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

Coordination-driven self-assembly vs dynamic covalent chemistry: versatile methods for the synthesis of molecular metallarectangles

  • Li-Li Ma,
  • Jia-Qin Han,
  • Wei-Guo Jia and
  • Ying-Feng Han

Beilstein J. Org. Chem. 2018, 14, 2027–2034, doi:10.3762/bjoc.14.178

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  • desired tetranuclear metallarectangles were synthesized by using coordination-driven self-assembly of half-sandwich rhodium-based organometallic clip units and organic ligands. The reaction of such an organometallic clip with 4-formylpyridine provided a dinuclear molecular tweezer with pendant aldehyde
  • groups, and subsequent [4 + 4] condensation reactions with diamines provides another route to the target metallarectangles in good yields. The same assemblies can also be easily isolated in one-pot procedures by mixing the organometallic clip, diamines and 4-formylpyridine. Keywords: coordination-driven
  • self-assembly; dynamic covalent chemistry; half-sandwich rhodium complex; metallarectangles; one-pot reaction; supramolecular chemistry; Introduction Over the past two decades, supramolecular structures with organometallic half-sandwich fragments have attracted much attention, including
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Published 03 Aug 2018

Recent advances in materials for organic light emitting diodes

  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2018, 14, 1944–1945, doi:10.3762/bjoc.14.168

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  • in design, from fluorescent compounds to phosphorescent organometallic complexes to organic thermally activated delayed fluorescence (TADF) molecules, the latter driving tremendous recent excitement within the field of organic semiconductor research. This thematic issue of the Beilstein Journal of
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Published 27 Jul 2018

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

  • Xiang Li,
  • Pinhong Chen and
  • Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

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  • Xiang Li Pinhong Chen Guosheng Liu State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China 10.3762/bjoc.14.154 Abstract Hypervalent iodine(III
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Published 18 Jul 2018

Thiocarbonyl-enabled ferrocene C–H nitrogenation by cobalt(III) catalysis: thermal and mechanochemical

  • Santhivardhana Reddy Yetra,
  • Zhigao Shen,
  • Hui Wang and
  • Lutz Ackermann

Beilstein J. Org. Chem. 2018, 14, 1546–1553, doi:10.3762/bjoc.14.131

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  • by weakly-coordinating thiocarbonyl-assisted cobalt catalysis. Thus, carboxylates enabled ferrocene C–H nitrogenations with dioxazolones, featuring ample substrate scope and robust functional group tolerance. Mechanistic studies provided strong support for a facile organometallic C–H activation
  • to a significant H/D scrambling in proximity to the thiocarbonyl group. These findings are indicative of a reversible, thus facile organometallic C–H cobaltation regime (Scheme 4). Next, intermolecular competition experiments revealed that electron-rich arylated thiocarbonylferrocene 1 reacted
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Published 25 Jun 2018

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

  • Cristina Cebrián and
  • Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

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  • organometallic compounds based on heavy transition metal complexes (TMCs) are an appealing research topic of enormous current interest. Amongst all different fields in which they found valuable application, development of emitting materials based on TMCs have become crucial for electroluminescent devices such as
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Published 18 Jun 2018

Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

  • Kimihiro Komeyama,
  • Shunsuke Sakiyama,
  • Kento Iwashita,
  • Itaru Osaka and
  • Ken Takaki

Beilstein J. Org. Chem. 2018, 14, 1413–1420, doi:10.3762/bjoc.14.118

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  • , leading to multi-substituted carbon frameworks (Scheme 1, bottom) [2][3]. The nucleophilic and π-electrophilic organometallic intermediates are used properly in their favorable circumstances. Transmetalation is one of the most vital elemental processes used to drastically change the reactivity of
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Published 11 Jun 2018

Enhanced quantum yields by sterically demanding aryl-substituted β-diketonate ancillary ligands

