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Organometallic Chemistry
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Organometallic Chemistry

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (30 April 2011) | Viewed by 68413

Special Issue Editor

Prof. Dr. Brian J. Frost

E-Mail Website
Guest Editor
Department of Chemistry, University of Nevada, Reno, NV, USA
Interests: aqueous organometallic chemistry; mechanistic organometallic chemistry; biphasic catalysis; water soluble phosphine ligands; green chemistry

Special Issue Information

Dear Colleagues,

Organometallic chemistry is a broadly defined area at the intersection of inorganic and organic chemistry. The chemistry of compounds containing metal carbon and metal hydrogen bonds has been extensively explored and continues to dominate much of the research in catalysis. Over the years organometallic complexes and compounds have found tremendous utility in numerous areas including, but not limited to, organic synthesis, catalysis, and medicinal chemistry. The focus of this special issue is to present papers that cover the wide range of organometallic chemistry including: synthesis, structure, and reactivity of compounds containing metal carbon bonds. Organometallic complexes with applications in medicinal chemistry, catalysis, or other synthetically useful transformations will be of particular interest. For the purposes of this special issue any isolable compound, proposed intermediate, or transition state containing a metal or metalloid with a bonding interaction to carbon or hydrogen will be considered "organometallic". Manuscripts "in the spirit" of organometallic chemistry will also be considered.

Prof. Dr. Brian J. Frost
Guest Editor

Keywords

  • catalysis
  • metal catalyzed organic transformations
  • organotransition metal chemistry
  • mechanistic organometallic chemistry
  • biologically active organometallic compounds
  • metal hydrides
  • organometallic reactions in alternative media
  • aqueous organometallic chemistry

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Published Papers (8 papers)

