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Search for "difluoro-" in Full Text gives 107 result(s) in Beilstein Journal of Organic Chemistry.

(2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues

  • Armin de Meijere,
  • Sergei I. Kozhushkov,
  • Dmitrii S. Yufit,
  • Christian Grosse,
  • Marcel Kaiser and
  • Vitaly A. Raev

Beilstein J. Org. Chem. 2014, 10, 2844–2857, doi:10.3762/bjoc.10.302

Graphical Abstract
  • %, respectively). In the case of monofluoro derivative 14c the main product (38%) was trans-(2-methylcyclopropyl)methanol. In the case of the difluoro compound 14b, a mixture of the mono- (25c) and difluoromethylcyclopropylmethanol 25b along with the non-fluorinated alcohol was obtained in a ratio of
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Published 03 Dec 2014

Synthesis and properties of novel star-shaped oligofluorene conjugated systems with BODIPY cores

  • Clara Orofino-Pena,
  • Diego Cortizo-Lacalle,
  • Joseph Cameron,
  • Muhammad T. Sajjad,
  • Pavlos P. Manousiadis,
  • Neil J. Findlay,
  • Alexander L. Kanibolotsky,
  • Dimali Amarasinghe,
  • Peter J. Skabara,
  • Tell Tuttle,
  • Graham A. Turnbull and
  • Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2704–2714, doi:10.3762/bjoc.10.285

Graphical Abstract
  • these two families were studied in order to determine their suitability as emissive materials in photonic applications. Keywords: absorption spectroscopy; BODIPY; cyclic voltammetry; photoluminescence; star-shaped oligofluorene; Introduction The boron-dipyrromethene (BODIPY) or 4,4-difluoro-4-bora-3a
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Published 19 Nov 2014

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

  • Diego Cortizo-Lacalle,
  • Calvyn T. Howells,
  • Upendra K. Pandey,
  • Joseph Cameron,
  • Neil J. Findlay,
  • Anto Regis Inigo,
  • Tell Tuttle,
  • Peter J. Skabara and
  • Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

Graphical Abstract
  • Physics & Astronomy, University of St. Andrews, St. Andrews, KY16 9SS, UK Interdisciplinary Centre for Energy Research, Indian Institute of Science, Bangalore 560012, India 10.3762/bjoc.10.283 Abstract Two novel triads based on a diketopyrrolopyrrole (DPP) central core and two 4,4-difluoro-4-bora-3a,4a
  • % when combined with poly(3-hexylthiophene) [30][31]. 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY, 2), and its derivatives have been widely used in the last two decades due to their outstanding chemical and optoelectronic properties [32][33][34]. BODIPY derivatives are promising compounds to be
  • ], and 7 [47] were prepared according to the literature. 10,10'-(5',5'''-(2,5-Bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis([2,2'-bithiophene]-5',5-diyl))bis(2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide) (9
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Published 18 Nov 2014

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

  • Thilo Focken and
  • Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

Graphical Abstract
  • inhibitors with nanomolar potency against PTP1B [110][111]. Taylor and co-workers were interested to study α-monofluoroalkylphosphonic acids as PTP1B inhibitors in comparison to their difluoro analogues and compounds 16a,b and 132,133 were chosen as model PTP1B inhibitors [68]. The enantiopure α
  • 3500 µM for S-16a and S-16b, respectively), but 10-fold less potent than the difluoro analogues 132 and 133 (IC50 71 µM and 33 µM, respectively). The inhibition studies indicated that the pro-S fluorine in difluoro inhibitors 132 and 133 is essential for good inhibition, although the pro-R fluorine
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Published 13 Aug 2014

Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp2)–H activation/C–O formation

  • Seohyun Shin,
  • Dongjin Kang,
  • Woo Hyung Jeon and
  • Phil Ho Lee

Beilstein J. Org. Chem. 2014, 10, 1220–1227, doi:10.3762/bjoc.10.120

Graphical Abstract
  • , difluoro, or ethoxycarbonyl group failed. Next, the Pd-catalyzed oxidative cyclization of 2-(aryl)arylphosphonic acid monoethyl esters 3 were examined to demonstrate the efficiency of the present method (Scheme 5). 4-Methylphenylphosphonic acid monoethyl esters 3a and 3b with a 3-methyl- and 3,4
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Published 23 May 2014

Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones

  • Murat Kucukdisli,
  • Dorota Ferenc,
  • Marcel Heinz,
  • Christine Wiebe and
  • Till Opatz

Beilstein J. Org. Chem. 2014, 10, 466–470, doi:10.3762/bjoc.10.44

Graphical Abstract
  • class comprises important starting materials for the preparation of the BODIPY dyes (4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes) [37][38] as well as their aza-analogues [39], the 4,4-difluoro-4-bora-3a,4a,8-triaza-s-indacenes. Various methods to prepare 2,4-disubstituted pyrroles have been described in
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Published 24 Feb 2014

Aminofluorination of 2-alkynylanilines: a Au-catalyzed entry to fluorinated indoles

  • Antonio Arcadi,
  • Emanuela Pietropaolo,
  • Antonello Alvino and
  • Véronique Michelet

Beilstein J. Org. Chem. 2014, 10, 449–458, doi:10.3762/bjoc.10.42

Graphical Abstract
  • access to 3,3-difluoro-2-aryl-3H-indoles and 3-fluoro-2-arylindoles are described. An unprecedented aminoauration/oxidation/fluorination cascade reaction of 2-alkynylanilines bearing a linear alkyl group on the terminal triple bond is reported. Keywords: 2-alkynylanilines; fluorination; gold catalysis
  • of 3,3-difluoro-2-oxindoles to give the corresponding 3,3-difluoroindoines when electron-withdrawing groups were present as substituents in the benzene nucleus. The 3,3-difluoro-2-oxindoles were prepared by the reaction of appropriately substituted isatin derivatives with DAST [18]. Anodic
  • fluorination of various N-acetyl-3-substituted indoles was successfully carried out to provide trans-2,3-difluoro-2,3-dihydroindoles which upon treatment with a base gave monofluoroindole derivatives or monofluoro-3H-indoles depending on the substituents at the 3-position [19]. More recently, the indole ring
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Published 20 Feb 2014

Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine

  • Fei Wang,
  • Lingchun Li,
  • Chuanfa Ni and
  • Jinbo Hu

Beilstein J. Org. Chem. 2014, 10, 344–351, doi:10.3762/bjoc.10.32

Graphical Abstract
  • examples include using bis(trifluoromethyl)mercury (Hg(CF3)2) under the promotion of NaI (Scheme 1, reaction 3) [24] and using methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA) under the promotion of KI (Scheme 1, reaction 4) [25]. Our group has focused on the development and application of new
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Published 06 Feb 2014

One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

  • Santos Fustero,
  • Paula Bello,
  • Javier Miró,
  • María Sánchez-Roselló,
  • Günter Haufe and
  • Carlos del Pozo

Beilstein J. Org. Chem. 2013, 9, 2688–2695, doi:10.3762/bjoc.9.305

Graphical Abstract
  • has been the subject of intense research, and efficient methodologies to access these derivatives have been devised [19][20]. However, the analogues bearing the gem-difluoro moiety next to unsaturated bonds have not received comparable attention, probably due to the limited availability of the
  • starting materials. In this context, the recent introduction of difluoropropargyl bromide as fluorinated building block gave access to a wide variety of gem-difluoro-containing alkyne derivatives [21][22]. Recently, we have employed these fluorinated triple bond scaffolds in several types of cyclization
  • -difluoro moiety in an efficient manner. However, at this point it is important to mention that when the 1,7-octadiene protocol was applied using maleic anhydride or 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione as dienophiles (Table 1, method B, entries 1, 6 and 9), a complex mixture was obtained. This is
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Published 28 Nov 2013

