Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• catalyst productivity and selectivity [105][106]. Particularly, monoliths featuring a 3D isotropic, hierarchically porous network of narrowly size distributed, interconnected macropores (1–30 μm) and mesopores within the struts (6–50 nm) have shown a unique hydrodynamic behavior in the liquid phase [107

Inclusion complexes of β-cyclodextrin with tricyclic drugs: an X-ray diffraction, NMR and molecular dynamics study

• Franca Castiglione,
• Fabio Ganazzoli,
• Luciana Malpezzi,
• Andrea Mele,
• Walter Panzeri and
• Giuseppina Raffaini

Beilstein J. Org. Chem. 2017, 13, 714–719, doi:10.3762/bjoc.13.70

• antiparallel columns along the crystallographic b axis. Within each column, the molecules are linked by hydrogen bonding involving both the macrocycles and the guest molecules, while interactions between macrocycles link adjacent columns. A large network of H-bonds involving the water molecules contribute to

How and why kinetics, thermodynamics, and chemistry induce the logic of biological evolution

• Addy Pross and
• Robert Pascal

Beilstein J. Org. Chem. 2017, 13, 665–674, doi:10.3762/bjoc.13.66

• relative free energies of reactant (R) and products (P1 and P2). Under kinetic control, P2 would be favoured over P1. Evolution of an autocatalytic network involving a parasite. R: resource; A: autocatalyst; B: predator autocatalyst. Numerical simulation of the system of Figure 3 (k0 = 0.01 M min−1, k1

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• synthesis of the [14C]indene 176, which was next applied for the examination of the indene bioconversion network expressed in Rhodococcus sp. KY1 [79]. The [14C]1-indanone 175 was obtained in the one-pot synthesis involving the Friedel–Crafts acylation of [14C]benzene 173 with chloropropionic acid chloride

Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties

• Maximilian Maier,
• Magnus S. Schmidt,
• Markus Ringwald and
• Christoph P. Fik

Beilstein J. Org. Chem. 2017, 13, 372–383, doi:10.3762/bjoc.13.40

• elucidated the underlying polymerization mechanism. Mechanical testing of the obtained polymers exhibited gradual differences in network densities, depending on the intramolecular arrangement and number of functional groups. Overall, a general building principle for highly reactive, liquid diacrylamides via

• initiate the lactam formation with the internal butene group, whereas there is only one favorable orientation for the external allyl group. Polymer network properties To assess the influence of functionalities on the network densities of the obtained polymers, mechanical data of rod-like samples according

• thus highest apparent network density. This means that ring formation, which in principle should reduce the amount of covalent network points in the cured material, is superimposed by effects of conversion, entanglement and rigidity of the formed polymer. The decreasing trend of flexural modulus from 1

Efficient access to β-vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones

• Vinicius R. Campos,
• Ana T. P. C. Gomes,
• Anna C. Cunha,
• Maria da Graça P. M. S. Neves,
• Vitor F. Ferreira and
• José A. S. Cavaleiro

Beilstein J. Org. Chem. 2017, 13, 195–202, doi:10.3762/bjoc.13.22

• . Acknowledgments We would like to thank the University of Aveiro, the “Fundação para a Ciência e a Tecnologia” (FCT), the European Union, QREN, FEDER and COMPETE for funding the QOPNA research unit (project PEst-C/QUI/UI0062/2013) and the Portuguese National NMR Network (RNRMN). A. T. P. C. Gomes also thanks FCT

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

• Monica Ferro,
• Franca Castiglione,
• Nadia Pastori,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2017, 13, 182–194, doi:10.3762/bjoc.13.21

• interest as drug carriers, since these materials are able to accommodate small drug molecules within their porous network made of CD lipophilic cavities and more hydrophilic polymer channels originated during the cross-linking process with suitable cross-linking agents (CL). The polymer is obtained by

• the polymer network in the solid state. The methodological approach here presented relies upon two different solid state NMR methodologies and it is finally supported by powder X-ray diffraction (PXRD) data. In particular, here we present the use of variable contact time (VCT) cross-polarization 13C

• isolated S spins and an extended network of coupled I spins. The heat capacity of the rare S spins is much lower than that of I spins. According to this model, the spins I are characterized by a rapid spin diffusion so that they behave as a single spin system at a uniform spin temperature. After the

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• structure of dodecaacid C2 (Cn stands for Th symmetrical hexakisadducts C60{C[COO(CH2)n−1COOH]2}6, see Figure 1) revealing a complex hydrogen-bonding network in the crystalline state [57]. Based on this initial finding, we also utilized C2 and elongated derivative C3 as organic connectivity centers in metal

• crystallization of C3 and also synthesized the next homologue C4 starting from malonate 1 [59] according to a standard two-step protocol via a sixfold Bingel reaction followed by acidic deprotection (Scheme 1). As we observed the insertion of MeOH molecules into the hydrogen-bonding network of HFF-1 [57], we also