  • Rebecca Pittkowski and
  • Thomas Strassner

Beilstein J. Org. Chem. 2018, 14, 664–671, doi:10.3762/bjoc.14.54

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  • Rebecca Pittkowski Thomas Strassner Physical Organic Chemistry, Technische Universität Dresden, Bergstraße, 01069 Dresden, Germany 10.3762/bjoc.14.54 Abstract Luminescent organometallic platinum(II) compounds are of interest as phosphors for organic light emitting devices. Their emissive
  • emission properties of organometallic complexes can be tuned by employing different ligand structures. For platinum(II) complexes, the influence of both cyclometalating [21][22][23][24][25][26] and auxiliary ligand [27][28][29][30][31][32] on the emission color as well as their efficiency has been
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Published 21 Mar 2018

Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides

  • Masanori Inaba,
  • Tatsuya Sakai,
  • Shun Shinada,
  • Tsuyuka Sugiishi,
  • Yuta Nishina,
  • Norio Shibata and
  • Hideki Amii

Beilstein J. Org. Chem. 2018, 14, 182–186, doi:10.3762/bjoc.14.12

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  • nucleophilic trifluoromethylation of acid anhydrides to produce γ-hydroxy-γ-trifluoromethyl-γ-butyrolactones, which acted as good precursors in the synthesis of γ-trifluoromethyl-γ-butyrolactones with organometallic reagents [16]. All these protocols involve multiple steps to obtain trifluoromethylphthalides
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Published 19 Jan 2018

Gram-scale preparation of negative-type liquid crystals with a CF2CF2-carbocycle unit via an improved short-step synthetic protocol

  • Tatsuya Kumon,
  • Shohei Hashishita,
  • Takumi Kida,
  • Shigeyuki Yamada,
  • Takashi Ishihara and
  • Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 148–154, doi:10.3762/bjoc.14.10

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  • . The tetrafluorinated multicyclic molecules were successfully obtained in only five or six reaction steps without the need for special handling techniques, as is generally required for thermally unstable organometallic species, representing a reduction of three reaction steps. The improved short-step
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Published 15 Jan 2018
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  • with methylmagnesium bromide [17], and direct methylation using radical reactions [9][18][19]. Hence, we searched for a more viable method for the introduction of the methyl group. A prerequisite was that the organometallic intermediate should be trapped by an electrophile which could later be
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Published 11 Jan 2018

Recent applications of click chemistry for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles

  • Vivek Poonthiyil,
  • Thisbe K. Lindhorst,
  • Vladimir B. Golovko and
  • Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 11–24, doi:10.3762/bjoc.14.2

Graphical Abstract
  • (Scheme 9). Astruc and co-workers have also reported that the use of copper(I) (hexabenzyl)tris(2-aminoethyl)amine bromide ([Cu(I)tren(CH2Ph6)]Br) instead of the CuSO4–ascorbic acid system improves the efficiency of CuAAC for the functionalization of AuNPs with a wide variety of organic, organometallic
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Published 03 Jan 2018

Reactivity of bromoselenophenes in palladium-catalyzed direct arylations

  • Aymen Skhiri,
  • Ridha Ben Salem,
  • Jean-François Soulé and
  • Henri Doucet

Beilstein J. Org. Chem. 2017, 13, 2862–2868, doi:10.3762/bjoc.13.278

Graphical Abstract
  • ][5][6][7][8][9], Suzuki [10][11][12][13][14][15][16][17][18][19], or Kumada [20] couplings [21] (Scheme 1a and b). However, all these procedures require the preparation of an organometallic or a boron derivative of one of the coupling partners, and provide an organometallic salt (MX) as waste. In
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Published 22 Dec 2017

The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones

  • Ommid Anamimoghadam,
  • Saira Mumtaz,
  • Anke Nietsch,
  • Gaetano Saya,
  • Cherie A. Motti,
  • Jun Wang,
  • Peter C. Junk,
  • Ashfaq Mahmood Qureshi and
  • Michael Oelgemöller

