Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• ]. In the first stage, the two chloro ligands on the four-coordinate square-planar platinum(II) center of cisplatin are displaced by PEG-b-PAA carboxylate groups to produce PEG-b-PAA-cisplatin micelles. Addition of α-CD results in host–guest complexation of the PEG segments of PEG-b-PAA and subsequent

Copper-catalyzed intermolecular oxyamination of olefins using carboxylic acids and O-benzoylhydroxylamines

• Brett N. Hemric and
• Qiu Wang

Beilstein J. Org. Chem. 2016, 12, 22–28, doi:10.3762/bjoc.12.4

• olefins with a tethered amino or oxygen functionality has been achieved for the construction of a variety of 1,2-oxyamino products, using palladium [19][20], platinum [21], gold [22], copper [23][24][25][26], free-radical initiators [27][28][29], hypervalent iodine [30], and electrochemical oxidation [31

Synthesis, structure, and mechanical properties of silica nanocomposite polyrotaxane gels

• Kazuaki Kato,
• Daisuke Matsui,
• Koichi Mayumi and
• Kohzo Ito

Beilstein J. Org. Chem. 2015, 11, 2194–2201, doi:10.3762/bjoc.11.238

• chromatography (SEC) were purchased from Polymer Source, Inc. Solutions of silica nanoparticle with 15 nm of diameter in N,N-dimethylacetamide was kindly supplied by Nissan Chemical Industries, Ltd. 2-Isocyanatoethyl acrylate was purchased from Showa Denko K.K. Xylene solutions of platinum(0)-1,3-divinyl-1,1,3,3

• triethoxysilyl modified polyrotaxane (TES-PR) Two grams of Acryl-PR previously dried under vacuum was dissolved in anhydrous acetone (40 mL). Triethoxysilane (600 μL) and a xylene solution of platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane dibutyltin dilaurate (200 μL) were added followed by refluxing at

The simple production of nonsymmetric quaterpyridines through Kröhnke pyridine synthesis

• Isabelle Sasaki,
• Jean-Claude Daran and
• Gérard Commenges

Beilstein J. Org. Chem. 2015, 11, 1781–1785, doi:10.3762/bjoc.11.193

• pyridine synthesis; Mannich bases; platinum; X-ray diffraction; Findings Polypyridines have been demonstrated to be useful building blocks in metallo-supramolecular chemistry [1][2][3]. In particular, polypyridines joined at the 2,6-position have the ability to accommodate different coordination numbers

• is easily introduced on the 2,2’-bipyridine or 2,2’:6’,2”:6”-terpyridine moieties [31][32]. In fact, the use of a chiral enone (i.e., (−)-myrtenal) led to the chiral 5,6-substituted quaterpyridine 8. The corresponding platinum complex 9 was obtained by a classical synthesis, which entails the

• reaction of the platinum salt in the presence of the ligand in a mixture of acetonitrile and water under reflux for some hours (see Supporting Information File 1). The quaterpyridines and the platinum complex 9 were fully characterized by NMR, EIMS, and elemental analysis. In particular, for 5, 8 and 9

Tetrathiafulvalene-based azine ligands for anion and metal cation coordination

• Awatef Ayadi,
• Aziz El Alamy,
• Olivier Alévêque,
• Magali Allain,
• Nabil Zouari,
• Mohammed Bouachrine and
• Abdelkrim El-Ghayoury

Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149

• were performed in a three-electrode cell equipped with a platinum millielectrode as the working electrode , a platinum wire as a counter electrode and a silver wire Ag/Ag+ used as a reference electrode. The electrolytic media involved a 0.1 mol/L solution of (n-Bu4N)PF6 in dichloromethane/acetonitrile

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• followed by cross metathesis. The molecule shows a hypsochromic shift which indicates rigidity in the molecule compared with the other linear molecules. Enyne metathesis: In 1998, Fürstner and co-workers [147] have employed platinum(II)-catalyzed enyne metathesis as a key step to form cyclophane ring

