Olefin metathesis in multiblock copolymer synthesis

• Maria L. Gringolts,
• Yulia I. Denisova,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21

• (Scheme 7). In more detail, the synthesis included ROMP of NB octyl ester or NB by means of metal coordination using the obtained telechelic polymers methyl triglycol ester in the presence of the bimetallic ruthenium catalyst followed by the addition of an excess of either a Pd-containing chain terminator

Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles

• James T. Fletcher,
• Matthew D. Hanson,
• Joseph A. Christensen and
• Eric M. Villa

Beilstein J. Org. Chem. 2018, 14, 2098–2105, doi:10.3762/bjoc.14.184

• -temperature conditions, such as commonly used in preparing metal coordination compounds. While the pairing of electron-rich formyltriazoles with electron-poor amines slows the rate of rearrangement, it does not preclude the ability of such analogs to rearrange significantly into scrambled analogs. Among the

Metal-mediated base pairs in parallel-stranded DNA

• Jens Müller

Beilstein J. Org. Chem. 2017, 13, 2671–2681, doi:10.3762/bjoc.13.265

• be seen, base pairs including at least one 2PyrPC moiety display the largest stabilization, which points towards an involvement of the endocyclic pyridyl nitrogen atom in metal coordination particularly for the parallel-stranded duplexes. For the shorter 12-mer duplexes, the stabilizing effect of

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• . Gabapentin was also used by Quaresma et al. [124] in the synthesis by manual grinding of seventeen new metal coordination networks with Y(III), Mn(II) and several lanthanide chlorides (LnCl3), Ln = La3+, Ce3+, Nd3+, and Er3+. Ten out of these compounds were structurally characterized and represent the first

A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation

• Wangkhem P. Singh and
• Rajkumar S. Singh

Beilstein J. Org. Chem. 2017, 13, 138–149, doi:10.3762/bjoc.13.17

• -stacking, donor–acceptor interaction, electrostatic, metal coordination, hydrophobic forces or van der Waals’ interactions [4][5][6]. We know a great deal about the aggregation behaviour of gelator molecules from many studies conducted during the past several years. However, rational design and accurate

• ][21][22]. As mentioned above, developing a new gelator is still largely a trial and error method. The most widely used design strategy involves the inclusion of structural components favouring intermolecular non-covalent interactions (like H-bonding, π-stacking, donor–acceptor interaction, metal

• coordination, ionic, hydrophobic forces, etc.) into the gelator molecular structure and studying their gelation behaviour. H-bonding interaction (present in amide, urea, carbamate linkages, etc) alone or in combination with other interactions is the most extensively used strategy in the design of gelators [23

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

• Lucie Brulíková,
• Aidan Harrison,
• Marvin J. Miller and
• Jan Hlaváč

Beilstein J. Org. Chem. 2016, 12, 1949–1980, doi:10.3762/bjoc.12.184

• –Alder products 91, 93, 95 and 97. Regiocontrol of the reaction between 3-dienyl-2-azetidinones and nitrosobenzene due to change in a single stereocenter. Regiocontrol of the reaction between diene 111 and 2-methyl-6-nitrosopyridine (112) due to metal coordination. Asymmetric hetero-Diels–Alder reactions

From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• entirely different approach to the assembly of container molecules; up until that point strategies such as hydrogen bonding or metal coordination were the focus of attention. Our first investigations with octa-acid looked at assembly around steroids [31]. There was obviously a personal reason for this, but

Creating molecular macrocycles for anion recognition

• Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

• purpose of transition-metal coordination, an area in which I received my Ph.D. training with Keith Gordon. I asked my postdoctoral co-worker at the time, Yongjun Li, to assist with testing the idea. We prepared a series of analogs to the common terpyridine ligand (Figure 4a,b). Once made, they indeed

Versatile deprotonated NHC: C,N-bridged dinuclear iridium and rhodium complexes

• Albert Poater

Beilstein J. Org. Chem. 2016, 12, 117–124, doi:10.3762/bjoc.12.13

• thousands of papers have presented and described the NHC based catalysis, bearing a carbene–metal coordination [7], catalytically few efforts have been dedicated to other types of coordination of the NHC with the metal. Braunstein and collaborators have smartly faced the challenge to mix the reactivity of

