Automated synthesis of sialylated oligosaccharides

• Davide Esposito,
• Mattan Hurevich,
• Bastien Castagner,
• Cheng-Chung Wang and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 1601–1609, doi:10.3762/bjoc.8.183

• : Experimental procedure and characterization data for new compounds. Supporting Information File 410: 1H and 13C NMR spectra for new compounds. Acknowledgments We acknowledge the Max-Planck Society and the Swiss National Science Foundation (200020-117889) for generous financial support. We thank the National

Asymmetric one-pot sequential Friedel–Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme

• Kengo Akagawa,
• Ryota Umezawa and
• Kazuaki Kudo

Beilstein J. Org. Chem. 2012, 8, 1333–1337, doi:10.3762/bjoc.8.152

• -pot sequential Friedel–Crafts-type alkylation/α-oxyamination. Examples of the one-pot synthesis of oxygenated heteroaromatic compounds. Supporting Information Supporting Information File 340: Typical experimental procedure, spectroscopic data for products, determination of stereochemistry, 1H and 13C

Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10

• Teresa Weise,
• Marco Kai,
• Anja Gummesson,
• Armin Troeger,
• Stephan von Reuß,
• Silvia Piepenborn,
• Francine Kosterka,
• Martin Sklorz,
• Ralf Zimmermann,
• Wittko Francke and
• Birgit Piechulla

Beilstein J. Org. Chem. 2012, 8, 579–596, doi:10.3762/bjoc.8.65

• and solid media, the different trapping material (Super-Q versus polydimethylsiloxane) and the experimental procedure (30 hour trapping versus 2 hour trapping) most likely account for those differences. As discussed above, the suitability of PTR–MS for compound identification is limited. Therefore

Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of “super-trifluoromethyl” arene chemistry and its industry

• Teruo Umemoto,
• Lloyd M. Garrick and
• Norimichi Saito

Beilstein J. Org. Chem. 2012, 8, 461–471, doi:10.3762/bjoc.8.53

• “ZnFCl” species. Finally the byproduct was restricted to less than 1% with ZnF2/ZnCl2/AlCl3 (molar ratio 100:10:5). The detailed experimental procedure is described in Supporting Information File 1. The reaction of PhSF4Cl (2a) with ZnF2 in Table 4 was conducted under nonflowing N2 gas (under the

Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium

• Michael Dobmeier,
• Josef M. Herrmann,
• Dieter Lenoir and
• Burkhard König

Beilstein J. Org. Chem. 2012, 8, 330–336, doi:10.3762/bjoc.8.36

• . Experimental Representative experimental procedure: The alcohol (1 mmol, 1 equiv) is dissolved in 4 mL of toluene. Red phosphorus (0.4 mmol), followed by concentrated hydriodic acid (57% w/w; 3.0 mmol, 3 equiv) is added and the reaction mixture is heated to 80 °C for the stated time, allowed to cool to rt and

Dioxane dibromide mediated bromination of substituted coumarins under solvent-free conditions

• Subrata Kumar Chaudhuri,
• Sanchita Roy and
• Sanjay Bhar

Beilstein J. Org. Chem. 2012, 8, 323–329, doi:10.3762/bjoc.8.35

• electron-withdrawing group. Efficacy of the solvent-free bromination protocol with DD. Solvent-free reactions of substituted coumarins with dioxane dibromide. Supporting Information Supporting Information File 58: General experimental procedure for the preparation of DD and solvent-free bromination of

• (stable for at least three to four months in a refrigerator); (b) a stoichiometric amount of reagent can be used by direct weighing, avoiding excess; (c) no evolution of hazardous bromine vapor during the reaction; (d) the total elimination of the use of toxic organic solvents; (e) a simple experimental

• procedure; (g) an easy work-up; (h) excellent selectivity in case of activated coumarins and (i) good control over the outcome of the reaction by varying the amount of reagent. The aforesaid protocol thus provides an improved procedure for the synthesis of useful bromocoumarins having important

Biocatalytic hydroxylation of n-butane with in situ cofactor regeneration at low temperature and under normal pressure