• bromide gave the enyne product 166 (92%), which on further acylation of terminal alkyne with butanoyl chloride delivered compound 167 (82%). Then, it was subjected to an enyne metathesis with simple platinum salts such as PtCl2 and PtCl4 to give product 168 (79%). A subsequent reduction of the α,β

Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones

• Flavia Pop and
• Narcis Avarvari

Beilstein J. Org. Chem. 2015, 11, 1105–1111, doi:10.3762/bjoc.11.124

• . Electrochemical studies: Cyclic voltammetry measurements were carried out with a Biologic SP-150 potentiostat in a glove box containing dry, oxygen-free (<1 ppm) argon at 293 K, by using a three-electrode cell equipped with a platinum millielectrode of 0.126 cm2 area, an Ag/Ag+ pseudo-reference electrode and a

• platinum-wire counter electrode. The potential values were then re-adjusted with respect to the saturated calomel electrode (SCE). The electrolytic media involved a 0.1 mol/L solution of (n-Bu4N)PF6 in CH2Cl2/acetonitrile 1:1. All experiments were performed at room temperature at 0.1 V/s. Molecular

A hybrid electron donor comprising cyclopentadithiophene and dithiafulvenyl for dye-sensitized solar cells

• Gleb Sorohhov,
• Chenyi Yi,
• Michael Grätzel,
• Silvio Decurtins and
• Shi-Xia Liu

Beilstein J. Org. Chem. 2015, 11, 1052–1059, doi:10.3762/bjoc.11.118

• , multiplet. HRMS data were obtained with electrospray ionization (ESI). Cyclic voltammetry was performed in a three-electrode cell equipped with a platinum-disk working electrode, a glassy carbon counter electrode, and Ag/AgCl was used as the reference electrode. The electrochemical experiments were carried

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

• Yoann Cotelle,
• Marie Hardouin-Lerouge,
• Stéphanie Legoupy,
• Olivier Alévêque,
• Eric Levillain and
• Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

• ]. Electrochemical measurements were carried out using a platinum wire counter electrode and a silver wire as a quasi-reference electrode with a Biologic SP-150 potentiostat driven by the EC-Lab software including ohmic drop compensation. Experiments were recorded in dry HPLC-grade acetonitrile and dichloromethane

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

• Sandrina Oliveira,
• Dulce Belo,
• Isabel C. Santos,
• Sandra Rabaça and
• Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 951–956, doi:10.3762/bjoc.11.106

• as solvents respectively and TMS the internal reference. UV–vis spectra were recorded on an UV-1800 Shimadzu spectrophotometer. Cyclic voltammetry data were obtained using a BAS C3 Cell Stand. The voltammograms were obtained at room temperature with a scan rate of 100 mV/s, platinum wire working and

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

• Huixin Jiang,
• Virginia Mazzanti,
• Christian R. Parker,
• Søren Lindbæk Broman,
• Jens Heide Wallberg,
• Karol Lušpai,
• Adam Brincko,
• Henrik G. Kjaergaard,
• Anders Kadziola,
• Peter Rapta,
• Ole Hammerich and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104

• Supporting Information File 1, Figure S4) using cyclic voltammetry (with a platinum-wire working electrode in the presence of internal ferrocene potential marker). They are very close to 1a and 2a, respectively, as expected. Using 3b as a reference compound, it is seen that all the other compounds are

• acyclic components, 1a and 5 (−1.65 V and −2.35 V vs Fc/Fc+). UV–vis–NIR and EPR spectra of oxidized species The EPR and optical (UV–vis–NIR) properties of the oxidized species were studied by in situ spectroelectrochemistry in CH2Cl2 (Bu4NPF6) at a platinum mesh electrode. Even at low scan rate of 2 mV s