Effective immobilisation of a metathesis catalyst bearing an ammonium-tagged NHC ligand on various solid supports

• Krzysztof Skowerski,
• Jacek Białecki,
• Stefan J. Czarnocki,
• Karolina Żukowska and
• Karol Grela

Beilstein J. Org. Chem. 2016, 12, 5–15, doi:10.3762/bjoc.12.2

• of remotely functionalised ligands within the metal coordination sphere. A very efficient covalent immobilisation through anionic ligands was reported by Buchmeiser et al., who synthesised a series of monolith-supported catalysts (such as 1) which gave metathesis products with extremely low residual

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• bonding, metal coordination, CT interaction, π···π stacking, van der Waals interaction, etc.) play an important role in the formation of the three-dimensional (3D) crystal structures [5]. For the construction of nanostructured objects, π···π, S···S, and other weak intermolecular interactions first

Ruthenium indenylidene “1^st generation” olefin metathesis catalysts containing triisopropyl phosphite

• Stefano Guidone,
• Fady Nahra,
• Alexandra M. Z. Slawin and
• Catherine S. J. Cazin

Beilstein J. Org. Chem. 2015, 11, 1520–1527, doi:10.3762/bjoc.11.166

• general, the commonly used Ru(II)-based pre-catalysts have five ligands in the metal coordination sphere and adopt a distorted square pyramidal geometry (Figure 1). The basic components of this structure include two L-type ligands mutually trans (e.g., phosphines and N-heterocyclic carbene) and two

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

• unit to prepare new charge transfer salts where both the dipolar moment and the possibility of metal coordination and other interactions mediated by the cyano group can be further explored to obtain compounds with interesting properties. Experimental Materials and methods Elemental analyses of the

Self-assembly of heteroleptic dinuclear metallosupramolecular kites from multivalent ligands via social self-sorting

• Christian Benkhäuser and
• Arne Lützen

Beilstein J. Org. Chem. 2015, 11, 693–700, doi:10.3762/bjoc.11.79

• concepts [13], (iii) metal coordination specifics as pioneered by J.-M. Lehn with metal centers that prefer five-fold coordination [14], or (iv) charge-separation effects as utilized by P. J. Stang [15]. As part of our ongoing efforts to develop general guidelines for the (diastereo)selective self-assembly

• alkyne 11 in 96% yield [28]. Finally, a two-fold Sonogashira reaction with 1,3-diiodobenzene afforded the desired bis(2,2’-bipyridine) ligand 2 in quantitative yield. Metal coordination After the successful synthesis we prepared a DMSO solution of copper(I) ions, added it to the ligands (rac)-1 and 2

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

Phosphinocyclodextrins as confining units for catalytic metal centres. Applications to carbon–carbon bond forming reactions

• Matthieu Jouffroy,
• Rafael Gramage-Doria,
• David Sémeril,
• Dominique Armspach,
• Dominique Matt,
• Werner Oberhauser and
• Loïc Toupet

Beilstein J. Org. Chem. 2014, 10, 2388–2405, doi:10.3762/bjoc.10.249

• Mizoroki–Heck and asymmetric hydroformylation reactions. The related trans-chelating diphosphine WIDEPHOS (Figure 1) was also tested for comparison purposes in the case of the Mizoroki–Heck coupling studies. Results and Discussion Metal coordination As shown previously, HUGPHOS-1 and HUGPHOS-2 are able to

Towards allosteric receptors – synthesis of β-cyclodextrin-functionalised 2,2’-bipyridines and their metal complexes

• Christopher Kremer,
• Gregor Schnakenburg and
• Arne Lützen

Beilstein J. Org. Chem. 2014, 10, 814–824, doi:10.3762/bjoc.10.77

• was found to proceed smoothly in dry dichloromethane at room temperature to furnish the desired bis(cyclodextrin)-functionalised 2,2’-bipyridines 1, 2, and 3 in very good yields of 92, 93, and 86% yield, respectively (Scheme 5). Metal coordination – effector binding With our three cyclodextrin

Self-assembly of metallosupramolecular rhombi from chiral concave 9,9’-spirobifluorene-derived bis(pyridine) ligands

