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Search for "organometallic" in Full Text gives 327 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

  • Shaojin Gu,
  • Jiehao Du,
  • Jingjing Huang,
  • Huan Xia,
  • Ling Yang,
  • Weilin Xu and
  • Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

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  • atmosphere at room temperature. Keywords: copper; CuAAC reaction; : N-heterocylic carbene; 1,2,3-triazole; Introduction N-Heterocyclic carbene (NHC) have interesting electronic and structural properties. This resulted in their use as versatile ligands in organometallic chemistry and homogeneous catalysis
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Published 03 May 2016

Indenopyrans – synthesis and photoluminescence properties

  • Andreea Petronela Diac,
  • Ana-Maria Ţepeş,
  • Albert Soran,
  • Ion Grosu,
  • Anamaria Terec,
  • Jean Roncali and
  • Elena Bogdan

Beilstein J. Org. Chem. 2016, 12, 825–834, doi:10.3762/bjoc.12.81

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  • Andreea Petronela Diac Ana-Maria Tepes Albert Soran Ion Grosu Anamaria Terec Jean Roncali Elena Bogdan Babeş-Bolyai University, Center of Supramolecular Organic and Organometallic Chemistry (CSOOMC) Cluj-Napoca, 11 Arany Janos, 400028 Cluj-Napoca, Romania Group Linear Conjugated Systems, CNRS
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Published 27 Apr 2016

Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes

  • M. Emin Cinar,
  • Bernward Engelen,
  • Martin Panthöfer,
  • Hans-Jörg Deiseroth,
  • Jens Schlirf and
  • Michael Schmittel

Beilstein J. Org. Chem. 2016, 12, 813–824, doi:10.3762/bjoc.12.80

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  • analyzing the harmonic vibrational frequencies, using analytical second derivatives. To predict the energies plausibly, as recommended for organometallic compounds, single point calculations with M06 functional [52] were performed using the same basis sets (Scheme 6). Complexation of the metal enolate E
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Published 27 Apr 2016

The aminoindanol core as a key scaffold in bifunctional organocatalysts

  • Isaac G. Sonsona,
  • Eugenia Marqués-López and
  • Raquel P. Herrera

Beilstein J. Org. Chem. 2016, 12, 505–523, doi:10.3762/bjoc.12.50

Graphical Abstract
  • derivatization. Thus, in the last decade, it has been widely employed in the field of asymmetric catalysis. Regarding the use of aminoindanol derivatives as ligands in organometallic catalytic complexes, the results have been outstanding. Examples are found in (a) the vanadium-catalyzed asymmetric oxidation of
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Published 14 Mar 2016

Art, auto-mechanics, and supramolecular chemistry. A merging of hobbies and career

  • Eric V. Anslyn

Beilstein J. Org. Chem. 2016, 12, 362–376, doi:10.3762/bjoc.12.40

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  • , and complexity All organic chemists, and in particular supramolecular chemists, must share an enjoyment in creating new chemical entities of our own inspiration. My passion for organic and organometallic synthesis was first developed when performing undergraduate research at the California State
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Published 26 Feb 2016

Enabling technologies and green processes in cyclodextrin chemistry

  • Giancarlo Cravotto,
  • Marina Caporaso,
  • Laszlo Jicsinszky and
  • Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

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  • . The catalytic hydrogenation of 6I-azido-6I-deoxy-β-CD using Pd/C was achieved under US irradiation in MeOH/H2O in 20 min (20.4 kHz, 80 W, yield: 88%); hydrogen was supplied at 1 bar pressure [15]. Sonochemical metals depassivation in organometallic reactions is well established [17]. A typical example
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Published 15 Feb 2016

Versatile deprotonated NHC: C,N-bridged dinuclear iridium and rhodium complexes

  • Albert Poater

Beilstein J. Org. Chem. 2016, 12, 117–124, doi:10.3762/bjoc.12.13

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  • ; iridium; isomerization; N-heterocyclic carbene; rhodium; Introduction In the framework of organometallic chemistry, N-heterocyclic carbenes (NHC) centre a well stablished class of relatively new ligands since in 1991 Arduengo and collaborators isolated the first stable NHC of the imidazole type with
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Published 22 Jan 2016

A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines

  • Tarn C. Johnson and
  • Stephen P. Marsden

Beilstein J. Org. Chem. 2016, 12, 1–4, doi:10.3762/bjoc.12.1

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  • ring, exemplified by approaches to the core of the cyclothiazomycins [9][10]. Regardless of the method employed, these are multistep protocols, frequently employing moisture-sensitive organometallic agents or reducing agents. In this paper, we report a new one-pot, two-component synthesis of 2-(1
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Published 04 Jan 2016