Recent advances in transition metal-catalyzed Csp2-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

  • Grégory Landelle,
  • Armen Panossian,
  • Sergiy Pazenok,
  • Jean-Pierre Vors and
  • Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

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Published 15 Nov 2013

Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

  • Ju Hee Kim,
  • Su Jeong Choi and
  • In Howa Jeong

Beilstein J. Org. Chem. 2013, 9, 2470–2475, doi:10.3762/bjoc.9.286

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  • Ju Hee Kim Su Jeong Choi In Howa Jeong Department of Chemistry & Medical Chemistry, Yonsei University, 1 Yonseidae-gil, Wonju, Gangwondo 220-710, Republic of Korea 10.3762/bjoc.9.286 Abstract The cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate (2) with 2 equiv of boronic acids in
  • yields. Unsymmetrical di-coupled products 4 were obtained in high yields from the reactions of 3 with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3. Keywords: boronic acids; cross-coupling reaction; 1,1-diaryl-2,2-difluoroethene; 1,1-difluoro-1,3-dienes; 2,2
  • -difluoro-1-iodoethenyl tosylate; organo-fluorine; Introduction The synthesis of 2,2-disubstituted-1,1-difluoroethenes have received much attention to synthetic organofluorine chemists in recent years because of their unique chemical reactivities toward nucleophiles to produce monofluorinated organic
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Published 14 Nov 2013

Synthesis of enones, pyrazolines and pyrrolines with gem-difluoroalkyl side chains

  • Assaad Nasr El Dine,
  • Ali Khalaf,
  • Danielle Grée,
  • Olivier Tasseau,
  • Fares Fares,
  • Nada Jaber,
  • Philippe Lesot,
  • Ali Hachem and
  • René Grée

Beilstein J. Org. Chem. 2013, 9, 1943–1948, doi:10.3762/bjoc.9.230

Graphical Abstract
  • bearing a CF3 group on the triple bond could be isomerised to the corresponding enones. In that case, Et3N proved to be sufficient as a catalyst to perform this transformation [28]. The required starting propargylic alcohols were obtained by a reaction of the lithium salt of easily available gem-difluoro
  • propargylic derivative 1 [18] with aromatic aldehydes, affording compounds 2a–2e in 71–82% yields (Scheme 2 and Table 1). With these gem-difluoro intermediates, Et3N was not an efficient catalyst since only a low conversion was observed and the reaction was not clean. On the contrary, the DBU-mediated
  • used for the preparation of chemical libraries. Strategy towards the target molecules. Synthesis of enones with a gem-difluoroalkyl side chain. Synthesis of pyrazolines with a gem-difluoro side chain. One-pot synthesis of pyrazolines with a gem-difluoro side chain. Synthesis of pyrrolines with a gem
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Published 26 Sep 2013

Cyclization of substitued 2-(2-fluorophenylazo)azines to azino[1,2-c]benzo[d][1,2,4]triazinium derivatives

  • Aleksandra Jankowiak,
  • Emilia Obijalska and
  • Piotr Kaszynski

Beilstein J. Org. Chem. 2013, 9, 1873–1880, doi:10.3762/bjoc.9.219

Graphical Abstract
  • ); anal. calcd for C19H16FN3O3S: C, 59.21; H, 4.18; N, 10.90; found: C, 58.92; H, 4.09; N, 10.95. 7,9-Difluoro-3-methylpyrido[2,1-c][1,2,4]benzotriazin-11-ium chloride (1d): Method B, yield 40–80% (based on NMR): 1H NMR (300 MHz, CD3CN) δ 2.98 (s, 3H), 7.99 (t, J = 8.1 Hz, 1H), 8.49 (d, J = 5.5 Hz, 1H
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Published 16 Sep 2013

Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates

  • Loránd Kiss,
  • Melinda Nonn,
  • Reijo Sillanpää,
  • Santos Fustero and
  • Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1164–1169, doi:10.3762/bjoc.9.130