• Rainer Hovorka,
• Sophie Hytteballe,
• Torsten Piehler,
• Georg Meyer-Eppler,
• Filip Topić,
• Kari Rissanen,
• Marianne Engeser and
• Arne Lützen

Beilstein J. Org. Chem. 2014, 10, 432–441, doi:10.3762/bjoc.10.40

• second bis(pyridine) ligand (S)-6 in a two-fold Suzuki reaction. Metal coordination After the successful synthesis we mixed solutions of ligands 3 and 6 and [(dppp)Pd(OTf)2] or [(dppp)Pt(OTf)2] and characterised the resulting complexes by 1H, 31P, 1H 2D-DOSY NMR, ESI-MS, and single crystal X-ray

Intermediates in monensin biosynthesis: A late step in biosynthesis of the polyether ionophore monensin is crucial for the integrity of cation binding

• Wolfgang Hüttel,
• Jonathan B. Spencer and
• Peter F. Leadlay

Beilstein J. Org. Chem. 2014, 10, 361–368, doi:10.3762/bjoc.10.34

• also engaged in hydrogen bonding to the secondary alcohol borne at C-25, while the other carboxylate atom is engaged in an H-bond to the NH group of the urethane, thus maintaining the stability of the pseudocyclic structure [39]. The very different metal coordination pattern seen in dehydroxymonensin A

Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers

• Samir Kundu,
• Babli Roy and
• Basudeb Basu

Beilstein J. Org. Chem. 2014, 10, 26–33, doi:10.3762/bjoc.10.5

• food-processing industry [4][5][6][7][8]. For example, organosulfur compounds in garlic are often used in food-processing industries as flavouring and preservative agents and are also used as herbal medicine [4]. Dithioethers are commonly employed as ligands in preparing metal-coordination complexes

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

Design and synthesis of quasi-diastereomeric molecules with unchanging central, regenerating axial and switchable helical chirality via cleavage and formation of Ni(II)–O and Ni(II)–N coordination bonds

• Vadim A. Soloshonok,
• José Luis Aceña,
• Hisanori Ueki and
• Jianlin Han

Beilstein J. Org. Chem. 2012, 8, 1920–1928, doi:10.3762/bjoc.8.223

• assumed that the pentadentate ligand 4 upon coordination with d8 metals will give rise to tetra-coordinated square-planar complexes 5 and 6. The presence of coordinated and noncoordinated groups A and E, positioned up or down relative to the metal coordination plane, will create an element of axial

Azobenzene dye-coupled quadruply hydrogen-bonding modules as colorimetric indicators for supramolecular interactions

• Yagang Zhang and
• Steven C. Zimmerman

Beilstein J. Org. Chem. 2012, 8, 486–495, doi:10.3762/bjoc.8.55

• ]. Noncovalent hydrogen bonding, electrostatic interactions, π–π stacking and metal coordination have been used alone and in concert to assemble a broad range of building blocks, from small molecules [4][5][6][7] to polymers [8][9] including dendrimers [10][11]. Among these noncovalent interactions, hydrogen

Self-assembly of Ru₄ and Ru₈ assemblies by coordination using organometallic Ru(II)₂ precursors: Synthesis, characterization and properties

• Sankarasekaran Shanmugaraju,
• Dipak Samanta and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2012, 8, 313–322, doi:10.3762/bjoc.8.34

• energy region compared to those of the starting acceptors (1a, νCO = 1623.7 cm−1; 1b, νCO = 1605.0 cm−1) due to the ligand-to-metal coordination. The appearance of a single peak in the 19F NMR spectrum at −81.03 ppm (2a) or −79.8 ppm (2b) indicated the presence of triflate counter anions in the same

• δ 5.14–5.81 ppm. Notably, the 1H signals of the protons of L exhibited a significant downfield shift compared to the unbound linker due to the loss of electron density upon ligand-to-metal coordination (Figure 1 and Figure S2, Supporting Information File 1). The high solubility of the assemblies in

• common organic solvents and the symmetric nature of 1H NMR spectra primarily ruled out the formation of a polymer with extended coordination. Although the initial characterization of the self-assembled species by NMR spectroscopy intimated the ligand-to-metal coordination, it does not provide any