• top view indicating enlarged intralayer spacing for elongated derivatives (bottom); images are created with PyMOL [58]. Hydrogen bonding network for HFF-3 (left, hydrogen bonds yellow) and porous channels along the c axis filled with unbound Et2O molecules (right, Et2O orange, inner pore surface

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• , the knowledge of the binding constants (Kass) is crucial because these values provide an index of host–guest binding forces. CDs can also form exclusion complexes where the CDs are bound to the guest through a H-bond network. For instance, the complexation of [PMo12O40] anion by β- and γ-CD results in

Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents

• Davide Brenna,
• Elisabetta Massolo,
• Alessandra Puglisi,
• Sergio Rossi,
• Giuseppe Celentano,
• Maurizio Benaglia and
• Vito Capriati

Beilstein J. Org. Chem. 2016, 12, 2620–2626, doi:10.3762/bjoc.12.258

• possible interaction between the aldol product and the DES network (Figure 1). Due to its favourable physical and mechanical properties, DES A was selected for the initial screening of the different experimental conditions in continuo. The first experimental set-up that was studied (Figure 1, I) was built

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• (=O) of uracil and the hydrogen bonds network of the side-chains of Gln166, Arg223 and Arg168 are responsible for the strict specificity to uracil and to a lesser extent to thymine [5][6] recognizing the 2C(=O)-3N(H)-4C(=O) fragment as distinct from the 2C(=O)-3N=4C(NH2) part of cytosine. Notably, the

Synthesis of three-dimensional porous hyper-crosslinked polymers via thiol–yne reaction

• Mathias Lang,
• Alexandra Schade and
• Stefan Bräse

Beilstein J. Org. Chem. 2016, 12, 2570–2576, doi:10.3762/bjoc.12.252

• metal-free reaction conditions, high yields and easy purification. Results and Discussion The first network shown here was synthesized by crosslinking the two tetrahedral tetraphenylmethane core structures 1 and 2 via the radical-mediated thiol–yne reaction using AIBN as initiator. The second network

Experimental and theoretical investigations into the stability of cyclic aminals

• Edgar Sawatzky,
• Antonios Drakopoulos,
• Martin Rölz,
• Christoph Sotriffer,
• Bernd Engels and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221

• computational investigations. Acknowledgements M. Decker gratefully acknowledges the German Science Foundation (Deutsche Forschungsgemeinschaft) for financial support (DFG DE1546/6-1 and DE1546/6-3) and the Elite Network of Bavaria for awarding a Ph.D. position to A. Drakopoulos within the International

Robust C–C bonded porous networks with chemically designed functionalities for improved CO₂ capture from flue gas

• Damien Thirion,
• Joo S. Lee,
• Ercan Özdemir and
• Cafer T. Yavuz

Beilstein J. Org. Chem. 2016, 12, 2274–2279, doi:10.3762/bjoc.12.220

• COP-156-amine showed fast and increased CO2 uptake under simulated moist flue gas conditions compared to the starting network and usual industrial CO2 solvents, reaching up to 7.8 wt % uptake at 40 °C. Keywords: C–C bond; CO2 capture; microporous materials; porous polymers; postmodification

• ; Findings Porous polymers are network polymers that are made from multivalent monomers and form permanent pores through the net formation [1]. They differ slightly from cross-linked polymers with more certainty in the location of branching and the type and quantity of functionalities. Also, the rigidity of

• , cyanovinylene bridged porous networks are not studied extensively and our previously reported COP-100 structure [18] suffered from low porosity. In order to obtain a cyanovinylene-bridged porous network with tangible surface area, different core and linker combinations were tested leading to the synthesis of

Hydroxy-functionalized hyper-cross-linked ultra-microporous organic polymers for selective CO₂ capture at room temperature

• Partha Samanta,
• Priyanshu Chandra and
• Sujit K. Ghosh

Beilstein J. Org. Chem. 2016, 12, 1981–1986, doi:10.3762/bjoc.12.185

• HCP-94 was 342 mL/g (Figure 2b). Both low temperature N2 adsorption isotherms were of type-I category and a hysteresis was observed in desorption profiles. The hysteresis in the desorption curves can be explained in terms of a network swelling in the presence of condensed nitrogen [34]. The Howarth

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• polymer, without an activation step, removed 20% of the total metal load in spiked solutions (SS) containing five metals at 10 mg·L−1 each. This could be attributed to surface adsorption and diffusion into the polymer network. However, it was observed that an activation step in an aqueous solution of

• -linking agent BTCA was used, this compound presents four carboxylic functions and a previous study [18] showed that only two of its carboxylic groups reacted with the CD units to form the polymer network, the two remaining ones being available to react with cations through chemisorption (electrostatic

• precipitation and/or physical phenomena (surface adsorption, diffusion into the network and/or hydrogen bonding). This study demonstrated the efficiency of activated polyBTCA-CD to treat the inorganic load, but also to treat the organic pollutants. It can be noted that the analysis of 26 substances present in