Beilstein J. Org. Chem. 2017, 13, 2833–2841, doi:10.3762/bjoc.13.275

Graphical Abstract
  • compound 4, originating from intramolecular nucleophilic substitution, was obtained as a byproduct in 25–30%. Noteworthy, compound 4 is formed as the only product when 1a is treated with organometallic reagents [48][49][50]. When the photoreaction was repeated in a 1:1 mixture of acetone and pH 7 buffer at
  • bond formation (path A), as postulated by Griesbeck et al. for the photocyclization of phthaloyl-L-methionine [58]. Alternatively, the alcoholate obtained after C–C bond formation may cyclize to the oxazolidine (path B), as known from reactions of 1a with organometallic reagents [48][49][50]. When
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Published 20 Dec 2017

Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

  • Matthias Wünsch,
  • David Schröder,
  • Tanja Fröhr,
  • Lisa Teichmann,
  • Sebastian Hedwig,
  • Nils Janson,
  • Clara Belu,
  • Jasmin Simon,
  • Shari Heidemeyer,
  • Philipp Holtkamp,
  • Jens Rudlof,
  • Lennard Klemme,
  • Alessa Hinzmann,
  • Beate Neumann,
  • Hans-Georg Stammler and
  • Norbert Sewald

Beilstein J. Org. Chem. 2017, 13, 2428–2441, doi:10.3762/bjoc.13.240

Graphical Abstract
  • propargylamines by nucleophilic addition. The synthesis of propargylamines by diastereoselective reductive amination requires alkynyl ketones, which are difficult to prepare and are unstable towards reductive conditions. In approach I, organometallic nucleophiles are added to N-sulfinyl propargylimines, derived
  • from aldehydes. According to approach II, a metallated terminal alkyne is added to an N-sulfinylaldimine. In approach I, the organometallic nucleophile is transferring the amino acid side chain, in approach II, the amino acid side chain comes from the aldehyde incorporated in the imine. Results and
  • -butyl sulfinamide led to the enantiomerically pure sulfinylimines 3a and 3b, which were reacted with a variety of organometallic compounds, including iPrMgBr, MeMgBr and BnMgBr. The reaction of the enantiomerically pure N-sulfinylimines 3a and 3b with aliphatic organometallic nucleophiles resulted in
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Published 15 Nov 2017

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

  • Jan Podlesný,
  • Lenka Dokládalová,
  • Oldřich Pytela,
  • Adam Urbanec,
  • Milan Klikar,
  • Numan Almonasy,
  • Tomáš Mikysek,
  • Jaroslav Jedryka,
  • Iwan V. Kityk and
  • Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

Graphical Abstract
  • -photon absorbers (2PA). In this respect, the central DPP bicyclic lactam is often decorated with electron donors such as alkoxy- or dialkylamino groups [11][12], triphenylamine [13][14], heterocyclic carbazole [15], thiophene [16][17], furan [18], and organometallic ferrocene [19]. 2PA-active DPPs were
  • substituent shifts the EHOMO to more positive values, slightly deepened ELUMO, and reduces the ΔE within the order of 1 (dimethylanilino) > 2 (4-methoxyphenyl) > 4 (5-methoxythiophen-2-yl) > 3 (thiophen-2-yl). The organometallic ferrocene in 5b caused reduction of the HOMO–LUMO gap up to 1.47 eV and proved to
  • and 3b/4b) and are not capable to properly calculate organometallic ferrocene derivatives 5b. However, this is its common feature [45][46]. Conclusion In conclusion, we have designed a series of diketopyrrolopyrrole derivatives having D–π–A–π–D arrangement. Nine new chromophores were conveniently and
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Published 08 Nov 2017

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

  • Martina Tireli,
  • Silvija Maračić,
  • Stipe Lukin,
  • Marina Juribašić Kulcsár,
  • Dijana Žilić,
  • Mario Cetina,
  • Ivan Halasz,
  • Silvana Raić-Malić and
  • Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