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Research

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620 KiB  
Article
The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands
by Jason A. Weeden, Rongcai Huang, Kathryn D. Galloway, Phillip W. Gingrich and Brian J. Frost
Molecules 2011, 16(8), 6215-6231; https://doi.org/10.3390/molecules16086215 - 25 Jul 2011
Cited by 29 | Viewed by 8246
Abstract
The synthesis and structure of palladium complexes of trisubstituted PTA derivatives, PTAR3, are described. Water-soluble phosphine ligands 1,3,5-triaza-7-phosphaadmantane (PTA), tris(aminomethyl)phosphine trihydrobromide, tri(aminomethyl) phosphine, 3,7-dimethyl-1,5,7-triaza-3-phosphabicyclo[3,3,1]nonane (RO-PTA), 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA), lithium 1,3,5-triaza-7-phosphaadamantane-6-carboxylate (PTA-CO2Li), 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo [3.3.1.1]decane, and 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane were used as ligands for [...] Read more.
The synthesis and structure of palladium complexes of trisubstituted PTA derivatives, PTAR3, are described. Water-soluble phosphine ligands 1,3,5-triaza-7-phosphaadmantane (PTA), tris(aminomethyl)phosphine trihydrobromide, tri(aminomethyl) phosphine, 3,7-dimethyl-1,5,7-triaza-3-phosphabicyclo[3,3,1]nonane (RO-PTA), 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA), lithium 1,3,5-triaza-7-phosphaadamantane-6-carboxylate (PTA-CO2Li), 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo [3.3.1.1]decane, and 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane were used as ligands for palladium catalyzed Suzuki reactions in aqueous media. RO-PTA in combination with palladium acetate or palladium chloride was the most active catalyst for Suzuki cross coupling of aryl bromides and phenylboronic acid at 80 °C in 1:1 water:acetonitrile. The activity of Pd(II) complexes of RO-PTA is comparable to PPh2(m-C6H4SO3Na) (TPPMS) and P(m-C6H4SO3Na)3 (TPPTS) and less active than tri(4,6-dimethyl-3-sulfonatophenyl)phosphine trisodium salt (TXPTS). Activated, deactivated, and sterically hindered aryl bromides were examined, with yields ranging from 50% to 90% in 6 h with 5% palladium precatalyst loading. X-ray crystal structures of (RO-PTA)PdCl2, (PTAR3)2PdCl2 (R = Ph, p-tert-butylC6H5), and PTAR3 (R = p-tert-butylC6H5) are reported. Full article
(This article belongs to the Special Issue Organometallic Chemistry)
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469 KiB  
Article
Bent Dinuclear Platinum(II) Halo-Bridged Carbonyl Complexes
by Daniela Belli Dell'Amico, Luca Labella and Fabio Marchetti
Molecules 2011, 16(7), 6082-6091; https://doi.org/10.3390/molecules16076082 - 20 Jul 2011
Cited by 1 | Viewed by 5747
Abstract
Crystals of trans-Pt2(μ-X)2X2(CO)2 (X = Br, I) have been grown and their molecular and crystalline structures have been solved by X-ray diffraction methods. In both cases the dinuclear molecules are bent, with a [...] Read more.
Crystals of trans-Pt2(μ-X)2X2(CO)2 (X = Br, I) have been grown and their molecular and crystalline structures have been solved by X-ray diffraction methods. In both cases the dinuclear molecules are bent, with a bending angle of 164.6° and 156.5° for the bromide and the iodide, respectively. While the structure of the bromo-derivative is reported here for the first time, a modification of trans-Pt2(μ-I)2I2(CO)2 with planar centrosymmetric molecules is known. This appears to be a rare case of a platinum(II) halo-bridged derivative structurally characterized in both bent and planar forms. Full article
(This article belongs to the Special Issue Organometallic Chemistry)
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392 KiB  
Article
Synthesis and Spectroscopic Characterization of Two Tetrasubstituted Cationic Porphyrin Derivatives
by Antonio E.H. Machado, Weverson R. Gomes, Diesley M.S. Araújo, Hércules S. Miglio, Leonardo T. Ueno, Rodrigo De Paula, José A.S. Cavaleiro and Newton M. Barbosa Neto
Molecules 2011, 16(7), 5807-5821; https://doi.org/10.3390/molecules16075807 - 8 Jul 2011
Cited by 12 | Viewed by 8344
Abstract
An imidazolium tetrasubstituted cationic porphyrin derivative (the free base and its Zn(II) complex) with five-membered heterocyclic groups in the meso-positions were synthesized using microwave irradiation, and the compounds obtained characterized by 1H-NMR and mass spectrometry. We observed that under microwave irradiation [...] Read more.
An imidazolium tetrasubstituted cationic porphyrin derivative (the free base and its Zn(II) complex) with five-membered heterocyclic groups in the meso-positions were synthesized using microwave irradiation, and the compounds obtained characterized by 1H-NMR and mass spectrometry. We observed that under microwave irradiation the yield is similar to when the synthesis is performed under conventional heating, however, the time required to prepare the porphyrins decreases enormously. In order to investigate the electronic state of these compounds, we employed UV-Vis and fluorescence spectroscopy combined with quantum chemical calculations. The results reveal the presence, in both compounds, of a large number of electronic states involving the association between the Soret and a blue-shifted band. The Soret band in both compounds also shows a considerable solvent dependence. As for emission, these compounds present low quantum yield at room temperature and no solvent influence on the fluorescence spectra was observed. Full article
(This article belongs to the Special Issue Organometallic Chemistry)
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486 KiB  
Article
On the π Coordination of Organometallic Fullerene Complexes
by Bertha Molina, Liliana Pérez-Manriquez and Roberto Salcedo
Molecules 2011, 16(6), 4652-4659; https://doi.org/10.3390/molecules16064652 - 3 Jun 2011
Cited by 9 | Viewed by 6010
Abstract
Novel organometallic complexes of fullerene C80 and aryl ligands were simulated. The nature and characteristics of this family of complexes involving π coordination between the fullerene and a metal centre have been studied from a theoretical point of view. We are particularly [...] Read more.
