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Advances in Organometallic Chemistry—Papers of the Editorial Board Members (EBMs)

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

Deadline for manuscript submissions: closed (30 June 2021) | Viewed by 19215

Special Issue Editor

Prof. Dr. Michal Szostak

E-Mail Website
Guest Editor
Department of Chemistry, Rutgers University, 73 Warren St., Newark, NJ 07102, USA
Interests: amide bonds; N-heterocyclic carbenes; C-N activation; C-H activation; C-O activation; lanthanides; cross-coupling; catalysis; reductions; reductive couplings; radical chemistry; synthetic methodology; natural products
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue of Molecules is dedicated to recent advances in organometallic chemistry research, and comprises a diverse selection of exclusive papers of the Editorial Board Members (EBMs) of the Organometallic Chemistry Section. It focuses on highlighting recent interesting investigations conducted in the laboratories of our section’s EBMs and represents our section as an attractive open-access publishing platform for physical chemistry research data.

Prof. Dr. Michal Szostak
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

  • organometallics
  • ligands
  • catalysis
  • transition metal complexes

Published Papers (7 papers)

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Research

27 pages, 8355 KiB  
Article
A Comprehensive Analysis of the Metal–Nitrile Bonding in an Organo-Diiron System
by Giulio Bresciani, Lorenzo Biancalana, Guido Pampaloni, Stefano Zacchini, Gianluca Ciancaleoni and Fabio Marchetti
Molecules 2021, 26(23), 7088; https://doi.org/10.3390/molecules26237088 - 23 Nov 2021
Cited by 19 | Viewed by 2138
Abstract
Nitriles (N≡CR) are ubiquitous in coordination chemistry, yet literature studies on metal–nitrile bonding based on a multi-technique approach are rare. We selected an easily-available di-organoiron framework, containing both π-acceptor (CO, aminocarbyne) and donor (Cp = η5−C5H5) ligands, [...] Read more.
Nitriles (N≡CR) are ubiquitous in coordination chemistry, yet literature studies on metal–nitrile bonding based on a multi-technique approach are rare. We selected an easily-available di-organoiron framework, containing both π-acceptor (CO, aminocarbyne) and donor (Cp = η5−C5H5) ligands, as a suitable system to provide a comprehensive description of the iron–nitrile bond. Thus, the new nitrile (2–12)CF3SO3 and the related imine/amine complexes (8–9)CF3SO3 were synthesized in 58–83% yields from the respective tris-carbonyl precursors (1a–d)CF3SO3, using the TMNO strategy (TMNO = trimethylamine-N-oxide). The products were fully characterized by elemental analysis, IR (solution and solid state) and multinuclear NMR spectroscopy. In addition, the structures of (2)CF3SO3, (3)CF3SO3, (5)CF3SO3 and (11)CF3SO3 were ascertained by single crystal X-ray diffraction. Salient spectroscopic data of the nitrile complexes are coherent with the scale of electron-donor power of the R substituents; otherwise, this scale does not match the degree of Fe → N π-back-donation and the Fe–N bond energies, which were elucidated in (2–7)CF3SO3 by DFT calculations. Full article
(This article belongs to the Special Issue Advances in Organometallic Chemistry—Papers of the Editorial Board Members (EBMs))
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17 pages, 2154 KiB  
Article
Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them
by Nikita S. Gudim, Ekaterina A. Knyazeva, Ludmila V. Mikhalchenko, Ivan S. Golovanov, Vadim V. Popov, Natalia V. Obruchnikova and Oleg A. Rakitin
Molecules 2021, 26(16), 4931; https://doi.org/10.3390/molecules26164931 - 14 Aug 2021
Cited by 16 | Viewed by 3264
Abstract
This paper presents an improved synthesis of 4,7-dibromobenzo[d][1,2,3]thiadiazole from commercially available reagents. According to quantum-mechanical calculations, benzo[d][1,2,3]thiadiazole (isoBTD) has higher values of ELUMO and energy band gap (Eg), which indicates high electron conductivity, occurring due to [...] Read more.
This paper presents an improved synthesis of 4,7-dibromobenzo[d][1,2,3]thiadiazole from commercially available reagents. According to quantum-mechanical calculations, benzo[d][1,2,3]thiadiazole (isoBTD) has higher values of ELUMO and energy band gap (Eg), which indicates high electron conductivity, occurring due to the high stability of the molecule in the excited state. We studied the cross-coupling reactions of this dibromide and found that the highest yields of π-spacer–acceptor–π-spacer type compounds were obtained by means of the Stille reaction. Therefore, 6 new structures of this type have been synthesized. A detailed study of the optical and electrochemical properties of the obtained π-spacer–acceptor–π-spacer type compounds in comparison with isomeric structures based on benzo[c][1,2,5]thiadiazole (BTD) showed a red shift of absorption maxima with lower absorptive and luminescent capacity. However, the addition of the 2,2′-bithiophene fragment as a π-spacer resulted in an unexpected increase of the extinction coefficient in the UV/vis spectra along with a blue shift of both absorption maxima for the isoBTD-based compound as compared to the BTD-based compound. Thus, a thorough selection of components in the designing of appropriate compounds with benzo[d][1,2,3]thiadiazole as an internal acceptor can lead to promising photovoltaic materials. Full article
