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

• cations, and have impacted fields that include bioimaging [26][27] and chemosensing [28][29]. Surprisingly, the reported examples partnering 1,2,3-triazole and imine N-donor groups are limited [30][31][32], despite the ubiquity of such Schiff base subunits in coordination chemistry. 4-Iminotriazole

• than originally reported are lacking. With an emerging interest in the 4-imino-1,2,3-triazole motif as coordination chemistry synthon, motivation for revisiting the ring degenerate rearrangements first described by L’abbe is twofold. A better understanding of parameters suppressing this rearrangement

Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

• Rakesh Puttreddy,
• Ngong Kodiah Beyeh,
• S. Maryamdokht Taimoory,
• Daniel Meister,
• John F. Trant and
• Kari Rissanen

Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

• ], coordination chemistry [12][13], biological systems [14] and especially for host–guest (H–G) chemistry [15]. Resorcinarenes can be modified at either the upper rim 2-position, lower rim, or both, to deliver supramolecular structures with the required structure for a given function [16][17][18]. We have shown

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

• Cristina Cebrián and
• Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

• higher geometrical rigidity, which is expected to further decrease molecular distortions. The overall stability of the resulting compound is increased, thus helping to greatly suppress nonradiative deactivation pathways. Although 2,2’:6’,2”-terpyridines showed widespread use in coordination chemistry [42

Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles

• Angélica de Fátima S. Barreto,
• Veronica Alves dos Santos and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2017, 13, 2596–2602, doi:10.3762/bjoc.13.256

• ); Ugi-azide reaction; Introduction Tetrazoles are extensively studied, useful non-natural heterocyclic skeletons with the highest nitrogen content among the stable heterocycles [1][2]. The tetrazole-ring system has a variety of applications in organic chemistry, coordination chemistry, and agriculture

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

• further biomedical/pharmaceutical applications [71], such as cancer therapy [81][82][83]. MOFs combine coordination and supramolecular chemistry. Coordination chemistry is present in the coordination of organic molecules (linkers) to metal ions or clusters (coordination centers), while supramolecular

• and this is certainly an expanding area in the field of organic coordination chemistry. a) Detailed supramolecular packing of a gabapentin–Er network; b) view along the b-axis of the supramolecular packing of a gabapentin–Ce network; c) view of a GBP–Y network showing an infinite 1D chain; d

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• this property was used to increase the water solubility of organic compounds [13][14], polymers [15][16] or ligands for coordination chemistry [17]. It must be noted that for similar compounds, that only differ by the replacement of a carboxylic acid group with a phosphonic acid moiety, the log POW

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• synthesis as well as in inorganic coordination chemistry [172]. However, the mechanochemical organometallic synthesis is still in its infancy due to certain difficulties under solvent-free synthesis. Recently the solid state syntheses of organometallic compounds have become popular. In their pioneering work

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

• Grzegorz Mlostoń,
• Paulina Pipiak,
• Róża Hamera-Fałdyga and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 1900–1906, doi:10.3762/bjoc.13.185

• useful olefination reactions and is another proof for the utility of aryl and hetaryl thioketones in organic synthesis [18]. Another important feature of the presented system with a potential, practical application to materials and coordination chemistry is the release of strictly controlled amounts of

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• gives access to diverse chemical structures which could be considered for further studies, e.g., the biological activity of the triazole-based compounds and the use of threefold symmetrically substituted triaminoguanidines as novel hosts in supramolecular chemistry or as ligands in coordination

• chemistry. Molecular structure of 6b·2C2H5OH in the solid state, with numbering of atoms (ORTEP plot). Selected bond lengths (Å): C1–N1 1.297(4), C1–C2 1.390(4), C1–N3 1.365(4). Selected bond angles (°): N1–C1–N2 117.3(3), N2–C1–N3 115.6(2), N1–C1–N3 126.9(3). Hydrogen bonds to the two ethanol molecules: N2

From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer

• Ming Liu,
• Jan C. Namyslo,
• Martin Nieger,
• Mika Polamo and
• Andreas Schmidt

Beilstein J. Org. Chem. 2016, 12, 2673–2681, doi:10.3762/bjoc.12.264

• ], versatile organocatalysts [8][9][10], and starting materials for heterocycle syntheses [11][12][13]. Consequently books [14][15][16] and reviews cover the range from NHC structures in the light of their early history [17], syntheses [6][18], coordination chemistry [19][20], and catalysis [21][22], to

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

• Artem N. Semakin,
• Aleksandr O. Kokuev,
• Yulia V. Nelyubina,
• Alexey Yu. Sukhorukov,
• Petr A. Zhmurov,
• Sema L. Ioffe and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

• polyhydrazones exhibit a rich coordination chemistry owing to a variety of binding modes and are widely employed as ligands in metal-organic assemblies, sensors and catalytic systems [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. More complex structures containing several hydrazone groups

• -, tris- and tetrahydrazone ligands were prepared. Trishydrazone 11b was shown to undergo an intramolecular cyclotrimerization of the C=N bonds resulting in the formation of the respective N-amino-substituted 1,4,6,10-tetraazaadamantane derivative. Further studies of coordination chemistry aspects of poly

A T-shape diphosphinoborane palladium(0) complex

• Patrick Steinhoff and
• Michael E. Tauchert

Beilstein J. Org. Chem. 2016, 12, 1573–1576, doi:10.3762/bjoc.12.152

• (CyDPBPh)Pd(0) 9, which was characterized by X-ray analysis. Keywords: ambiphilic ligand; coordination chemistry; diphosphinoborane; organometallics; palladium; Introduction The amplification of traditional bidentate chelating L2-type ligands with a tethered borane functionality (e.g., Bourissou’s

Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

• