Indium-mediated allylation in carbohydrate synthesis: A short and efficient approach towards higher 2-acetamido-2-deoxy sugars

• Christopher Albler,
• Ralph Hollaus,
• Hanspeter Kählig and
• Walther Schmid

Beilstein J. Org. Chem. 2014, 10, 2230–2234, doi:10.3762/bjoc.10.231

• makes use of readily accessible pentoses and hexoses, which are subjected to indium-mediated two-carbon chain elongation. Subsequent ozonolysis and treatment with base yields α,β-unsaturated aldehydes, which are stereoselectively epoxidized using Jørgenson’s protocol. After Wittig chain elongation the

• azide reduction followed by final deacetylation using methanolic sodium methoxide furnishes the title compounds. Keywords: allylation; carbohydrates; epoxidation; indium; multivalent glycosystems; organocatalysis; Introduction The indium-mediated allylation of carbonyl compounds has proven to be a

• allowing for an evaluation of structure–activity relationships. Results and Discussion We started our reaction sequence with an indium-mediated allylation of unprotected carbohydrates using D-arabinose (1a), D-galactose (1b) and D-glucose (1c) as starting materials. The Barbier-type chain elongation

The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

• Aurica Farcas,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert,
• Flavian Farcas,
• Iuliana Stoica and
• Anton Airinei

Beilstein J. Org. Chem. 2014, 10, 2145–2156, doi:10.3762/bjoc.10.222

• , IP and EA compared to any of the constituents, which is necessary for electronic applications. The diagram with HOMO/LUMO levels and the work function of the indium tin oxide (ITO) coated glass substrates with poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) (anode) and Ca or Al

• compounds in addition to the work function of the indium tin oxide (ITO) coated glass substrates with poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) (anode) and Ca or Al (cathode) are available. Supporting Information File 554: Characterization data of the compounds: FTIR, 1H NMR

Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

• Alexander Burkhart and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 1951–1958, doi:10.3762/bjoc.10.203

• measured at room temperature. FTIR spectra were recorded on a Nicolet 6700 FTIR spectrometer equipped with an ATR unit. Differential scanning calorimetry (DSC) was performed using a Mettler Toledo DSC 822 instrument equipped with a sample robot TSO801RO. For calibration, standard tin, indium, and zinc

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

• Maja Kandziora and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

• phenylthio-substituted 1,2-oxazine derivatives [32]. Compound 10 is easily accessible by a mild cleavage of the corresponding acetonide by an indium trichloride-mediated hydrolysis [33]. By using cerium ammonium nitrate as Lewis acid [34] in high concentration (13 mmol/mL) as well as an excess of 1-bromo-4

Synthesis of the B-seco limonoid core scaffold

• Hanna Bruss,
• Hannah Schuster,
• Rémi Martinez,
• Markus Kaiser,
• Andrey P. Antonchick and
• Herbert Waldmann

Beilstein J. Org. Chem. 2014, 10, 194–208, doi:10.3762/bjoc.10.15

• envisaged to be constructed by 1,2-addition, using the free β-hydroxy functionality in 63 as directing group. Several conditions with allyl boronates, stannanes, silanes, indium, magnesium bromide, cerium, zinc bromide and other reagents have been screened. Finally, the best result was achieved with

N,N'-(Hexane-1,6-diyl)bis(4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide): Synthesis via cyclodextrin mediated N-alkylation in aqueous solution and further Prilezhaev epoxidation

• Julian Fischer,
• Simon Millan and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2834–2840, doi:10.3762/bjoc.9.318

• calibration, standard tin, indium, and zinc samples were used. Heating and cooling curves were determined between −30 and 130 °C at a heating rate of 15 °C/min. The Tg value was taken from the inflection point of the second heating curve. Electrospray ionization mass spectrometry (ESIMS) was conducted on a

Oligomeric epoxide–amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

• Julian Fischer and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2803–2811, doi:10.3762/bjoc.9.315