(This article belongs to the Special Issue Advances in Organometallic Chemistry—Papers of the Editorial Board Members (EBMs))
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17 pages, 31063 KiB  
Article
Facile N9-Alkylation of Xanthine Derivatives and Their Use as Precursors for N-Heterocyclic Carbene Complexes
by Moloud Mokfi, Jörg Rust, Christian W. Lehmann and Fabian Mohr
Molecules 2021, 26(12), 3705; https://doi.org/10.3390/molecules26123705 - 17 Jun 2021
Cited by 3 | Viewed by 2094
Abstract
The xanthine-derivatives 1,3,7-trimethylxanthine, 1,3-dimethyl-7-benzylxanthine and 1,3-dimethyl-7-(4-chlorobenzyl)xanthine are readily ethylated at N9 using the cheap alkylating agents ethyl tosylate or diethyl sulfate. The resulting xanthinium tosylate or ethyl sulfate salts can be converted into the corresponding PF6− and chloride salts. The reaction [...] Read more.
The xanthine-derivatives 1,3,7-trimethylxanthine, 1,3-dimethyl-7-benzylxanthine and 1,3-dimethyl-7-(4-chlorobenzyl)xanthine are readily ethylated at N9 using the cheap alkylating agents ethyl tosylate or diethyl sulfate. The resulting xanthinium tosylate or ethyl sulfate salts can be converted into the corresponding PF6− and chloride salts. The reaction of these xanthinium salts with silver(I) oxide results in the formation of different silver(I) carbene-complexes. In the presence of ammonia, ammine complexes [Ag(NHC)(NH3)]PF6 are formed, whilst with Et2NH, the bis(carbene) salts [Ag(NHC)2]PF6 were isolated. Using the xanthinium chloride salts neutral silver(I) carbenes [Ag(NHC)Cl] were prepared. These silver complexes were used in a variety of transmetallation reactions to give the corresponding gold(I), ruthenium(II) as well as rhodium(I) and rhodium(III) complexes. The compounds were characterized by various spectroscopic methods as well as X-ray diffraction. Full article
(This article belongs to the Special Issue Advances in Organometallic Chemistry—Papers of the Editorial Board Members (EBMs))
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19 pages, 4803 KiB  
Article
Dendrimers Functionalized with Palladium Complexes of N-, N,N-, and N,N,N-Ligands
by Quentin Vanbellingen, Paul Servin, Anaïs Coinaud, Sonia Mallet-Ladeira, Régis Laurent and Anne-Marie Caminade
Molecules 2021, 26(8), 2333; https://doi.org/10.3390/molecules26082333 - 17 Apr 2021
Cited by 3 | Viewed by 1797
Abstract
Pyridine, pyridine imine, and bipyridine imine ligands functionalized by a phenol have been synthesized and characterized, in many cases by X-ray diffraction. Several of these N-, N,N-, and N,N,N,-ligands have been grafted onto the surface of phosphorhydrazone dendrimers, from generation 1 to generation [...] Read more.
Pyridine, pyridine imine, and bipyridine imine ligands functionalized by a phenol have been synthesized and characterized, in many cases by X-ray diffraction. Several of these N-, N,N-, and N,N,N,-ligands have been grafted onto the surface of phosphorhydrazone dendrimers, from generation 1 to generation 3. The complexation ability of these monomers and dendrimers towards palladium(II) has been assayed. The corresponding complexes have been either isolated or prepared in situ. In both cases, the monomeric and dendritic complexes have been tested as catalysts in Heck couplings and in Sonogashira couplings. In some cases, a positive dendritic effect has been observed, that is, an increase of the catalytic efficiency proportional to the dendrimer generation. Full article
(This article belongs to the Special Issue Advances in Organometallic Chemistry—Papers of the Editorial Board Members (EBMs))
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8 pages, 2630 KiB  
Article
Transamidation of Amides and Amidation of Esters by Selective N–C(O)/O–C(O) Cleavage Mediated by Air- and Moisture-Stable Half-Sandwich Nickel(II)–NHC Complexes
by Jonathan Buchspies, Md. Mahbubur Rahman and Michal Szostak
Molecules 2021, 26(1), 188; https://doi.org/10.3390/molecules26010188 - 02 Jan 2021
Cited by 15 | Viewed by 3648
Abstract
The formation of amide bonds represents one of the most fundamental processes in organic synthesis. Transition-metal-catalyzed activation of acyclic twisted amides has emerged as an increasingly powerful platform in synthesis. Herein, we report the transamidation of N-activated twisted amides by selective N–C(O) [...] Read more.