Graphical Abstract
  • position 4 was efficiently synthesized. Oxidation of the hydroxy group of amino ester 5 with pyridinium chlorochromate (PCC) in CH2Cl2 yielded the corresponding oxo-group-containing amino ester 8, which was then converted with Deoxo-Fluor in CH2Cl2 at 0 °C to the corresponding geminal difluoro amino ester
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Published 17 Jun 2013

High-spin intermediates of the photolysis of 2,4,6-triazido-3-chloro-5-fluoropyridine

  • Sergei V. Chapyshev,
  • Denis V. Korchagin,
  • Patrik Neuhaus and
  • Wolfram Sander

Beilstein J. Org. Chem. 2013, 9, 733–742, doi:10.3762/bjoc.9.83

Graphical Abstract
  • previous studies of dinitrenes 5a–c [29][30][31], the quintet molecule with DQ = 0.215 cm−1 and EQ = 0.0545 cm−1 can safely be assigned to dinitrene 15 with Θ = 115.7°. Thus, for instance, quintet dinitrene 5a showed DQ = 0.202 cm−1 and EQ = 0.0554 cm−1 [30], and its difluoro-derivative 5b displayed DQ
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Published 16 Apr 2013

Exploring chemical diversity via a modular reaction pairing strategy

  • Joanna K. Loh,
  • Sun Young Yoon,
  • Thiwanka B. Samarakoon,
  • Alan Rolfe,
  • Patrick Porubsky,
  • Benjamin Neuenswander,
  • Gerald H. Lushington and
  • Paul R. Hanson

Beilstein J. Org. Chem. 2012, 8, 1293–1302, doi:10.3762/bjoc.8.147

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  • ], utilizing 3-hydroxypyrrolidine in combination with 2,4-difluoro- and 2,6-difluorobenzenesulfonyl chloride. The nonbridged scaffolds were also prepared as reported previously by a sulfonylation intermolecular Mitsunobu alkylation/intramolecular SNAr protocol [32]. 2,4-Difluoro- and 2,6
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Published 15 Aug 2012

Synthetic glycopeptides and glycoproteins with applications in biological research

  • Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

Graphical Abstract
  • T-antigen, or a difluoro-T-antigen on different positions in the tandem repeat (6–10), showed that high antibody titers were induced in almost all of the immunized mice. Evaluation of the generated antibodies provided evidence that specific immune responses were elicited towards the MUC1 antigens
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Published 30 May 2012

Enantioselective supramolecular devices in the gas phase. Resorcin[4]arene as a model system

  • Caterina Fraschetti,
  • Matthias C. Letzel,
  • Antonello Filippi,
  • Maurizio Speranza and
  • Jochen Mattay

Beilstein J. Org. Chem. 2012, 8, 539–550, doi:10.3762/bjoc.8.62

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  • ’-deoxycytidine dC, cytidine, Cy, cytarabine CT, an epimer of cytidine, and gemcitabine GC, which is the gem-difluoro derivative of 2’-deoxycytidine (Figure 8). Two reaction products were observed in the reaction with the enantiomers (2)-aminobutane: the addition [M·H·G·B]+ and the ligand-exchange [M·H·B
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Published 12 Apr 2012
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  • in good to high yields at 120 °C (bath temperature). It was observed that the start of the exothermic reaction of halogenated 2f was significantly delayed compared to that of unsubstituted 2a. p-Methyl-2b reacted with ZnF2 at 90 °C (run 2). p-Nitro-2i and 2,6-difluoro-2k required a high temperature
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Published 29 Mar 2012

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
  • reagent (3,3-dimethyl-2,3-dihydro-1,2-benzothiazole-1,1-dioxide) [86][87]; p-TsN(F)Me [88]; NFColl = N-fluorocollidinium tetrafluoroborate and NFPy = N-fluoropyridinium tetrafluoroborate [72][89]; F2-bipy = 1,1'-difluoro-bipyridinium bis(tetrafluoroborate) [90]. 1H NMR spectra of a species of the type A
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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
  • summarized in Table 1. The reaction of 1a in the presence of commercially available Ph3PAuCl (5 mol %) and Selectfluor (1.1 equiv) in acetonitrile at rt afforded an inseparable mixture of pyrrolidines 3a in 75% yield and 4a in 17% yield (Table 1, entry 1). Difluoro derivative 4a was isolated as a single
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Published 07 Oct 2011