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• quite surprised to find that we generated regular spherical and network structures (Figure 3) [24]. This "bricks and mortar" assembly process provides a modular system where structure and stoichiometry of the components drives structure formation. These assemblies set us on a path of generating

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• Scientific Research (Nos. 16K21218 (H.K.) and 15H01049 (T.Y.)) from JSPS, the Cooperative Research Program of “Network Joint Research Center for Materials and Devices”, the Yoshida Education and Foundation (H.K.), the Yashima Environment Technology Foundation (T.Y.), and the KDDI Foundation Research Grant

Discovery of an inhibitor of the production of the Pseudomonas aeruginosa virulence factor pyocyanin in wild-type cells

• Bernardas Morkunas,
• Balint Gal,
• Warren R. J. D. Galloway,
• James T. Hodgkinson,
• Brett M. Ibbeson,
• Yaw Sing Tan,
• Martin Welch and
• David R. Spring

Beilstein J. Org. Chem. 2016, 12, 1428–1433, doi:10.3762/bjoc.12.137

• network with the Las system at the top of the network. The regulator of the pyocyanin biosynthesis genes is RhlR and transcription of the rhlR gene is itself regulated by LasR. Hence, it has been hypothesised that LasR inhibition should result in the attenuation of pyocyanin production [8][9][20]. This

• studies have demonstrated that the straight forward hierarchical QS network (with the las system at the forefront followed by the lower ranked rhl and pqs signalling system) is more elaborate and complex than this hierarchical structure [8][9][30]. Taking these studies into account it is possible that

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

• Daniela Obels,
• Melanie Lievenbrück and
• Helmut Ritter

Beilstein J. Org. Chem. 2016, 12, 1395–1400, doi:10.3762/bjoc.12.133

• water swellable network 3a and 3b. Photographs of water-swollen polymer disks consisting of 1 mol % (3a) and 2.5 mol % (3b) of 2a as cross linker. UV–vis spectra of oligomers 5 (c = 0.16 g/mL, red), 6 (c = 0.63 g/mL, blue) and DFA (c = 0.016 g/mL, grey). Alkylation of N-VP with 1,8-dibromooctane

Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA

• Svetlana V. Vasilyeva,
• Vyacheslav V. Filichev and
• Alexandre S. Boutorine

Beilstein J. Org. Chem. 2016, 12, 1348–1360, doi:10.3762/bjoc.12.128

• and the New Zealand Ministry of Research, Science and Technology for their support with the Dumont d’Urville network grant (EGIDE No 18961YF). We thank Prof. Tom Brown for a gift of THPTA, Dr. Marie-Paule Teulade-Fichou for coumarine M14, Drs. Alain Blond, Arul Marie and Mr. Lionel Dubost for NMR and

Antibiotics from predatory bacteria

• Juliane Korp,
• María S. Vela Gurovic and
• Markus Nett

Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58

• , requires a tight regulatory network in predatory myxobacteria [80]. This is also reflected in the genome of M. xanthus DK1622, which features an unusual high duplication frequency of genes encoding regulatory proteins like serine-threonine kinases and enhancer binding proteins (EBPs) [43]. EBPs are

• myxobacterium. The findings of this study attested a complex regulatory network to M. xanthus DK1622, in which development, predation, and motility are clearly connected to secondary metabolism [84]. Lastly, it should be mentioned that genomic data might also provide the explanation for the predatory behavior

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• Initial Training Network, Project No 608407 (CyclonHit) and OTKA PD 109373 are greatly acknowledged.

Effective in silico prediction of new oxazolidinone antibiotics: force field simulations of the antibiotic–ribosome complex supervised by experiment and electronic structure methods

• Jörg Grunenberg and
• Giuseppe Licari

Beilstein J. Org. Chem. 2016, 12, 415–428, doi:10.3762/bjoc.12.45

• explicitly if they were part of the hydrogen bond network. This working shell was the starting point for the construction of all complexes models used during our MC scans. It includes linezolid, the CCA-N-Phe unit, nucleotides belonging to the r-RNA backbone, a few amino acids, water molecules and cations

Self and directed assembly: people and molecules

• Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

• [80] and the CASE Network was established [81][82][83]. “A scientist has to work very hard to get to the point where he can be lucky.” – Robert B. Woodward (1917–1979) The 7th Catalysis and Sensing for our Environment Symposium was held in Dublin on 9–10 July 2015 and jointly hosted in Ireland by

• Network [85]. Thanks to the CASE Network enduring collaborations have been established in China with outstanding academics including Yun-Bao Jiang [86][87][88][89][90][91][92][93], Xuhong Qian [94][95][96], Yitao Long [97][98][99][100][101][102][103][104][105][106], Weiping Deng [107] ,Weihong Zhu [108

• . I would particularly like to thank The Catalysis and Sensing for our Environment (CASE) network [83] for providing excellent networking opportunities, since many of the results contained in this personal perspective are a direct result of the network.