• first three intersections of G’ and G’’ taking initial fluctuations due to homogenization and sheer-thinning processes not into account. Glass transition temperatures (Tg) were determined using a Mettler Toledo DSC 822e equipped with a sample robot TSO801RO. For calibration, standard tin, indium, and

Crystal design using multipolar electrostatic interactions: A concept study for organic electronics

• Peer Kirsch,
• Qiong Tong and
• Harald Untenecker

Beilstein J. Org. Chem. 2013, 9, 2367–2373, doi:10.3762/bjoc.9.272

• system equipped with a 7000A Triple Quad detector. Melting points were determined by differential scanning calorimetry (DSC) performed on a Universal V4.5A (TA Instruments) at a heating/cooling rate of 20 K∙min−1. The temperature was calibrated with indium. The measurements were performed under a

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

• Helga Seyler,
• Jegadesan Subbiah,
• David J. Jones,
• Andrew B. Holmes and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

• following device geometry: ITO/PEDOT:PSS/P3HT:PC61BM (1:1)/ZnO nanoparticle/Al, where ITO = indium tin oxide, PEDOT:PSS = poly(3,4-ethylenedioxy-thiophene):poly(styrenesulfonate) and PC61BM = [6,6]-phenyl-C61-butyric acid methyl ester (Figure 5a). The P3HT:PC61BM active layer was deposited by spin coating

Thermotropic and lyotropic behaviour of new liquid-crystalline materials with different hydrophilic groups: synthesis and mesomorphic properties

• Alexej Bubnov,
• Miroslav Kašpar,
• Věra Hamplová,
• Ute Dawin and
• Frank Giesselmann

Beilstein J. Org. Chem. 2013, 9, 425–436, doi:10.3762/bjoc.9.45

• of the glass plates are covered by indium-tin-oxide electrodes and polyimide layers unidirectionally rubbed, which ensures planar alignment of the molecules, e.g., bookshelf geometry in the smectic phase. In addition, for texture observation on samples with homeotropic alignment, free-standing films

• . The temperature was calibrated from extrapolated onsets of the melting points of water, indium and zinc. The enthalpy change was calibrated based on the enthalpies of melting of water, indium and zinc. The small-angle X-ray scattering studies have been performed with Ni-filtered Cu Kα radiation

The chemistry of bisallenes

• Henning Hopf and
• Georgios Markopoulos

Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225

• bisallene was reported recently [85]. The reaction amounts to a 1,2,4,5-hexatetraenylation of 4-acetoxy-2-azetidinones, such as 111 (Scheme 29). In this case the organoindium reagent, formed in situ from 1,6-dibromo-2,4-hexadiyne (112) and indium, was coupled with 111 in the presence of LiCl in DMF to yield

A new approach toward the total synthesis of (+)-batzellaside B

• Jolanta Wierzejska,
• Shin-ichi Motogoe,
• Yuto Makino,
• Tetsuya Sengoku,
• Masaki Takahashi and
• Hidemi Yoda

Beilstein J. Org. Chem. 2012, 8, 1831–1838, doi:10.3762/bjoc.8.210

• more efficient synthetic method for the stereoselective allylation of 4 using an appropriate combination of allylic reagent and Lewis acid to produce the desired diastereomer 7 preferentially. Beginning with a reaction employing indium chloride (InCl3) instead of TBSOTf at 0 °C in dichloromethane, we

Polysiloxane ionic liquids as good solvents for β-cyclodextrin-polydimethylsiloxane polyrotaxane structures

• Narcisa Marangoci,
• Rodinel Ardeleanu,
• Laura Ursu,
• Constanta Ibanescu,
• Maricel Danu,
• Mariana Pinteala and
• Bogdan C. Simionescu

Beilstein J. Org. Chem. 2012, 8, 1610–1618, doi:10.3762/bjoc.8.184

• 10 °C/min was applied. Nitrogen purge gas was used as an inert atmosphere at a flow rate of 50 mL/min. The apparatus was temperature- and sensitivity-calibrated with indium, according to standard procedures. FTIR spectra FTIR spectra were recorded on a Bruker Vertex 70 FTIR spectrometer from KBr

Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

• Dieter Enders,
• Jeanne Fronert,
• Tom Bisschops and
• Florian Boeck

Beilstein J. Org. Chem. 2012, 8, 1112–1117, doi:10.3762/bjoc.8.123

• (2-hydroxyphenyl)propiolate 20 could be reduced to the corresponding ortho-hydroxy-(Z)-cinnamate, which ring closed immediately to coumarin 21. Deprotection of the acetonide under acidic conditions proved to be difficult due to the acid labile nature of the 1,3-diol. However, indium(III) catalysis in

Multistep organic synthesis of modular photosystems

• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2012, 8, 897–904, doi:10.3762/bjoc.8.102

• sophisticated, probably as sophisticated as it gets with photosystems today (Figure 1) [1]. It is composed of three co-axial π-stacks that are grown from an indium tin oxide (ITO) surface. With lower frontier molecular orbital (FMO) levels, the “yellow” stacks can transport photogenerated electrons toward the

• occasional contributions to improve or innovate in the field of organic synthesis. Schematic structure of photosystem 1 on indium tin oxide (ITO, grey) with antiparallel gradients in hole (p, h+) and electron (n, e−) transporting coaxial channels. HOMO (solid) and LUMO levels (dashed) of all components

An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

• Zhiyuan Ma,
• Feng Ni,
• Grace H. C. Woo,
• Sie-Mun Lo,
• Philip M. Roveto,
• Scott E. Schaus and
• John K. Snyder

Beilstein J. Org. Chem. 2012, 8, 829–840, doi:10.3762/bjoc.8.93

• transesterification reaction were screened. Boronic acid [91] and indium(III) iodide [92] yielded no transesterification product with propargyl alcohol, while Ti(OiPr)4 [93] gave only a trace of the desired product, with mostly detosylation resulting. Otera’s catalyst [94] proved to be optimal, giving cycloaddition

Synthesis and characterization of a novel carboxyl group containing (co)polyimide with sulfur in the polymer backbone

• Miroslav Mrsevic,
• David Düsselberg and
• Claudia Staudt

Beilstein J. Org. Chem. 2012, 8, 776–786, doi:10.3762/bjoc.8.88

• groups to attach inorganic, high-refractive-index materials, such as ITO (indium tin oxide) or TiO2, to the polymer backbone to further improve the refractive index of such a (co)polyimide [20][21][22]. In this work, we report on the synthesis and characterization of fluorinated, DABA- and sulfur

Formation of carbohydrate-functionalised polystyrene and glass slides and their analysis by MALDI-TOF MS

• Martin J. Weissenborn,
• Johannes W. Wehner,
• Christopher J. Gray,
• Robert Šardzík,
• Claire E. Eyers,
• Thisbe K. Lindhorst and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2012, 8, 753–762, doi:10.3762/bjoc.8.86

• in the mass-to-charge ratio [14]. Previous attempts to get around this issue have involved coating polymer or glass surfaces with a thin membrane of conductive material, such as gold, carbon or indium-tin oxide [15][16][17], or the addition of electron-accepting additives, such as methyl viologen

Sonogashira–Hagihara reactions of halogenated glycals

• Dennis C. Koester and
• Daniel B. Werz

Beilstein J. Org. Chem. 2012, 8, 675–682, doi:10.3762/bjoc.8.75

• the use of these compounds in the synthesis of aryl-, allyl- and benzyl-C-glycosides [16]. The group of Minehan described another fascinating approach to aryl-C-glycosides in 2003 [17]. They showed that aryl-C-glycosides can be prepared from glycalyl indium(III) compounds (e.g., 4) in a Pd-catalyzed

Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles

• Daniel J. Tate,
• Rémi Anémian,
• Richard J. Bushby,
• Suwat Nanan,
• Stuart L. Warriner and
• and Benjamin J. Whitaker