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  • while monitoring the reaction course by in situ Raman spectroscopy [45]. While this methodology was already successfully applied for establishing mechanistic and kinetic details in the formation of cocrystals [46], coordination and organometallic compounds [47], it proved to be especially valuable for
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Published 06 Nov 2017

Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective

  • Yaroslav D. Boyko,
  • Valentin S. Dorokhov,
  • Alexey Yu. Sukhorukov and
  • Sema L. Ioffe

Beilstein J. Org. Chem. 2017, 13, 2214–2234, doi:10.3762/bjoc.13.220

Graphical Abstract
  • intermediate 45, which was subjected to Wittig olefination. Subsequent aza-Sakurai cyclization of intermediate 46 provided tricyclic derivative 47 as a single stereoisomer, which was then transformed into target myrioneurinol by standard operations. Addition of organometallic reagents to conjugated
  • nitrosoalkenes The addition of organometallic compounds to conjugated nitrosoalkenes is a promising strategy towards various α-branched oximes. Unfortunately, these reactions are not sufficiently developed to date and only few reports dealing with a successful Michael addition of organometallic compounds to α
  • -position and an excess (5 equivalents) of organometallic compound is needed, the reaction is believed to proceed through nitrosoalkene intermediate NSA11. The reaction proved to be efficient yielding the desired β-hydroxyoximes 54 in high yields (80–90%). Interestingly, with cyclohexenone oxime excellent
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Published 23 Oct 2017

Phosphonic acid: preparation and applications

  • Charlotte M. Sevrain,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

Graphical Abstract
  • phosphorus-containing functional groups [2], on specific applications (hybrid materials [3], surface modification [4], oil industry [5]) or dedicated to a family of compounds (e.g., aminophosphonic acids [6], organometallic phosphonic acids [7]). However, no recent review was focused on the different methods
  • develop bone targeting which was assessed for therapy [96] and imaging [97][98]. Finally, the phosphonic acid group was also employed to immobilize organic or organometallic molecules on the surface of metal oxide [99][100] (Al2O3 [101], TiO2 [102][103], SnO2 [104], Fe3O4 [105], ZnO [106]), CdSe quantum
  • dendrimers 67 [192]. The use of BrSiMe3 was also applied to diverse organometallic compounds as exemplified in Figure 20. This procedure was applicable to compounds featuring CpFe(CO)2 68 [193] or ferrocenyl 69 [194][195] moieties but also to palladium or platinium pincer complexes 70 [196] or arene–chrome
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Published 20 Oct 2017

The effect of milling frequency on a mechanochemical organic reaction monitored by in situ Raman spectroscopy

  • Patrick A. Julien,
  • Ivani Malvestiti and
  • Tomislav Friščić

Beilstein J. Org. Chem. 2017, 13, 2160–2168, doi:10.3762/bjoc.13.216

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  • , have emerged as a highly versatile and general route to conduct chemical reactions in the absence of bulk solvents [2]. Indeed, the demonstrated versatility in organic [5][6][7][8], organometallic [9][10], pharmaceutical [11][12], supramolecular [13], metal-organic [14][15], and materials synthesis [16
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Published 18 Oct 2017

Main group mechanochemistry

  • Agota A. Gečiauskaitė and
  • Felipe García

Beilstein J. Org. Chem. 2017, 13, 2068–2077, doi:10.3762/bjoc.13.204

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  • sustainable alternatives to conventional solvent-based synthetic routes. Mechanochemistry has already been successfully applied to the synthesis of active pharmaceutical ingredients (APIs), organic compounds, metal oxides, coordination compounds and organometallic complexes. In the main group arena, examples
  • , and during the last 25 years, mechanochemical methods have been applied to various fields, including catalysis [47], organic synthesis [5][7][48][49], metal-organic frameworks (MOFs) [50][51], coordination [52], organometallic [11], supramolecular [53], environmental [54][55], APIs [56], medicinal [57
  • . In the field of organometallic chemistry, we highlight the large-scale synthesis of SrCp′2(OEt2) (Cp′ = C5Me4(n-Pr)) (1) [82], an ideal precursor for the chemical vapour deposition (CVD) of strontium-based semiconductors – a key material in memory devices [83]. Previously, this compound could only be
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Published 05 Oct 2017

