were thereof prepared and fully characterised. The [...] Read more.
Four stereoisomeric monoether derivatives, based on axially chiral (R)- or (S)-BINOL bearing a chiral (+)- or (−)-neomenthyloxy group were synthesised and fully characterised by NMR spectroscopy and X-ray crystallography. The respective tris-monophosphites were thereof prepared and fully characterised. The coordination ability of the new bulky phosphites with Rh(CO)2(acac), was attested by 31P NMR, which presented a doublet in the range of δ = 120 ppm, with a 1J(103Rh-31P) coupling constant of 290 Hz. The new tris-binaphthyl phosphite ligands were further characterised by DFT computational methods, which allowed us to calculate an electronic (CEP) parameter of 2083.2 cm−1 and an extremely large cone angle of 345°, decreasing to 265° upon coordination with a metal atom. Furthermore, the monophosphites were applied as ligands in rhodium-catalysed hydroformylation of styrene, leading to complete conversions in 4 h, 100% chemoselectivity for aldehydes and up to 98% iso-regioselectivity. The Rh(I)/phosphite catalytic system was also highly active and selective in the hydroformylation of disubstituted olefins, including (E)-prop-1-en-1-ylbenzene and prop-1-en-2-ylbenzene. Full article
(This article belongs to the Special Issue Experimental and Theoretical Aspects of Catalytic Carbonylation Reactions)
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12 pages, 1128 KiB  
Article
Interrupted Intramolecular Hydroaminomethylation of N-Protected-2-vinyl Anilines: Novel Access to 3-Substitued Indoles or Indoline-2-ols
by Frank Hochberger-Roa, Perla H. García-Ríos, José G. López-Cortés, M. Carmen Ortega-Alfaro, Jean-Claude Daran, Maryse Gouygou and Martine Urrutigoïty
Molecules 2022, 27(3), 1074; https://doi.org/10.3390/molecules27031074 - 05 Feb 2022
Cited by 1 | Viewed by 2019
Abstract
A new synthetic alternative to the synthesis of 3-methyl indoles and 3-methyl indoline-2-ols with an excellent atomic economy is presented in this study. It is demonstrated that the intramolecular interrupted hydroaminomethylation (HAM) reaction is a powerful tool for the formation of these compounds, [...] Read more.
A new synthetic alternative to the synthesis of 3-methyl indoles and 3-methyl indoline-2-ols with an excellent atomic economy is presented in this study. It is demonstrated that the intramolecular interrupted hydroaminomethylation (HAM) reaction is a powerful tool for the formation of these compounds, which exhibit wide-ranging biological activity. Several N-Protected-2-vinyl anilines were synthesized and involved in the reaction producing the corresponding 3-methylindole or 3-methyl indoline-2-ol depending on the nature of the N-protecting groups. Full article
(This article belongs to the Special Issue Experimental and Theoretical Aspects of Catalytic Carbonylation Reactions)
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Review

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19 pages, 1641 KiB  
Review
27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)
by Tímea R. Kégl, László T. Mika and Tamás Kégl
Molecules 2022, 27(2), 460; https://doi.org/10.3390/molecules27020460 - 11 Jan 2022
Cited by 9 | Viewed by 2137
Abstract
Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a vast number of applications for the synthesis [...] Read more.
Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a vast number of applications for the synthesis of simple building blocks as well as for the functionalization of biologically important skeletons. This review covers the history of carbonylative coupling reactions in Hungary between the years 1994 and 2021. Full article
(This article belongs to the Special Issue Experimental and Theoretical Aspects of Catalytic Carbonylation Reactions)
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