Novel organometallic complexes of fullerene C80 and aryl ligands were simulated. The nature and characteristics of this family of complexes involving π coordination between the fullerene and a metal centre have been studied from a theoretical point of view. We are particularly interested in complexes where η6 coordination is present, this being the strangest manifestation of known coordinations, and thus we have studied several known and simulated compounds of this kind in order to understand the lack of examples. The presence of other η6 or η5 ligands on the opposite side seems to be an important element aiding the stabilization of these complexes, also inducing the conductive and semiconductive behaviour of the studied species. Full article
(This article belongs to the Special Issue Organometallic Chemistry)
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225 KiB  
Article
RuCl3·3H2O Catalyzed Reactions: Facile Synthesis of Bis(indolyl)methanes under Mild Conditions
by Hong-En Qu, Chen Xiao, Ning Wang, Kai-Hui Yu, Qiao-Sheng Hu and Liang-Xian Liu
Molecules 2011, 16(5), 3855-3868; https://doi.org/10.3390/molecules16053855 - 9 May 2011
Cited by 50 | Viewed by 8965
Abstract
RuCl3·3H2O was found to be an effective catalyst for reactions of indoles, 2-methylthiophene, and 2-methylfuran with aldehydes to afford the corresponding bis(indolyl)methanes, bis(thienyl)methanes, and bis(fur-2-yl)methanes in moderate to excellent yields. Experimental results indicated that mono(indolyl)methanol is not the reaction [...] Read more.
RuCl3·3H2O was found to be an effective catalyst for reactions of indoles, 2-methylthiophene, and 2-methylfuran with aldehydes to afford the corresponding bis(indolyl)methanes, bis(thienyl)methanes, and bis(fur-2-yl)methanes in moderate to excellent yields. Experimental results indicated that mono(indolyl)methanol is not the reaction intermediate under these reaction conditions. Full article
(This article belongs to the Special Issue Organometallic Chemistry)
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221 KiB  
Article
Irving-Williams Order in the Framework of Connectivity Index 3χv Enables Simultaneous Prediction of Stability Constants of Bivalent Transition Metal Complexes
by Ante Miličević, Gina Branica and Nenad Raos
Molecules 2011, 16(2), 1103-1112; https://doi.org/10.3390/molecules16021103 - 26 Jan 2011
Cited by 29 | Viewed by 11079
Abstract
Logarithms of stability constants, log K1 and log β2, of the first transition series metal mono- and bis-complexes with any of four aliphatic amino acids (glycine, alanine, valine and leucine) decrease monotonously with third order valence connectivity index, [...] Read more.
Logarithms of stability constants, log K1 and log β2, of the first transition series metal mono- and bis-complexes with any of four aliphatic amino acids (glycine, alanine, valine and leucine) decrease monotonously with third order valence connectivity index, 3χv, from Cu2+ to Mn2+. While stability of the complexes with the same metal is linearly dependent on 3χv, stability constants of Mn2+, Fe2+, Co2+, and Ni2+complexes with the same ligand show a quadratic dependence on 3χv. As Cu2+ complexes deviate significantly from quadratic functions, models for the simultaneous estimation of the stability constants, yielding r = 0.999 (S.E. = 0.05) and r = 0.998 (S.E. = 0.11), for log K1 and log β2, respectively, were developed only for Mn2+, Fe2+, Co2+, and Ni2+ complexes with amino acids. Full article
(This article belongs to the Special Issue Organometallic Chemistry)
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413 KiB  
Article
New Chiral Phosphoramidite Complexes of Iron as Catalytic Precursors in the Oxidation of Activated Methylene Groups
by Pushkar Shejwalkar, Nigam P. Rath and Eike B. Bauer
Molecules 2010, 15(4), 2631-2650; https://doi.org/10.3390/molecules15042631 - 12 Apr 2010
Cited by 14 | Viewed by 9238
Abstract
New phosphoramidite complexes of iron were synthesized and structurally characterized. Reaction of the known chiral phosphoramidites (RO)2PNR’2 (R = binaphthyl, R’ = CH3, 1a; R = binaphthyl, R’ = benzyl, 1b) with [FeBr(Cp)(CO)2] afforded [...] Read more.
New phosphoramidite complexes of iron were synthesized and structurally characterized. Reaction of the known chiral phosphoramidites (RO)2PNR’2 (R = binaphthyl, R’ = CH3, 1a; R = binaphthyl, R’ = benzyl, 1b) with [FeBr(Cp)(CO)2] afforded the title compounds [FeBr(Cp)(CO)(1a,b)] (4a,b) in 34 and 65 % isolated yields as mixtures of diastereomers, since both the metal and the ligand are stereogenic. Similarly, reaction of 1b with [Fe(Cp)I(CO)2] in the presence of catalytic [Fe(Cp)(CO)2]2 afforded [Fe(Cp)I(CO)(1b)] (5b) in 81% yield as a mixture of diastereomers. The molecular structures of 4a, 4b and 5 were determined, revealing a pseudo octahedral coordination geometry about the iron center. The new metal complexes are catalytically active in the oxidation of benzylic methylene groups to the corresponding ketones, utilizing t-BuOOH as oxidant (2 mol% catalyst, 36 h, room temperature, 31−80% yield). Full article
(This article belongs to the Special Issue Organometallic Chemistry)
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Review

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418 KiB  
Review
Synthesis, Properties Characterization and Applications of Various Organobismuth Compounds
by Jingfei Luan, Lingyan Zhang and Zhitian Hu
Molecules 2011, 16(5), 4191-4230; https://doi.org/10.3390/molecules16054191 - 20 May 2011
Cited by 45 | Viewed by 9816
Abstract
Organobismuth chemistry was emphasized in this review article due to the low price, low toxicity and low radioactivity characteristics of bismuth. As an environmentally-friendly class of organometallic compounds, different types of organobismuth compounds have been used in organic synthesis, catalysis, materials, etc. The [...] Read more.
Organobismuth chemistry was emphasized in this review article due to the low price, low toxicity and low radioactivity characteristics of bismuth. As an environmentally-friendly class of organometallic compounds, different types of organobismuth compounds have been used in organic synthesis, catalysis, materials, etc. The synthesis and property characterization of many organobismuth compounds had been summarized. This review article also presented a survey of various applications of organobismuth compounds in organic transformations, as reagents or catalysts. The reactivity, reaction pathways and mechanisms of reactions with organobismuths were discussed. Less common and limiting aspects of organobismuth compounds were also briefly mentioned. Full article
(This article belongs to the Special Issue Organometallic Chemistry)
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