The formation of amide bonds represents one of the most fundamental processes in organic synthesis. Transition-metal-catalyzed activation of acyclic twisted amides has emerged as an increasingly powerful platform in synthesis. Herein, we report the transamidation of N-activated twisted amides by selective N–C(O) cleavage mediated by air- and moisture-stable half-sandwich Ni(II)–NHC (NHC = N-heterocyclic carbenes) complexes. We demonstrate that the readily available cyclopentadienyl complex, [CpNi(IPr)Cl] (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), promotes highly selective transamidation of the N–C(O) bond in twisted N-Boc amides with non-nucleophilic anilines. The reaction provides access to secondary anilides via the non-conventional amide bond-forming pathway. Furthermore, the amidation of activated phenolic and unactivated methyl esters mediated by [CpNi(IPr)Cl] is reported. This study sets the stage for the broad utilization of well-defined, air- and moisture-stable Ni(II)–NHC complexes in catalytic amide bond-forming protocols by unconventional C(acyl)–N and C(acyl)–O bond cleavage reactions. Full article
(This article belongs to the Special Issue Advances in Organometallic Chemistry—Papers of the Editorial Board Members (EBMs))
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13 pages, 1948 KiB  
Article
Synthesis and Biological Studies on Dinuclear Gold(I) Complexes with Di-(N-Heterocyclic Carbene) Ligands Functionalized with Carbohydrates
by Federica Tresin, Valentina Stoppa, Marco Baron, Andrea Biffis, Alfonso Annunziata, Luigi D’Elia, Daria Maria Monti, Francesco Ruffo, Marco Roverso, Paolo Sgarbossa, Sara Bogialli and Cristina Tubaro
Molecules 2020, 25(17), 3850; https://doi.org/10.3390/molecules25173850 - 24 Aug 2020
Cited by 6 | Viewed by 2510
Abstract
The design of novel metal complexes with N-heterocyclic carbene (NHC) ligands that display biological activity is an active research field in organometallic chemistry. One of the possible approaches consists of the use of NHC ligands functionalized with a carbohydrate moiety. Two novel [...] Read more.
The design of novel metal complexes with N-heterocyclic carbene (NHC) ligands that display biological activity is an active research field in organometallic chemistry. One of the possible approaches consists of the use of NHC ligands functionalized with a carbohydrate moiety. Two novel Au(I)–Au(I) dinuclear complexes were synthesized; they present a neutral structure with one bridging diNHC ligand, having one or both heterocyclic rings decorated with a carbohydrate functionality. With the symmetric diNHC ligand, the dicationic dinuclear complex bearing two bridging diNHC ligands was also synthesized. The study was completed by analyzing the antiproliferative properties of these complexes, which were compared to the activity displayed by similar mononuclear Au(I) complexes and by the analogous bimetallic Au(I)–Au(I) complex not functionalized with carbohydrates. Full article
(This article belongs to the Special Issue Advances in Organometallic Chemistry—Papers of the Editorial Board Members (EBMs))
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10 pages, 2849 KiB  
Article
Cooperative Binding and Stepwise Encapsulation of Drug Molecules by Sulfonylcalixarene-Based Metal-Organic Supercontainers
by Tian-Pu Sheng, Xin-Xia Fan, Guo-Zong Zheng, Feng-Rong Dai and Zhong-Ning Chen
Molecules 2020, 25(11), 2656; https://doi.org/10.3390/molecules25112656 - 08 Jun 2020
Cited by 11 | Viewed by 2827
Abstract
The cooperative binding behavior of a face-directed octahedral metal-organic supercontainer featuring one endo cavity and six exo cavities was thoroughly examined in chloroform solution through ultraviolet-visible (UV-Vis) titration technique using two representative drug molecules as the guests. The titration curves and their nonlinear [...] Read more.
The cooperative binding behavior of a face-directed octahedral metal-organic supercontainer featuring one endo cavity and six exo cavities was thoroughly examined in chloroform solution through ultraviolet-visible (UV-Vis) titration technique using two representative drug molecules as the guests. The titration curves and their nonlinear fit to Hill equation strongly suggest the efficient encapsulation of the guest molecules by the synthetic host, which exhibit interesting cooperative and stepwise binding behavior. Based on the control experiments using tetranuclear complex as a reference, it is clear that two equivalents of the guest molecules are initially encapsulated inside the endo cavity, followed by the trapping of six additional equivalents of the drug molecules through six exo cavities (1 eq. per exo cavity), and the remaining guests are entrapped by the external pockets. The results provide an in-depth understanding of the cooperative binding behavior of metal-organic supercontainers, which opens up new opportunities for designing synthetic receptors for truly biomimetic functional applications. Full article
(This article belongs to the Special Issue Advances in Organometallic Chemistry—Papers of the Editorial Board Members (EBMs))
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