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

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

  • Anka Utama Putra,
  • Deniz Çakmaz,
  • Nurgül Seferoğlu,
  • Alberto Barsella and
  • Zeynel Seferoğlu

Beilstein J. Org. Chem. 2020, 16, 2282–2296, doi:10.3762/bjoc.16.189

Graphical Abstract
  • approximation is usually used for push-pull organic and organometallic molecules. The results of the EFISH measurements are presented in Table 2. The obtained positive µβ values indicated that the excited states are more polarized than the ground states and that both, the ground and the excited states were
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Published 14 Sep 2020

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

  • Shakeel Alvi and
  • Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

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  • palladium(II) was carried out in the presence of PdCl2(MeCN)2 in a stepwise manner, confirmed by UV–vis spectroscopic technique. The cyclopentadienyl (Cp) ligand has its own identity in the field of organometallic chemistry as a plethora of transition metal complexes contain this moiety in their structures
  • later to this report, in a really dazzling manner, the groups of Rogachev, Hirao, and Petrukhina reported a novel organometallic sandwich supramolecular complex [Na+(18-crown-6)(THF)2][Cs(C21H11‒)2]‒ (138) encapsulating the cesium cation between the sumanenyl anions in a concave manner [69]. To this
  • valuable π-conjugated buckybowl. Four years later, McGlinchey’s group has tried to synthesize it by means of an organometallic precursor but they also did not make available the breakthrough for the research community [70][71]. On the other hand, four years before to the Mehta’s report, Klemm and co
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Published 09 Sep 2020

Efficient [(NHC)Au(NTf2)]-catalyzed hydrohydrazidation of terminal and internal alkynes

  • Maximillian Heidrich and
  • Herbert Plenio

Beilstein J. Org. Chem. 2020, 16, 2080–2086, doi:10.3762/bjoc.16.175

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  • Maximillian Heidrich Herbert Plenio Organometallic Chemistry, Technische Universität Darmstadt, Alarich-Weiss-Str. 12, 64287 Darmstadt, Germany 10.3762/bjoc.16.175 Abstract The efficient hydrohydrazidation of terminal (6a–r, 18 examples, 0.1–0.2 mol % [(NHC)Au(NTf2)], T = 60 °C) and internal
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Published 26 Aug 2020

Pauson–Khand reaction of fluorinated compounds

  • Jorge Escorihuela,
  • Daniel M. Sedgwick,
  • Alberto Llobat,
  • Mercedes Medio-Simón,
  • Pablo Barrio and
  • Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

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  • this sense, while the addition of hard organometallic nucleophiles, such as lithium dialkylcuprates or Grignard reagents, failed, softer nucleophiles such as nitroalkanes cleanly added to the β-position, providing the Michael adduct 61. Unexpectedly, the conjugate addition reaction resulted in
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Published 14 Jul 2020

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

  • Alessandra Del Tito,
  • Havall Othman Abdulla,
  • Davide Ravelli,
  • Stefano Protti and
  • Maurizio Fagnoni

Beilstein J. Org. Chem. 2020, 16, 1476–1488, doi:10.3762/bjoc.16.123

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  • , among the others, the anionic ring-closure of 2-cyanobiaryls by using organometallic reagents [19][20], and an impressive number of transition-metal-catalyzed C(sp2)–C(sp2) cross-coupling processes [21][22][23]. In the last decade, however, photochemical reactions, especially those promoted by a
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Published 25 Jun 2020

In silico rationalisation of selectivity and reactivity in Pd-catalysed C–H activation reactions

  • Liwei Cao,
  • Mikhail Kabeshov,
  • Steven V. Ley and
  • Alexei A. Lapkin

Beilstein J. Org. Chem. 2020, 16, 1465–1475, doi:10.3762/bjoc.16.122

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  • transition metal coordination sphere; the energy of a new M–C bond formed and the thermodynamic stability of organometallic product. With new developments in computational chemistry, mechanistic studies using density functional theory (DFT) provide valuable insights into the reactivity of organometallic
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Published 25 Jun 2020

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

  • Mateo Berton,
  • Kevin Sheehan,
  • Andrea Adamo and
  • D. Tyler McQuade

Beilstein J. Org. Chem. 2020, 16, 1343–1356, doi:10.3762/bjoc.16.115

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  • Abstract Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a
  • fresh organomagnesium reagents on a discovery scale and will do so independent from the operator’s experience in flow and/or organometallic chemistry. Keywords: Knochel–Hauser base; lithium chloride; magnesium; on-demand; packed-bed reactors; plug and flow reactor; synthesizer; turbo Grignard reagent
  • solids without clogging. More recently, we began to think about this combination for producing air- and water-sensitive reagents immediately prior to use. In particular, we were interested in addressing a dichotomy where discovery-scale (50–100 mL) organometallic reagents are used with uncertain
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Published 19 Jun 2020