• Svenja Staudt,
• Christina A. Müller,
• Jan Marienhagen,
• Christian Böing,
• Stefan Buchholz,
• Ulrich Schwaneberg and
• Harald Gröger

Beilstein J. Org. Chem. 2012, 8, 186–191, doi:10.3762/bjoc.8.20

• -called “liquid gas” n-butane (boiling point: −0.5 °C), at a low starting temperature, which was chosen in the range of −5 to 8 °C. For the biotransformation of this liquid gas the following experimental procedure was carried out: First, all components required for the reaction (in a particular solvent

On the mechanism of action of gated molecular baskets: The synchronicity of the revolving motion of gates and in/out trafficking of guests

• Keith Hermann,
• Stephen Rieth,
• Hashem A. Taha,
• Bao-Yu Wang,
• Christopher M. Hadad and
• Jovica D. Badjić

Beilstein J. Org. Chem. 2012, 8, 90–99, doi:10.3762/bjoc.8.9

• understanding of the effective conversion of energy at the molecular level and the preparation of molecular machines [36][37]. Experimental Procedure for 2-D EXSY experiments [25]: A solution of basket 1 and guest 2 in CD2Cl2 (J. Young NMR tube) was cooled to 250.0 ± 0.1 K inside the NMR probe and allowed to

A general and facile one-pot process of isothiocyanates from amines under aqueous conditions

• Nan Sun,
• Bin Li,
• Jianping Shao,
• Weimin Mo,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2012, 8, 61–70, doi:10.3762/bjoc.8.6

• . The following operation was the same as the experimental procedure described above. 4-Fluorophenyl isothiocyanate (CAS No: 1544-68-9, Table 4, entry 1): Yield: 94%; colorless oil; IR (neat): 2079 cm−1; 1H NMR (CDCl3) δ 7.04–7.08 (m, 2H), 7.21–7.24 (m, 2H); GC–EIMS m/z: 153 [M+, 100%]. 4-Chlorophenyl

PEG-embedded KBr₃: A recyclable catalyst for multicomponent coupling reaction for the efficient synthesis of functionalized piperidines

• Sanny Verma,
• Suman L. Jain and
• Bir Sain

Beilstein J. Org. Chem. 2011, 7, 1334–1341, doi:10.3762/bjoc.7.157

• bromine could be detected in the reaction mixture as analyzed by UV−vis spectroscopy; this established the in situ generation of bromine from the reagent during the reaction. Typical experimental procedure Into a stirred mixture of aniline (0.2 g, 2.15 mmol), benzaldehyde (0.2 g, 1.89 mmol), ethyl

Lithium phosphonate umpolung catalysts: Do fluoro substituents increase the catalytic activity?

• Anca Gliga,
• Bernd Goldfuss and
• Jörg M. Neudörfl

Beilstein J. Org. Chem. 2011, 7, 1189–1197, doi:10.3762/bjoc.7.138

• , crystallographic data for compounds 6, 7, 15, computational details for compounds 6, 7 and general procedure for phosphonates as precatalysts in cross benzoin coupling. Supporting Information File 216: Experimental procedure and characterization data. Acknowledgements We are grateful to the Fonds der Chemischen

Reductive amination with zinc powder in aqueous media

• Giovanni B. Giovenzana,
• Daniela Imperio,
• Andrea Penoni and
• Giovanni Palmisano

Beilstein J. Org. Chem. 2011, 7, 1095–1099, doi:10.3762/bjoc.7.125

• the many variables involved in the reaction conditions will allow us to extend this protocol to a wider selection of substrates. Experimental Typical experimental procedure In a round-bottomed flask the aldehyde (5 mmol) and the amine (5 mmol) were suspended in 25 mL of an aq. solution of potassium

Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions

• Deyun Qian and
• Junliang Zhang

Beilstein J. Org. Chem. 2011, 7, 808–812, doi:10.3762/bjoc.7.92

• )-catalyzed Sonogashira couplinga. Supporting Information Supporting information features experimental procedure and spectroscopic data. Supporting Information File 112: Experimental details and spectra of new compounds. Acknowledgements We are grateful to National Natural Science Foundation of China

CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands

• Shuxu Gao,
• Yu Liu and
• Shengming Ma

Beilstein J. Org. Chem. 2011, 7, 396–403, doi:10.3762/bjoc.7.51

• of SnCl2 and NaI in DMF [39][40]; allenols 1f [41], 1g [42], 1h [43], and 1j [44] were prepared as reported. These starting allenols were purified by flash chromatography before use. General experimental procedure for the aerobic oxidation of allenic alcohols 2-Hexyl-1-phenylbuta-2,3-dien-1-one (2a

• MHz, CDCl3) δ 217.1, 194.9, 138.3, 131.9, 129.0, 127.8, 106.7, 79.3, 29.9, 21.1, 13.7 ppm; MS (m/z) 186 (M+, 6.46), 105 (100); IR (neat) 2961, 2932, 2872, 1933, 1651, 1598, 1578, 1447, 1315, 1271 cm−1; HRMS-EI (m/z) calcd for C13H14O+ [M+]: 186.1045; found: 186.1045. General experimental procedure for

Surfactant catalyzed convenient and greener synthesis of tetrahydrobenzo[a]xanthene-11-ones at ambient temperature

• Pravin V. Shinde,
• Amol H. Kategaonkar,
• Bapurao B. Shingate and
• Murlidhar S. Shingare

Beilstein J. Org. Chem. 2011, 7, 53–58, doi:10.3762/bjoc.7.9

• mixture was diluted with distilled water, and then subjected to light microscopy measurement using an ordinary light microscope under 400× magnification. Typical experimental procedure: To a mixture of β-naphthol 1 (0.144 g, 1 mmol), 4-chlorobenzaldehyde 2b (0.140. g, 1 mmol) and dimedone 3 (0.140 g, 1

Identification and synthesis of impurities formed during sertindole preparation

• I. V. Sunil Kumar,
• G. S. R. Anjaneyulu and
• V. Hima Bindu

Beilstein J. Org. Chem. 2011, 7, 29–33, doi:10.3762/bjoc.7.5

• ) 16, Et3N, NaI, CH3CN, reflux; (b) column chromatography (19.1%). Reagents, conditions (and yield): i) (a) mCPBA, MeOH, 40–45 °C; (b) column chromatography (52.2%). Supporting Information Experimental procedure (Supporting Information File 1); HPLC chromatograms, 1H and 13C NMR spectra of compounds 2

Formation of epoxide-amine oligo-adducts as OH-functionalized initiators for the ring-opening polymerization of ε-caprolactone

• Julia Theis and
• Helmut Ritter

Beilstein J. Org. Chem. 2010, 6, 938–944, doi:10.3762/bjoc.6.105

• ][5][6][7][8][9][10]. Some previous works discussed the effective experimental procedure of metal-catalyzed reactions inside a MW oven [11][12]. Among the several types of these catalytic reactions, hydrogenation is probably one of the most useful in synthetic chemistry. Since many laboratory MW

Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride

• Subrata Kumar Chaudhuri,
• Manabendra Saha,
• Amit Saha and
• Sanjay Bhar

Beilstein J. Org. Chem. 2010, 6, 748–755, doi:10.3762/bjoc.6.94

• -unsaturated) with NaBH4 in MeOH at room temperature (30 °C). Reactionsa of 1a and 1b with NaBH4 in anhydrous ether in the presence of protic polar co-solvents. Comparative studya on reduction of various oxo-groups. Supporting Information General experimental procedure for the NaBH4 reduction and the spectral

A novel and efficient method to prepare 2-aryltetrahydrofuran-2-ylphosphonic acids

• Vsevolod V. Komissarov,
• Anatoly M. Kritzyn and
• Jouko J. Vepsäläinen

Beilstein J. Org. Chem. 2010, 6, No. 63, doi:10.3762/bjoc.6.63

• relatively exotic motif – via a one-pot experimental procedure from 4-chloro-1-aryl-1-butanones. The cyclic structure of the synthesized compounds was reliably established by means of various NMR experiments. A mechanism for the cyclization is proposed and it is suggested, that the crucial feature of the