New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand

  • Agnieszka Hryniewicka,
  • Szymon Suchodolski,
  • Agnieszka Wojtkielewicz,
  • Jacek W. Morzycki and
  • Stanisław Witkowski

Beilstein J. Org. Chem. 2015, 11, 2795–2804, doi:10.3762/bjoc.11.300

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  • organometallic compounds were performed using standard Schlenk techniques under an atmosphere of dry argon. CH2Cl2 was dried by distillation over CaH2, toluene over Na. 1,4-Dioxane, ethanol (96%) and trimethyl orthoformate were used as received. Melting points were determined on a Kofler apparatus of the Boetius
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Published 30 Dec 2015

Recent advances in metathesis-derived polymers containing transition metals in the side chain

  • Ileana Dragutan,
  • Valerian Dragutan,
  • Bogdan C. Simionescu,
  • Albert Demonceau and
  • Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

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  • ; Introduction The fast growing interest in metal-containing polymers (metallopolymers) as advanced hybrid materials spurred prolific research in the worldwide organometallic and polymer scientific communities [1][2][3][4]. The variety of metals and the diversity of organic polymers allow tailoring
  • . Information on the physical characteristics of these materials is also included, with a focus on their present and future practical applications. Taking advantage of the considerable reactivity of ring-strained norbornenes and congeners and of their easy functionalization with many organic and organometallic
  • redox-robust triazolylbiferrocenyl (trzBiFc) polymers 4 bearing the organometallic group in the side chain (Scheme 2) [46][47]. Here again, the Grubbs 3rd generation catalyst was very active and highly tolerant towards the biferrocene and triaza functionalities. Noteworthy, the oxidation of the polymer
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Published 28 Dec 2015

Direct estimate of the internal π-donation to the carbene centre within N-heterocyclic carbenes and related molecules

  • Diego M. Andrada,
  • Nicole Holzmann,
  • Thomas Hamadi and
  • Gernot Frenking

Beilstein J. Org. Chem. 2015, 11, 2727–2736, doi:10.3762/bjoc.11.294

Graphical Abstract
  • last two decades, these versatile compounds have been widely employed in transition metal [9][10][11][12][13] and organocatalysis [14][15][16], organometallic [17][18][19] and main group synthesis [20][21][22][23][24][25][26], and activation of small molecules [27][28]. NHCs possess a divalent C(II
  • theoretical approaches can be found in the literature where natural bond orbital calculations (NBO) and energy decomposition analysis (EDA) have been applied to a broad variety of organometallic complexes [35][67][68][69][70][71][72]. Although all the procedures have proven to be a convenient way to evaluate
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Published 24 Dec 2015

Carbon–carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations

  • Tsuyuka Sugiishi,
  • Hideki Amii,
  • Kohsuke Aikawa and
  • Koichi Mikami

Beilstein J. Org. Chem. 2015, 11, 2661–2670, doi:10.3762/bjoc.11.286

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  • perfluoroalkyl organometallic reagents (CnF2n+1M) with high reactivity, act as prominent cross-coupling participants in aromatic perfluoroalkylation reactions [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32]. In order to prepare CnF2n+1Cu species, several
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Published 18 Dec 2015

Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-MIC ligand. Study of the electronic properties and catalytic activities

  • Carmen Mejuto,
  • Beatriz Royo,
  • Gregorio Guisado-Barrios and
  • Eduardo Peris

Beilstein J. Org. Chem. 2015, 11, 2584–2590, doi:10.3762/bjoc.11.278

Graphical Abstract
  • assemblies that include molecular squares and triangles [1][2][3][4][5][6], cylinder-like structures [7][8][9][10][11][12][13], organometallic polymers [14][15][16][17][18][19][20][21][22] and even organometallic mesoporous materials [21][22]. Another interesting feature of this special type of poly-NHCs is
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Published 14 Dec 2015

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

  • Zhan-Jiang Zheng,
  • Ding Wang,
  • Zheng Xu and
  • Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

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  • dialkyne spacers In the past years, bistriazoles with dialkyne spacers have gained significant attention for their potential application in supramolecular chemistry, pharmaceutical chemistry, biological chemistry and organometallic chemistry. The construction of bistriazoles from dialkynes is now well
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Published 11 Dec 2015

Comparison of the catalytic activity for the Suzuki–Miyaura reaction of (η5-Cp)Pd(IPr)Cl with (η3-cinnamyl)Pd(IPr)(Cl) and (η3-1-t-Bu-indenyl)Pd(IPr)(Cl)