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

  • Alexander V. Nyuchev,
  • Ting Wan,
  • Borja Cendón,
  • Carlo Sambiagio,
  • Job J. C. Struijs,
  • Michelle Ho,
  • Moisés Gulías,
  • Ying Wang and
  • Timothy Noël

Beilstein J. Org. Chem. 2020, 16, 1305–1312, doi:10.3762/bjoc.16.111

Graphical Abstract
  • recently reported [8][9][11], for example the trifluoromethylation of hydroxyaryls [12][13][14], and the direct introduction of the -OCF3 moiety into an organometallic species [15], a diazo compound [16][17], or an unfunctionalized C–H bond (Scheme 1B). The latter method is particularly interesting
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Published 15 Jun 2020

Oxime radicals: generation, properties and application in organic synthesis

  • Igor B. Krylov,
  • Stanislav A. Paveliev,
  • Alexander S. Budnikov and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

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  • the relatively stable di-tert-butyliminoxyl radical was studied as a reagent in oxidative transformations of various substrates, such as unsaturated hydrocarbons, phenols, amines, and organometallic compounds. A breakthrough in the synthetic use of iminoxyl radicals has occurred in recent years when
  • organolithium reagents 41 at 0 °C in Et2O forming mainly di-tert-butyl oxime 1f and the products of C–O coupling [86]. The reactions were performed by addition of the solution of the organometallic compound 41 in Et2O to the solution of di-tert-butyliminoxyl radical in Et2O. The product yields obtained
  • organolithium reagents. Presumably, the reaction proceeds via SET from the organometallic compound and iminoxyl radical with the formation of an oxime anion and an intermediate C-centered radical. In the case of MeLi and PhLi, which correspond to the most reactive methyl and phenyl radicals, products 44 of
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Published 05 Jun 2020

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

  • Stephanie G. E. Amos,
  • Marion Garreau,
  • Luca Buzzetti and
  • Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

Graphical Abstract
  • the C(sp3) radical, which is intercepted by an organometallic intermediate, obtained by the oxidative addition of a nickel catalyst to the (hetero)aryl bromide 5.2. The desired (hetero)arene product 5.3 is obtained after the reductive elimination of the nickel complex. In this method, the reduced
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Published 29 May 2020

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

  • Esteban P. Urriolabeitia,
  • Pablo Sánchez,
  • Alexandra Pop,
  • Cristian Silvestru,
  • Eduardo Laga,
  • Ana I. Jiménez and
  • Carlos Cativiela

Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

Graphical Abstract
  • Esteban P. Urriolabeitia Pablo Sanchez Alexandra Pop Cristian Silvestru Eduardo Laga Ana I. Jimenez Carlos Cativiela Instituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC - Universidad de Zaragoza), Pedro Cerbuna 12, E-50009 Zaragoza, Spain Supramolecular Organic and Organometallic
  • possibilities: two different competitive C=C bonds amenable to undergo photocycloaddition and at least three different C–H bonds that can be activated by a transition metal provide the potential for a rich organic and organometallic chemistry. Moreover, both the arylidene and the styryl groups can be tuned with
  • of the organometallic core, precipitation of black Pd0 and concomitant formation of the cyclobutanes 5, as represented in Scheme 3. The methoxycarbonylation reaction to give 5 was not as general as the previous steps to give oxazolones 2 or cyclopalladated 3 and 4. In the case of para- or meta-aryl
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Published 25 May 2020

Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F)

  • Louise Ruyet and
  • Tatiana Besset

Beilstein J. Org. Chem. 2020, 16, 1051–1065, doi:10.3762/bjoc.16.92

Graphical Abstract
  • after reduction of the Ruppert–Prakash reagent with sodium borohydride [39]. The key of success was the use of bulky IPr and SIPr ligands to stabilize the organometallic species. Indeed, in the case of IPr as a ligand, the complex was stable in solution at room temperature for at least 24 hours. The
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Published 18 May 2020

Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents

  • Yafei Guo and
  • Syuzanna R. Harutyunyan

Beilstein J. Org. Chem. 2020, 16, 1006–1021, doi:10.3762/bjoc.16.90

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  • Yafei Guo Syuzanna R. Harutyunyan Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands 10.3762/bjoc.16.90 Abstract Copper-catalysed asymmetric C–C bond-forming reactions using organometallic reagents have developed into a powerful tool for
  • organometallic reagents to various acceptors is a useful strategy for C–C bond-forming reactions [1][2][3][4]. These important transformations have been thoroughly developed in the last few decades and were widely used in the synthesis of chiral natural products and bioactive molecules [5][6][7][8]. The majority
  • enantioselectivity have been reported for conjugate additions of both organoaluminium and organozinc reagents, these reagents also present major drawbacks, namely their commercial availability and atom efficiency, given that only one alkyl group is transferred from the organometallic reagent to the Michael acceptor
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Published 14 May 2020

Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas

  • Zhenghui Liu,
  • Peng Wang,
  • Zhenzhong Yan,
  • Suqing Chen,
  • Dongkun Yu,
  • Xinhui Zhao and
  • Tiancheng Mu

Beilstein J. Org. Chem. 2020, 16, 645–656, doi:10.3762/bjoc.16.61

Graphical Abstract
  • friendly and highly effective synthetic methods has been a significant goal of research [1][2][3][4][5]. In this aspect, effective catalytic systems and organometallic chemistry are suitable technologies to accomplish these goals. Carbonylation processes are important transformations in the refinement and
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Published 08 Apr 2020

Aerobic synthesis of N-sulfonylamidines mediated by N-heterocyclic carbene copper(I) catalysts

  • Faïma Lazreg,
  • Marie Vasseur,
  • Alexandra M. Z. Slawin and
  • Catherine S. J. Cazin

Beilstein J. Org. Chem. 2020, 16, 482–491, doi:10.3762/bjoc.16.43

Graphical Abstract
  • in this manner (Scheme 10). The latter was then reacted with tosyl azide. An immediate colour change resulted and based on 1H NMR data, two new species were formed. They were identified as the sulfonyltriazole and an unstable organometallic compound, presumably the triazolylcopper(I) complex C. These
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Published 24 Mar 2020

Recent advances in photocatalyzed reactions using well-defined copper(I) complexes

  • Mingbing Zhong,
  • Xavier Pannecoucke,
  • Philippe Jubault and
  • Thomas Poisson

Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42

Graphical Abstract
  • ; reduction; Introduction For a decade, the realm of catalysis has known a significant renewal with the rise of photocatalysis [1]. The fact that a reaction can be carried out, and, more specifically, catalyzed in the presence of visible light and a photosensitive catalyst (organic or organometallic
  • organic chemistry. Despite the impressive advances reported since the renewal of the field in 2008 [2][3][4], several issues still have to be addressed. Indeed, most of the developed reactions relied on the use of organometallic complexes of expensive noble metals, such as iridium and ruthenium [5]. Even
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Published 23 Mar 2020

Visible-light-induced addition of carboxymethanide to styrene from monochloroacetic acid

  • Kaj M. van Vliet,
  • Nicole S. van Leeuwen,
  • Albert M. Brouwer and
  • Bas de Bruin

Beilstein J. Org. Chem. 2020, 16, 398–408, doi:10.3762/bjoc.16.38

Graphical Abstract
  • form in case of fac-[Ir(ppy)3]), which was proven by mass spectrometry and EPR spectroscopy for one of the catalysts (N,N-5,10-di(2-naphthalene)-5,10-dihydrophenazine) used in this work. The generation of HCl resulting from lactone formation could be an additional problem for organometallic photoredox
  • by the work of Yoon, Stephenson and MacMillan [11]. By selective excitation of an organic or organometallic dye by visible light a species is formed that can act as a single-electron oxidant and single-electron reductant. In this way reactive radical intermediates can be formed catalytically in situ
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Published 16 Mar 2020

Architecture and synthesis of P,N-heterocyclic phosphine ligands

  • Wisdom A. Munzeiwa,
  • Bernard Omondi and
  • Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

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  • , Pietermaritzburg 3201, South Africa 10.3762/bjoc.16.35 Abstract Diverse P,N-phosphine ligands reported to date have performed exceptionally well as auxiliary ligands in organometallic catalysis. Phosphines bearing 2-pyridyl moieties prominently feature in literature as compared to phosphines with five-membered N
  • -heterocyclic phosphines; Introduction Phosphines constitute a large percentage of ligands in organometallic chemistry and over the years, they have received enormous attention. The main interest towards this class of compounds is attributed to aspects such as, the good electron-donating ability of the
  • monitoring and in situ speciation. In addition, phosphine ligands have found various applications as auxiliary ligands in organometallic transition-metal complexes. A great number have exhibited potential application in organic light-emitting devices (OLEDs) [3], medicine [4][5][6] and catalysis [1][7][8
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Published 12 Mar 2020

Formal preparation of regioregular and alternating thiophene–thiophene copolymers bearing different substituents

  • Atsunori Mori,
  • Keisuke Fujita,
  • Chihiro Kubota,
  • Toyoko Suzuki,
  • Kentaro Okano,
  • Takuya Matsumoto,
  • Takashi Nishino and
  • Masaki Horie

