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Search for "fluorinated compounds" in Full Text gives 42 result(s) in Beilstein Journal of Organic Chemistry.

The use of 4,4,4-trifluorothreonine to stabilize extended peptide structures and mimic β-strands

  • Yaochun Xu,
  • Isabelle Correia,
  • Tap Ha-Duong,
  • Nadjib Kihal,
  • Jean-Louis Soulier,
  • Julia Kaffy,
  • Benoît Crousse,
  • Olivier Lequin and
  • Sandrine Ongeri

Beilstein J. Org. Chem. 2017, 13, 2842–2853, doi:10.3762/bjoc.13.276

Graphical Abstract
  • drugs contain fluorine atoms or fluoroalkyl groups, representing 150 fluorinated molecules, and this trend is expected to increase to about 30% in the early future as a new generation of fluorinated compounds is currently in Phase II−III clinical trials [1]. In parallel, pharmaceutical peptides are
  • a free amine is crucial to establish ionic interactions with acidic residues of Aβ1-42 [15][39][40][41]. No activity was observed at a 1:1 ratio for the fluorinated compounds 3b and 4b, while an increase of the fluorescence plateau was observed in the presence of the Ser and Thr containing compounds
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Published 21 Dec 2017

Electrophilic trifluoromethylselenolation of terminal alkynes with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate

  • Clément Ghiazza,
  • Anis Tlili and
  • Thierry Billard

Beilstein J. Org. Chem. 2017, 13, 2626–2630, doi:10.3762/bjoc.13.260

Graphical Abstract
  • , fluorinated compounds have been the subject of growing interest [1][2]. The specific properties introduced by fluorinated groups have contributed to the “success story” of fluorinated molecules. Nowadays, fluorinated compounds find applications in various fields, from life sciences to materials [3][4][5][6][7
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Published 07 Dec 2017

Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides

  • Tao Fan,
  • Wei-Dong Meng and
  • Xingang Zhang

Beilstein J. Org. Chem. 2017, 13, 2610–2616, doi:10.3762/bjoc.13.258

Graphical Abstract
  • applications of fluorinated compounds in life and materials science, developing efficient and straightforward methods for the synthesis of fluorinated compounds has become more and more important. Although great achievements have been made in the introduction of fluorine atom(s) into organic molecules over the
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Published 06 Dec 2017

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

  • Satoru Mori and
  • Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

Graphical Abstract
  • to metabolism and oxidation compared to non-fluorinated compounds. In addition to their stability, perfluorinated compounds exhibit non-tackiness, low friction, and the ability to repel water and oil [24]. Therefore, they are used as functional materials such as fluorocarbon polymer. Fluorine is also
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Published 27 Oct 2017

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

  • Forrest S. Etheridge,
  • Roshan J. Fernando,
  • Sandra Pejić,
  • Matthias Zeller and
  • Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

Graphical Abstract
  • routinely obtain because they are obtained under similar conditions as the new results with the fluorinated compounds. Zn(L2–L4)2 showed an increase in PCE compared to Zn(WS3)2, due to an increase in JSC. This points to a generally positive effect of fluorination on device performance. The current best
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Published 29 Aug 2016

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

  • Charlotte Collet,
  • Françoise Chrétien,
  • Yves Chapleur and
  • Sandrine Lamandé-Langle

Beilstein J. Org. Chem. 2016, 12, 353–361, doi:10.3762/bjoc.12.39

Graphical Abstract
  • access the fluorinated compounds bearing easily removable acetyl protecting groups (Scheme 5, see Supporting Information File 1 for full experimental data). Starting from the fully hydroxylated inositols myo-3 and scyllo-3, the first step was the protection of the primary hydroxy group with trityl
  • fluorination. The utilization of isopropenyl acetate as solvent in the presence of p-TSA at 80 °C for 2 h [52] gave the corresponding acetylated compounds myo-23 and scyllo-23 in good to excellent yields. The access to fluorinated compounds by nucleophilic substitution was investigated starting from these
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Published 25 Feb 2016

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

Graphical Abstract
  • acid derivatives via carbon–carbon bond cleavage demands a high reaction temperature or basic conditions. Nevertheless, the simplicity of the operation and the reliability of higher yields would help the synthesis of fluorinated compounds in various fields. Trifluoromethylation using trifluoroacetate
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Published 18 Dec 2015

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

  • Svetlana P. Panchenko,
  • Alexei D. Averin,
  • Maksim V. Anokhin,
  • Olga A. Maloshitskaya and
  • Irina P. Beletskaya

Beilstein J. Org. Chem. 2015, 11, 2297–2305, doi:10.3762/bjoc.11.250

Graphical Abstract
  • rather poor yield (Table 3, entries 5 and 6), but the use of the ligand L1 improved the result (Table 3, entry 7). In the case of diamine 4 the yields of the corresponding products 30–32 and 34 were somewhat lower (Table 3, entries 8–11), and with fluorinated compounds we managed to isolate also
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Published 24 Nov 2015

A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

  • Natalia V. Pavlenko,
  • Tatiana I. Oos,
  • Yurii L. Yagupolskii,
  • Igor I. Gerus,
  • Uwe Doeller and
  • Lothar Willms

Beilstein J. Org. Chem. 2014, 10, 722–731, doi:10.3762/bjoc.10.66

Graphical Abstract
  • the GABAB receptor [18]. In light of the above and in connection with our interest in the chemistry of fluorinated compounds of phosphorus we report here the preparation of a series of novel (1-aminoalkyl)phosphinic acids bearing CF3 or CHF2 groups at phosphorus. Results and Discussion Research
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Published 26 Mar 2014

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

  • Gijs Koopmanschap,
  • Eelco Ruijter and
  • Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