Mechanochemical synthesis of small organic molecules

  • Tapas Kumar Achar,
  • Anima Bose and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

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  • (C–X), etc. is documented. Mechanochemical syntheses of heterocyclic rings, multicomponent reactions and organometallic molecules including their catalytic applications are also highlighted. Keywords: ball-milling; green chemistry; mechanochemistry; solid-phase synthesis; solvent-free synthesis
  • bond formation reactions, multicomponent reactions, heterocyclic ring synthesis, synthesis of organometallic complexes and their catalytic applications, and so on. Review Mechanochemical organic synthesis Famous philosopher Aristotle’s statement “No Coopora nisi Fluida” means ‘no reaction is possible
  • transition metals, could be performed in shorter reaction time and uses stable dichalcogenides rather than toxic thiols and selenols. Organometallic synthesis and catalytic application Mechano-synthesis of organometallic compounds The last decade has witnessed a rapid growth of mechanochemistry in organic
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Published 11 Sep 2017

Solvent-free sonochemistry: Sonochemical organic synthesis in the absence of a liquid medium

  • Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 1850–1856, doi:10.3762/bjoc.13.179

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  • layered materials such as graphite (to form graphene) [10], but it has also been employed in the formation of organometallic [11] and organic compounds [12]. Great success has been found in the treatment of waste water by ultrasonic irradiation, to remove heavy metals or degrade aromatic constituents [13
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Published 04 Sep 2017

Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation

  • Raja Ben Othman,
  • Mickaël J. Fer,
  • Laurent Le Corre,
  • Sandrine Calvet-Vitale and
  • Christine Gravier-Pelletier

Beilstein J. Org. Chem. 2017, 13, 1533–1541, doi:10.3762/bjoc.13.153

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  • organometallic reagents onto nucleoside aldehyde (Table 1), we decided to investigate the influence of the protecting groups of the uridine aldehyde on the stereochemical outcome of the nucleophilic addition of a Grignard reagent and we wish to report herein the results of our study. Results and Discussion We
  • organometallic reagent on nucleoside aldehydes. Influence of the protecting groups and conditions on the diastereoselectivity of the alkynyl Grignard addition on uridine derived aldehydes. Supporting Information Supporting Information File 107: Description of the materials and methods, and the preparation and
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Published 04 Aug 2017

Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

  • M. Fernanda N. N. Carvalho,
  • Rudolf Herrmann and
  • Gabriele Wagner

Beilstein J. Org. Chem. 2017, 13, 1230–1238, doi:10.3762/bjoc.13.122

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  • the addition of organometallic reagents to the camphor carbonyl group allows for selective introduction of additional substituents and functional groups (e.g., as in [7]). Camphor was the source of chirality in Holton’s taxol synthesis [8] and other approaches to the taxane group of compounds [9][10
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Published 26 Jun 2017

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

  • Stephan Scheeff and
  • Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

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  • . Notably, they had to switch the halide/organometallic functionality of each building block after an unsuccessful coupling between the stannane synthesized by reduction and methylation of ketone 67 and the iodine derived from fragment 62. They assume that the steric hindrance of the methyl group in C10
  • already coupled a similar fragment 70 with the southern fragment 57 by an organometallic addition, however, with a lack of stereoselectivity in C23 position [45]. As shown in Scheme 14, they started with the deprotection of the primary TBS ether 70 and DMP oxidation to the aldehyde 71. The bromide 57
  • . Final steps of Trauner’s total synthesis of archazolid B. Overview of the different retrosynthetic approaches for the synthesis of dihydroarchazolid B (3) reported by the O'Neil group. Fragment synthesis of 69 towards the total synthesis of 3. Organometallic addition of the side chain to access free
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Published 07 Jun 2017
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