Solvent-free and time-efficient Suzuki–Miyaura reaction in a ball mill: the solid reagent system KF–Al₂O₃ under inspection

• Franziska Bernhardt,
• Ronald Trotzki,
• Tony Szuppa,
• Achim Stolle and
• Bernd Ondruschka

Beilstein J. Org. Chem. 2010, 6, No. 7, doi:10.3762/bjoc.6.7

• SRS5a (32 wt % or 40 wt % KF, respectively) was dissolved in deionized water (50 ml) and was stirred for at least 1.5 h. The solvent was removed by evaporation in vacuum (40 mbar, 60 °C) and stored in a desiccator over potassium hydroxide. Typical experimental procedure: SRS (5 g), aryl bromides (2a–e

Chemoselective reduction of aldehydes by ruthenium trichloride and resin- bound formates

• Basudeb Basu,
• Bablee Mandal,
• Sajal Das,
• Pralay Das and
• Ashis K. Nanda

Beilstein J. Org. Chem. 2008, 4, No. 53, doi:10.3762/bjoc.4.53

• for alcohols (Table 2, entries 3, 5, 6, 8–14, 16, 17) and HRMS data for alcohols (Table 2, entries 3, 12, 13, 14). Supporting Information File 109: General experimental procedure Supporting Information File 110: Spectral data of some selected alcohols Acknowledgements We are grateful to the

Synthesis of methylenebisamides using CC- or DCMT- activated DMSO

• Qiang Wang,
• Lili Sun,
• Yu Jiang and
• Chunbao Li

Beilstein J. Org. Chem. 2008, 4, No. 51, doi:10.3762/bjoc.4.51

• , and the analytical results were within ±0.4% of the theoretical values. Typical experimental procedure N,N′-Methylenedibenzamide (Table 2, entry 1) A mixture of amide (121.4 mg, 1.0 mmol, 1 equiv), CC (222 mg, 1.2 mmol, 1.2 equiv) and dry DMSO (0.5 mL, 7.0 mmol, 7.0 equiv) in dry toluene (8.0 mL) was

Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me₃SiCF₂SO₂Ph and PhSO₂CF₂H reagents catalyzed by chiral quaternary ammonium salts

• Chuanfa Ni,
• Fang Wang and
• Jinbo Hu

Beilstein J. Org. Chem. 2008, 4, No. 21, doi:10.3762/bjoc.4.21

• enantioselective difluoromethylation of aromatic aldehydes with Me3SiCF2SO2Ph and PhSO2CF2H. The enantioselectivity is substrate-dependent and for 2-chlorinated benzaldehydes, an ee up to 64% was obtained. The easy preparation of the chiral cinchonium salts and the convenient experimental procedure make the

Large- scale ruthenium- and enzyme- catalyzed dynamic kinetic resolution of (rac)-1-phenylethanol

• Krisztián Bogár,
• Belén Martín-Matute and
• Jan-E. Bäckvall

Beilstein J. Org. Chem. 2007, 3, No. 50, doi:10.1186/1860-5397-3-50

• Information Supporting Information File 66: Large-scale ruthenium- and enzyme-catalyzed dynamic kinetic resolution of (rac)-1-phenylethanol: Supporting Information. Experimental procedure of DKR of 2 on 1 mol scale and GLC chromatogram of this experiment. Acknowledgements Financial support from the Swedish

Part 1. Reduction of S-alkyl- thionocarbonates and related compounds in the presence of trialkylboranes/air

• Jean Boivin and
• Van Tai Nguyen

Beilstein J. Org. Chem. 2007, 3, No. 45, doi:10.1186/1860-5397-3-45

• by subsequent modifications of the experimental procedure. We therefore returned our attention to the reduction of S-alkylxanthates that sometimes led to poor or irreproducible results when Method A was employed. In particular, some dimerisation of the radical generated from the xanthate was