Beilstein J. Org. Chem. 2020, 16, 317–324, doi:10.3762/bjoc.16.31

Graphical Abstract
  • to afford the regioregular polythiophene in which 2,5-dihalo-3-substituted thiophene 1 is employed as a monomer precursor, converting to the corresponding organometallic monomer by a halogen−magnesium exchange reaction with a Grignard reagent. The employment of 1 leading to polythiophene has been
  • shown to proceed in a dehalogenative manner [3]. We have recently shown that the generation of the organometallic monomer species can alternatively also be achieved by deprotonation, using 2-halo-3-substituted thiophene 2 or 3 with a bulky magnesium amide Knochel–Hauser base (TMPMgCl⋅LiCl) [7], followed
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Published 05 Mar 2020

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

  • Rafia Siddiqui and
  • Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

Graphical Abstract
  • Figure 2. The most frequently used mechanisms of converting light energy into chemical energy using photoredox catalysts are: (i) photoredox catalysis; (ii) organometallic excitation; (iii) light-induced atom transfer, and (iv) energy transfer. Basically, a photoredox catalyst transforms light energy
  • disappearance of phosphorescence, following the Frank–Condon principle [44][45]. As far as the singlet and triplet excited states of organic dyes and organometallic compounds are concerned, there is a difference in lifetimes. Usually, the lifetime of excited states of organic dyes is nanoseconds, whereas for
  • organometallic compound, the time frame is microseconds. In fact, it has been observed that by virtue of multiple symmetry-allowed and -forbidden electronic transitions, the exact scenario of excited states is highly complex, and thereby offering diverse multiplicities to ground and excited states [46][47][48
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Published 26 Feb 2020

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

  • Delphine Pichon,
  • Jennifer Morvan,
  • Christophe Crévisy and
  • Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

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  • Delphine Pichon Jennifer Morvan Christophe Crevisy Marc Mauduit Université de Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR – UMR 6226, F-35000 Rennes, France 10.3762/bjoc.16.24 Abstract The copper-catalyzed enantioselective conjugate addition (ECA) of organometallic
  • -deficient functions (i.e., aldehydes, thioesters, acylimidazoles, N-acyloxazolidinones, N-acylpyrrolidinones, amides, N-acylpyrroles) were recently investigated. Remarkably, only a few chiral copper-based catalytic systems have successfully achieved the conjugate addition of different organometallic
  • (Michael acceptors) is one of the most relevant and versatile methods to achieve this goal [1][2][3][4]. Among the plethora of metals studied, copper-based catalytic systems proved to be highly efficient for the conjugate addition of various organometallic reagents, such as diorganozinc, triorganoaluminium
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Published 17 Feb 2020

Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions

  • Akihiro Yuasa,
  • Kazunori Nagao and
  • Hirohisa Ohmiya

Beilstein J. Org. Chem. 2020, 16, 185–189, doi:10.3762/bjoc.16.21

Graphical Abstract
  • , agrochemicals and bioactive natural products. Generally, α-alkoxyalkyl anions are presynthesized as stoichiometric organometallic reagents such as organolithium, organozinc, organocuprate, organostannane, organosilane and organoboron compounds [1][2][3][4][5][6]. Alternatively, we showed that easily available
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Published 07 Feb 2020

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

  • Jucleiton J. R. Freitas,
  • Queila P. S. B. Freitas,
  • Silvia R. C. P. Andrade,
  • Juliano C. R. Freitas,
  • Roberta A. Oliveira and
  • Paulo H. Menezes

Beilstein J. Org. Chem. 2020, 16, 168–174, doi:10.3762/bjoc.16.19

Graphical Abstract
  • organometallic species of Cd [16], Ga [17], In [18], Ti [19], Al [20] and Bi [21] were described. However, the majority of these methods involve reagents that are difficult to prepare and to handle due to the sensitivity to air and moisture. The use of less reactive species based on tin [22][23][24], silicon [25
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Published 04 Feb 2020

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

  • Renata Kaczmarek,
  • Dariusz Korczyński,
  • James R. Green and
  • Roman Dembinski

Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

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Published 02 Jan 2020

Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

  • Celine Bittner,
  • Dirk Bockfeld and
  • Matthias Tamm

Beilstein J. Org. Chem. 2019, 15, 2534–2543, doi:10.3762/bjoc.15.246

Graphical Abstract
  • shown for complex I as well [13][16][46]. Beforehand, the promotion of terminal alkyne metathesis (TAM) proved to be difficult due to several deactivation pathways [47][48][49][50][51][52][53]. Regarding the metathesis of organometallic substrates, numerous examples of a conversion via olefin metathesis
  • illustrated for alkyne metathesis reactions of organometallic compounds. After some stoichiometric reactions of ruthenium and rhenium half sandwich complexes [70], several reactions have been described exploiting the reactivity of acetylenic ferrocene compounds [71][72][73][74][75]. For most of these
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Published 24 Oct 2019
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