• spectrolectrochemical response found for sample 2b in CH2Cl2 (Bu4NPF6) at a platinum mesh electrode. A new dominating absorption band with maximum at 842 nm having a rich vibronic pattern was observed during the in situ reduction in the region of the first cathodic voltammetric peak (a similar absorption at λmax 845 nm

TTFs nonsymmetrically fused with alkylthiophenic moieties

• Rafaela A. L. Silva,
• Bruno J. C. Vieira,
• Marta M. Andrade,
• Isabel C. Santos,
• Sandra Rabaça,
• Dulce Belo and
• Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 628–637, doi:10.3762/bjoc.11.71

• voltammograms were obtained at room temperature with a scan rate of 100 mV/s, platinum wire working and counter electrodes and a Ag/AgNO3 reference electrode. The measurements were performed on fresh solutions with a concentration of 10−3 M, in CH2Cl2, that contained n-Bu4NPF6 (10−1 M) as the supporting

Electrochemical oxidation of cholesterol

• Jacek W. Morzycki and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2015, 11, 392–402, doi:10.3762/bjoc.11.45

• activated oxygen species that regioselectively oxidized the tertiary C–H bonds. The reactions were carried out under constant current conditions in aqueous acetonitrile with Tl(TFA)3, HMP, LiClO4 and by bubbling with O2 gas with platinum electrodes in an undivided cell. The starting cholesterol was

• -compartment glass cell equipped with platinum mesh electrodes (cathode and anode) was filled with a cholesteryl acetate (1a) solution in acetonitrile containing ammonium tetrafluoroborate as a supporting electrolyte. The constant potential technique mainly afforded 7-hydroxylated products (7a and 8a; 19–38

• galvanostatic conditions at a platinum electrode in DMF containing 6% water with NaBr as a supporting electrolyte. A mixture of products was formed, among them “3,5,6-trihydroxycholesterol” (probably cholesta-3β,5ξ,6ξ-triol), 7-oxocholesterol (9), 5,6-epoxycholesterol (10), and 7-ketocholesterol were identified

IR and electrochemical synthesis and characterization of thin films of PEDOT grown on platinum single crystal electrodes in [EMMIM]Tf₂N ionic liquid

• Andrea P. Sandoval,
• Marco F. Suárez-Herrera and
• Juan M. Feliu

Beilstein J. Org. Chem. 2015, 11, 348–357, doi:10.3762/bjoc.11.40

• , E-03080 Alicante, Spain 10.3762/bjoc.11.40 Abstract Thin films of PEDOT synthesized on platinum single electrodes in contact with the ionic liquid 1-ethyl-2,3-dimethylimidazolium triflimide ([EMMIM]Tf2N) were studied by cyclic voltammetry, chronoamperometry, infrared spectroscopy and atomic force

• electrochemical properties, as the ionic resistance or the electrocatalytic activity, of PEDOT are affected by the surface energy state of the electrode [6]. For example, it was found that the ionic resistance of the PEDOT films electrochemically synthesized on platinum electrodes increases in the order Pt(100

• ) during the first cycles. Figure 1 clearly shows that the electrochemical polymerization of EDOT on platinum electrodes is a surface sensitive reaction. It was found that Pt(111) has the highest electrocatalytic activity for the EDOT oxidation reaction followed by Pt(110) and finally Pt(100). Taking into

Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines

• Carolin Edinger,
• Jörn Kulisch and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2015, 11, 294–301, doi:10.3762/bjoc.11.34

• (6c and 7c, R2 = Ph) require prolonged reaction times and render slightly lower yields. Electrochemical reduction of 8-substituted menthone oximes The electrolyses were carried out in a divided cell using a Nafion® sheet as separator and platinum as anodic material. Since previous studies revealed

Photovoltaic-driven organic electrosynthesis and efforts toward more sustainable oxidation reactions

• Bichlien H. Nguyen,
• Robert J. Perkins,
• Jake A. Smith and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2015, 11, 280–287, doi:10.3762/bjoc.11.32