Beilstein J. Org. Chem. 2012, 8, 120–128, doi:10.3762/bjoc.8.14

• calibrated with indium (mp 156.60, ΔH = 28.53 J·g−1) and a heating/cooling rate of 10 °C·min−1. Time-of-flight photoconductivity studies The cells were assembled in a laminar-flow hood to avoid contamination by dust or grease. Each ITO-coated glass slide was connected to a copper wire by epoxy resin (Aradite

Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

• Anne T. Hylden,
• Eric J. Uzelac,
• Zeljko Ostojic,
• Ting-Ting Wu,
• Keely L. Sacry,
• Krista L. Sacry,
• Lin Xi and
• T. Nicholas Jones

Beilstein J. Org. Chem. 2011, 7, 1323–1326, doi:10.3762/bjoc.7.155

• -alkoxy-2-cyclohexenones proceeds in good yields (58–90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2

• (26%). Titanium(IV) chloride was also screened, however no cyclization was observed. A dramatic increase in yield (71%) was obtained with the aid of indium(III) chloride. Additional metal chloride salts have been screened under our cyclization conditions (Table 1, entries 5–8). Although these salts

• promoted the desired cyclization, they were not found to be as effective as indium(III) chloride. We did not observe formation of the alternative 5-membered cyclic product. This result is consistent with those reported by Smit whose acyclic cases led exclusively to acylation at the unsubstituted end of

Nano copper oxide catalyzed synthesis of symmetrical diaryl sulfides under ligand free conditions

• K. Harsha Vardhan Reddy,
• V. Prakash Reddy,
• A. Ashwan Kumar,
• G. Kranthi and
• Y.V.D. Nageswar

Beilstein J. Org. Chem. 2011, 7, 886–891, doi:10.3762/bjoc.7.101

• [10][11], Alzheimer’s and Parkinson’s diseases [12]. During the last decades, transition and boron group metals, such as palladium [13][14][15][16][17][18], nickel [19][20], copper [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37], iron [38], indium [39][40], lanthanum [41] and

Gold-catalyzed propargylic substitutions: Scope and synthetic developments

• Olivier Debleds,
• Eric Gayon,
• Emmanuel Vrancken and
• Jean-Marc Campagne

Beilstein J. Org. Chem. 2011, 7, 866–877, doi:10.3762/bjoc.7.99

• Friedel–Crafts type reactions with benzylic and propargylic alcohols. Shortly after, Sanz and Zhan discovered, that these reactions could also be carried out under Brønsted acid and FeCl3 catalysis, respectively [26][27][28][29]. Later, the use of copper, indium, bismuth, scandium, ytterbium

Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

• Benito Alcaide and
• Pedro Almendros

Beilstein J. Org. Chem. 2011, 7, 622–630, doi:10.3762/bjoc.7.73

• introduction of the allenyl group at the C4-position of 2-azetidinones with the help of organo–indium reagents. The best results, among the several reaction conditions examined for the incorporation of the allene moiety in the four-membered ring, were obtained when the organo–indium reagent was generated in

• situ from the reaction of 2.0 equivalents of indium with 3.0 equivalents of substituted propargyl bromide in the presence of 3.0 equivalents of KI. The best solvent from those that were screened (DMF, THF, C6H6, and C6H5CH3) was found to be DMF. Because further functionalization of the allene group

Unusual behavior in the reactivity of 5-substituted-1H-tetrazoles in a resistively heated microreactor

• Bernhard Gutmann,
• Toma N. Glasnov,
• Tahseen Razzaq,
• Walter Goessler,
• Dominique M. Roberge and
• C. Oliver Kappe

Beilstein J. Org. Chem. 2011, 7, 503–517, doi:10.3762/bjoc.7.59

• calibration curve established from 1.000 g Pd/L standard (CPI International). Indium was used as the internal standard. The element screening in the digests of the “NMP/AcOH/H2O mixtures” was performed in the semi-quantitative analysis mode using the Merck VI ICPMS standard for calibration. For both