Graphical Abstract
  • % CuIP(OEt)3 and phenyl propargyl ether as the alkyne provided triazole-peptidomimetics 85 in 70–80% yield (Scheme 26). In a follow-up publication the same authors reported the development of tetrapeptides bearing α-CF3-α-amino and α-CF3-α-amino phosphonate cores (Scheme 27) [86]. Fluorinated compounds
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Published 04 Mar 2014

Halogenated volatiles from the fungus Geniculosporium and the actinomycete Streptomyces chartreusis

  • Tao Wang,
  • Patrick Rabe,
  • Christian A. Citron and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 2767–2777, doi:10.3762/bjoc.9.311

Graphical Abstract
  • ; organohalogen compounds; volatiles; Introduction Today several thousands of halogenated natural products are known, most of them being produced by marine organisms [1]. The majority of halogenated natural products are chlorinated or brominated, while iodinated and particularly fluorinated compounds are
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Published 03 Dec 2013

A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

  • Raoni S. B. Gonçalves,
  • Michael Dos Santos,
  • Guillaume Bernadat,
  • Danièle Bonnet-Delpon and
  • Benoit Crousse

Beilstein J. Org. Chem. 2013, 9, 2387–2394, doi:10.3762/bjoc.9.275

Graphical Abstract
  • supply a variety of organic functionalities including γ-amino alcohols [12], β-amino acids [13], β-hydroxy ketones [14][15] and β-hydroxy nitriles [14][15]. Fluorinated compounds play a central role in different branches of chemistry [16]. The incorporation of a fluorine atom into bioactive molecules
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Published 07 Nov 2013

Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters

  • Lin Yan,
  • Zhiqiang Han,
  • Bo Zhu,
  • Caiyun Yang,
  • Choon-Hong Tan and
  • Zhiyong Jiang

Beilstein J. Org. Chem. 2013, 9, 1853–1857, doi:10.3762/bjoc.9.216

Graphical Abstract
  • properties, compared with their parent compounds [1]. Due to the rareness of organofluorine compounds in nature, synthetic fluorinated compounds have been widely applied in numerous areas, including materials, agrochemicals, pharmaceuticals and fine chemicals [2][3][4]. In this context, the stereoselective
  • conjugate addition and Mannich reaction of α-fluoro-β-ketoesters with excellent results [38][39][40]. Herein, we wish to report the first allylic alkylation of MBH carbonates with α-fluoro-β-ketoesters in excellent enantioselectivities and moderate diastereoselectivities, furnishing enantiopure fluorinated
  • compounds with chiral quaternary carbon centres containing a fluorine atom. Results and Discussion In the preliminary experiments, we investigated the reaction of α-fluoro-β-ketoester 1a with MBH carbonate 2a as the model substrate, in the presence of several commercially available Cinchona alkaloids as
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Published 11 Sep 2013

Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

  • Lukas Hintermann,
  • Mauro Perseghini and
  • Antonio Togni

Beilstein J. Org. Chem. 2011, 7, 1421–1435, doi:10.3762/bjoc.7.166

Graphical Abstract
  • specifically fluorinated compounds remain difficult to access because of limitations of the synthetic methodology or unpredictable reaction outcomes in the case of fluorinated starting materials. Seebach coined the term “flustrates” for “fluorinated substrates”; a term that also hints at the frustrations
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Published 17 Oct 2011

Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles

  • Antoine Simonneau,
  • Pierre Garcia,
  • Jean-Philippe Goddard,
  • Virginie Mouriès-Mansuy,
  • Max Malacria and
  • Louis Fensterbank

Beilstein J. Org. Chem. 2011, 7, 1379–1386, doi:10.3762/bjoc.7.162

Graphical Abstract
  • catalysis; Selectfluor; Introduction The useful properties of fluorinated compounds in medicinal chemistry have motivated an intense effort towards the synthesis of new molecules bearing fluorine substituents [1][2]. Therefore, the development of a rapid access to C–F bonds is of great importance. Quite
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Published 07 Oct 2011

Preparation, structures and preliminary host–guest studies of fluorinated syn-bis-quinoxaline molecular tweezers

  • Markus Etzkorn,
  • Jacob C. Timmerman,
  • Matthew D. Brooker,
  • Xin Yu and
  • Michael Gerken

Beilstein J. Org. Chem. 2010, 6, No. 39, doi:10.3762/bjoc.6.39

Graphical Abstract
  • -phenylenediamine (guest [red]); host concentration: 0.01M; host–guest ratio: 1:2 (1), 1:5 (2), 1:10 (3), 1:20 (4). Fluorinated molecular tweezers. Synthesis of non-fluorinated and fluorinated syn-bis-quinoxalines. Crystallographic details for 16c and related non-fluorinated compounds. Supporting Information
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Preliminary Communication
Published 20 Apr 2010

Trifluoromethyl ethers – synthesis and properties of an unusual substituent

  • Frédéric R. Leroux,
  • Baptiste Manteau,
  • Jean-Pierre Vors and
  • Sergiy Pazenok

Beilstein J. Org. Chem. 2008, 4, No. 13, doi:10.3762/bjoc.4.13

Graphical Abstract
  • of the 31 new chemical entities approved in 2002 contain one or several fluorine atoms. According to the World Drug Index (WDI), there are 128 fluorinated compounds with US trade names. Even more fluorinated drugs are predicted to be developed in the near future, as fluoro-organic compounds continue
  • ) Thifluzamide as well as the inhibitor of acetolactate synthase (ALS) Flucarbazone-sodium. It was estimated that the number of fluorinated compounds currently under development represent some 35–50% of the all active ingredients under development [2]. One or several fluorine atoms as substituents at specific
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Published 29 Apr 2008
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