• MeOH (0.03 M) with lithium perchlorate (0.03 M, 1.0 equiv) in a flame-dried three-necked round-bottomed flask at room temperature under an argon atmosphere. The flask was equipped with a RVC anode and platinum wire cathode using two of the three necks of the flask. The photovoltaic system was inserted

Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

• Taiki Kojima,
• Rika Obata,
• Tsuyoshi Saito,
• Yasuaki Einaga and
• Shigeru Nishiyama

Beilstein J. Org. Chem. 2015, 11, 200–203, doi:10.3762/bjoc.11.21

• –11), and finally the optimized conditions for the synthesis of 2 (85% yield, racemate/meso = 74:26) were acquired in the case of 2.5 F/mol current (Table 1, entry 11). To check for a different behavior of the BDD electrode, several electrode materials, including glassy carbon (GC), platinum (Pt), and

Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes

• Philipp Röse,
• Steffen Emge,
• Jun-ichi Yoshida and
• Gerhard Hilt

Beilstein J. Org. Chem. 2015, 11, 174–183, doi:10.3762/bjoc.11.18

• undivided cell, using platinum foil electrodes (constant current 10 mA). In this investigation only diphenyl diselenide was used as selenium source. These reaction conditions led to the formation of products of type 3 as exclusive diastereomers (Scheme 2). The cyclisation of 2 could lead to a number of

• acetonitrile. Then, the cell was equipped with a platinum plate anode and cathode and electrolysed under a constant current (10 mA, 6.67 mA/cm2) at 20 °C until completion was detected by TLC and GC–MS analysis. Then, 15 mL water were added, the mixture was extracted with diethyl ether (three times 15 mL

3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates

• Aneta M. Tomkiel,
• Adam Biedrzycki,
• Jolanta Płoszyńska,
• Dorota Naróg,
• Andrzej Sobkowiak and
• Jacek W. Morzycki

Beilstein J. Org. Chem. 2015, 11, 162–168, doi:10.3762/bjoc.11.16

• with TBDMSCl in DMF in the presence of imidazole and DMAP. All of these compounds proved to be electrochemically active. Cyclic voltammograms measured in dichloromethane on a platinum electrode indicated that the main oxidation peak for the substances occurred within 1.8–2.0 V (vs Ag/AgNO3 in MeCN

• electrode was a Bioanalytical Systems platinum inlay (1 mm in diameter), the auxiliary electrode was a platinum mesh (contained in a glass tube with a medium porosity glass frit), and the reference electrode was Ag/0.1 M AgNO3 in acetonitrile. The potential of the electrode vs the ferrocene/ferricinium ion

• eliminate chloride ions that are formed by the reduction of dichloromethane. The solutions in both compartments were stirred during electrolysis and, additionally, a continuous flow of argon was applied in the anodic compartment. A platinum mesh was used as a cathode and a platinum plate (2 × 1.5 cm) was

Highly selective electrochemical fluorination of dithioacetal derivatives bearing electron-withdrawing substituents at the position α to the sulfur atom using poly(HF) salts

• Bin Yin,
• Shinsuke Inagi and
• Toshio Fuchigami

Beilstein J. Org. Chem. 2015, 11, 85–91, doi:10.3762/bjoc.11.12

• derivatives (dithioacetals) were prepared, and their oxidation potentials () were measured by cyclic voltammetry in an anhydrous acetonitrile (MeCN) solution containing n-Bu4NBF4 (0.1 M) using a platinum disk working electrode and a saturated calomel electrode (SCE) as the reference electrode. All compounds

• -withdrawing effect of a substituent greatly affects the electron-transfer step from the substrate to the anode. At first, anodic fluorination of ethyl α,α-bis(phenylthio)acetate (1b) [30][31] was carried out at platinum plate electrodes in an undivided cell using various solvents in the presence of Et3N·3HF