Novel synthesis of pseudopeptides bearing a difluoromethyl group by Ugi reaction and desulfanylation

  • Jingjing Wu,
  • Hui Li and
  • Song Cao

Beilstein J. Org. Chem. 2011, 7, 1070–1074, doi:10.3762/bjoc.7.123

Graphical Abstract
  • building block 2,2-difluoro-2-(phenylthio)acetic acid (2) as one component, followed by removal of the phenylsulfanyl protecting group in the presence of tributyltin hydride and azobisisobutyronitrile. Keywords: difluoromethyl functionality; gem-difluoromethylene-containing acid; pseudopeptides; reductive
  • functionalized small molecules having a CF2H group [27]. In this work, we first synthesized a protected difluoro-containing building block, 2,2-difluoro-2-(phenylthio)acetic acid (2). The synthesis of compound 2 is illustrated in Scheme 3. The ethyl 2,2-difluoro-2-(phenylthio)acetate (1) was readily prepared by
  • -difluoro-2-(phenylthio)acetic acid (2), followed by the cleavage of the phenylsulfanyl group. Experimental General All reagents were of analytic grade, obtained from commercial suppliers and were used without further purification. Melting points were measured in an open capillary using Büchi melting point
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Published 08 Aug 2011

Heavy atom effects in the Paternò–Büchi reaction of pyrimidine derivatives with 4,4’-disubstituted benzophenones

  • Feng-Feng Kong,
  • Jian-Bo Wang and
  • Qin-Hua Song

Beilstein J. Org. Chem. 2011, 7, 113–118, doi:10.3762/bjoc.7.16

Graphical Abstract
  • (DMT) and 1,3-dimethyluracil (DMU) with benzophenone (1b) and some 4,4’-disubstituted derivatives (dimethoxy (1a), difluoro (1c), dichloro (1d), dibromo (1e) and dicyano benzophenone (1f)) that gives rise to two regioisomeric oxetanes, 2 and 3. The regioselectivity (the ratio of 2/3) decreased
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Published 26 Jan 2011

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

  • Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

Graphical Abstract
  • ) polyhalogenofluoro alkanes as partial fluorinated alkylating agents generates the corresponding sulfides which are appropriate precursors for subsequent conversion to perfluoroalkyl thioethers. For example, α,α-difluoro polyhalogenoalkyl sulfides and α,α-dichlorotrifluoroethyl sulfide can be obtained by reaction of
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Published 18 Aug 2010

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

  • Bruno Linclau,
  • Leo Leung,
  • Jean Nonnenmacher and
  • Graham Tizzard

Beilstein J. Org. Chem. 2010, 6, No. 62, doi:10.3762/bjoc.6.62

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  • Bruno Linclau Leo Leung Jean Nonnenmacher Graham Tizzard School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK 10.3762/bjoc.6.62 Abstract A large-scale synthesis of meso-2,3-difluoro-1,4-butanediol in 5 steps from (Z)-but-2-enediol is described. Crystallographic
  • imaging using 18F [4], and modification of high-performance materials [5]. In recent years, the vicinal difluoride motif has received increasing attention due to the conformational properties instilled by the ‘gauche effect’ [6], which results in the vicinal difluoro gauche conformation being more stable
  • ][33][34]. Herein we describe the first synthesis of meso-2,3-difluoro-1,4-butanediol 3 as a further simple vicinal difluoride building block as well as its successful monosilylation, and our attempts to employ 3 for the synthesis of fluorinated hydrocarbons. Results and Discussion Synthesis The
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Published 08 Jun 2010
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