  • Patrick R. Melvin,
  • Nilay Hazari,
  • Hannah M. C. Lant,
  • Ian L. Peczak and
  • Hemali P. Shah

Beilstein J. Org. Chem. 2015, 11, 2476–2486, doi:10.3762/bjoc.11.269

Graphical Abstract
  • [15]. In particular, precatalysts based on the (η3-1-t-Bu-indenyl)Pd(L)(Cl) scaffold were highly active because Pd(I) dimer formation was effectively suppressed and the rate of reduction from Pd(II) to Pd(0) was increased [16]. In organometallic chemistry, allyl and indenyl ligands are considered to
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Published 08 Dec 2015

N-Heterocyclic carbenes

  • Steven P. Nolan

Beilstein J. Org. Chem. 2015, 11, 2474–2475, doi:10.3762/bjoc.11.268

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  • Steven P. Nolan Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia 10.3762/bjoc.11.268 The N-heterocyclic carbenes (NHC) now hold a preferred-ligand status in organic and organometallic chemistry. Their role in catalysis continues to grow. When the
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Published 07 Dec 2015

Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates

  • Takamichi Wakamatsu,
  • Kazunori Nagao,
  • Hirohisa Ohmiya and
  • Masaya Sawamura

Beilstein J. Org. Chem. 2015, 11, 2444–2450, doi:10.3762/bjoc.11.265

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  • . Keywords: alkylborane; alkynoate; conjugate addition; copper; multisubstituted alkene; Introduction Copper-mediated conjugate additions of organometallic reagents to alkynoates are powerful tools for the synthesis of multisubstituted alkenes [1][2][3][4][5][6][7][8]. Because of their broad availability
  • and their compatibility with a multitude of functional groups, organoboron compounds are especially popular organometallic reagents. Recently, Yamamoto and co-workers developed copper-catalyzed conjugate additions of aryl- and allylboron compounds to alkynoates [9][10], but alkylboron compounds have
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Published 04 Dec 2015

Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

  • Thibault E. Schmid,
  • Sammy Drissi-Amraoui,
  • Christophe Crévisy,
  • Olivier Baslé and
  • Marc Mauduit

Beilstein J. Org. Chem. 2015, 11, 2418–2434, doi:10.3762/bjoc.11.263

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  • control of the regio- and enantioselectivity of the addition. The aim of this review is to report recent breakthroughs achieved in this challenging field. Keywords: conjugate additions; electron-deficient alkenes; enantioselective catalysis; extended Michael acceptors; organometallic nucleophiles
  • provided dramatic breakthroughs during the last two decades. This review aims to describe the early examples and recent advances in copper-catalyzed asymmetric conjugate additions of organometallic reagents to extended Michael acceptors. First, seminal reports dealing with the reactivity of extended
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Published 03 Dec 2015

Copper-catalyzed arylation of alkyl halides with arylaluminum reagents

  • Bijay Shrestha and
  • Ramesh Giri

Beilstein J. Org. Chem. 2015, 11, 2400–2407, doi:10.3762/bjoc.11.261

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  • catalyzed by Pd and Ni, exploit a wide range of organometallic reagents of Mg, Zr, Zn, Sn, Al, B, Si and In as sources of nucleophiles. Among these metals/non-metals, Al offers a unique feature due to its high chemoselectivity and Lewis acidity [10][11][12]. In addition, Al also has low toxicity and is an
  • inexpensive and earth-abundant metal. Organoaluminum reagents can be prepared directly from metallic aluminum [13][14][15], which further highlights the potential scope of these reagents in organic synthesis. However, despite extensive investigations and applications of organometallic reagents of Si, B, Mg
  • , Zn and Sn in cross-coupling, the utility of organometallic complexes of Al are limited [13][14][16][17][18][19][20][21]. In many cases, direct transmetalation of organoalanes to Pd are sluggish and require ZnCl2 or CdCl2 to facilitate reactions through sequential transmetalations [19]. In some cases
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Published 02 Dec 2015

Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors

  • Morgan Hans,
  • Jan Lorkowski,
  • Albert Demonceau and
  • Lionel Delaude

Beilstein J. Org. Chem. 2015, 11, 2318–2325, doi:10.3762/bjoc.11.252

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  • ], but also for lanthanides and actinides [11][12], as well as for main group elements [12][13]. Countless applications in homogeneous catalysis have already taken advantage of the remarkable stereoelectronic properties and structural diversity of these organometallic species [14][15][16][17]. To give
  • analogues. It turned out, however, to be highly hygroscopic, which hindered its purification and subsequent reactions with moisture-sensitive bases or organometallic compounds. Other counterions were found to alleviate this tendency. In particular, the replacement of HCl with aqueous HBF4 in the original
  • to the large community of organic and organometallic chemists working with NHCs. Structures of the imidazolium and imidazolinium salts discussed in this study and their acronyms. Various synthetic paths leading to the formation of NHCs. Retrosynthetic path for the preparation of symmetrical
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Published 25 Nov 2015

Coupling of α,α-difluoro-substituted organozinc reagents with 1-bromoalkynes

  • Artem A. Zemtsov,
  • Alexander D. Volodin,
  • Vitalij V. Levin,
  • Marina I. Struchkova and
  • Alexander D. Dilman

Beilstein J. Org. Chem. 2015, 11, 2145–2149, doi:10.3762/bjoc.11.231

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  • nitrostryrenes (with the NO2 serving as a leaving group) [20], were employed. Herein, we report that 1-bromoalkynes, which are known to be involved in reactions with various organometallic compounds [22][23][24][25][26][27], can be used as suitable coupling partners for difluorinated organozinc compounds 2. This
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Published 10 Nov 2015

Ru complexes of Hoveyda–Grubbs type immobilized on lamellar zeolites: activity in olefin metathesis reactions

  • Hynek Balcar,
  • Naděžda Žilková,
  • Martin Kubů,
  • Michal Mazur,
  • Zdeněk Bastl and
  • Jiří Čejka

Beilstein J. Org. Chem. 2015, 11, 2087–2096, doi:10.3762/bjoc.11.225

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  • ), with large BET areas and pore volumes, proved to be very suitable supports, due to easy attachment of bulky organometallic complexes onto silica surface ensuring rapid diffusion of reactants to the active catalytic sites [5][6][7][8][9][10][11][12]. Several strategies of immobilization have been
  • ] and such zeolites offer the possibility of their modifications with organometallic moieties in a similar way as mesoporous molecular sieves. Limbach et al. [20] used MWW material as a support for Ru heterogeneous catalyst for cyclooctene oligomerization, however, its activity was rather low. In this
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Published 04 Nov 2015

Hexacoordinate Ru-based olefin metathesis catalysts with pH-responsive N-heterocyclic carbene (NHC) and N-donor ligands for ROMP reactions in non-aqueous, aqueous and emulsion conditions

  • Shawna L. Balof,
  • K. Owen Nix,
  • Matthew S. Olliff,
  • Sarah E. Roessler,
  • Arpita Saha,
  • Kevin B. Müller,
  • Ulrich Behrens,
  • Edward J. Valente and
  • Hans-Jörg Schanz

Beilstein J. Org. Chem. 2015, 11, 1960–1972, doi:10.3762/bjoc.11.212

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  • General procedures All experiments with organometallic compounds were performed under a dry nitrogen atmosphere using standard Schlenk techniques or in an MBraun drybox (O2 < 2 ppm). NMR spectra were recorded with a Varian Inova instrument (300.1 MHz for 1H, 75.9 MHz for 13C, and 121.4 MHz for 31P) and an
  • from commercial sources, and they were degassed and stored in the dry-box when directly used in combination with organometallic complexes, and otherwise were used without further purification. H2ITap∙HCl, complex 8, as well as DEDAM and DAMA were synthesized according to literature procedures [61][71
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Published 21 Oct 2015

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

  • Louis P. Sandjo,
  • Victor Kuete and
  • Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

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  • successfully performed in six steps with an overall yield of 6.5%. The steps included an organometallic intermediate and a Negishi cross-coupling reaction characterized by a transmetalation with zinc and palladium. The benzonaphthyridinone product was transformed into a bromobenzonaphthyridine intermediate by
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Published 18 Sep 2015

A facile synthetic route to benzimidazolium salts bearing bulky aromatic N-substituents

  • Gabriele Grieco,
  • Olivier Blacque and
  • Heinz Berke

Beilstein J. Org. Chem. 2015, 11, 1656–1666, doi:10.3762/bjoc.11.182

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  • : benzimidazolium salts; bulky ligands; cyclization; ligand design; N-heterocyclic carbenes (NHC); ring formation; Introduction Imidazole-based N-heterocyclic carbenes (NHCs) are stable systems serving as ancillary ligands mainly to construct organometallic complexes. These NHCs are sterically and electronically
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Published 17 Sep 2015
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