The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon–carbon bond formation via electrogenerated N-acyliminium ions

• Alan M. Jones and
• Craig E. Banks

Beilstein J. Org. Chem. 2014, 10, 3056–3072, doi:10.3762/bjoc.10.323

• anode and a platinum wire coil is used as the cathode; the flow cell is placed into a dry ice bath to maintain the −78 °C temperature required. Cation flow systems can be used to prepare individual molecules and combined with the concept of combinatorial chemistry to generate libraries of compounds. A

• is attached either to the carbamate or amide (Figure 5) [69][70][71] (using a platinum anode and tungsten cathode electrochemical set-up) [69] or the use of Cu-PyBox chiral ligand systems [72]. The cation pool method can be adapted to a multicomponent reaction (MCR) when an N-acyliminium ion is

• nazlinine 117 (Scheme 26) using a commercial electrochemical flow cell which allowed the electrolyte loading to be reduced yet still obtained high conversion and product purity [101]. Interestingly, the use of steel or platinum electrode resulted in no conversion to the product and was only possible using a

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• combined with moieties covalently interacting with DNA and RNA. One of the most promising examples reported recently revealed that in a series of mono functional, cationic platinum(II) compounds, phenanthriplatin displayed a greater cytotoxic activity than either cisplatin or oxaliplatin despite a fact

Recent advances in the electrochemical construction of heterocycles

• Robert Francke

Beilstein J. Org. Chem. 2014, 10, 2858–2873, doi:10.3762/bjoc.10.303

• platinum electrodes. Among several electrolyte compositions, NaClO4 in a 7:1 mixture of dioxane/water proved to be the most efficient one. Halogen substituents on the phenol unit are tolerated under the described reaction conditions. In contrast, electron rich substrates (R = OMe) render unsatisfactory

• vs. SCE. Furthermore, the use of PTFE-coated platinum as working electrode proved to be beneficial. Presumably, the reaction sequence proceeds within the hydrophobic electrode coating, where the highly reactive intermediate 53 is protected from side-reactions and the reaction with the hydrophobic

• approach proceeds reagent- and catalyst-free. Both electron-rich and electron-deficient olefins can be efficiently converted. The electrolysis is carried out under potentiostatic conditions in a divided cell at room temperature using a platinum working electrode. A mixture of triethylamine and glacial

Detonation nanodiamonds biofunctionalization and immobilization to titanium alloy surfaces as first steps towards medical application

• Juliana P. L. Gonçalves,
• Afnan Q. Shaikh,
• Manuela Reitzig,
• Daria A. Kovalenko,
• Jan Michael,
• René Beutner,
• Gianaurelio Cuniberti,
• Dieter Scharnweber and
• Jörg Opitz

Beilstein J. Org. Chem. 2014, 10, 2765–2773, doi:10.3762/bjoc.10.293

• of a specially designed conical cell, made from acrylic glass, which mounts a titanium based alloy sample inside. Only 1.8 cm2 circular surface of sample is exposed to the electrolyte solution. A platinum wire is used as a counter electrode. Potential is measured against a saturated Ag/AgCl electrode

• time, samples are rinsed in deionized water. Characterization The FTIR measurements were carried out with ALPHA's Platinum ATR from Bruker. The samples were measured in solid state, without previous preparation. Parameters were: 32 scans, 4 cm−1 resolution; wavelength range 4000–400 cm−1. SEM

• was cut every time to observe the layer structure of the titanium alloy. Sample preparation includes carbon coating followed by platinum deposition for sample protection. Proposed functional groups on purified DND surface. ATR-FTIR spectra of species 3 and 6 from Scheme 1 in comparison to O

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

• on a CH Instruments 660A electrochemical workstation with iR compensation using anhydrous dichloromethane as a solvent. The electrodes were glassy carbon, platinum wire, and silver wire as the working, counter, and reference electrodes, respectively. All solutions were degassed (Ar) and contained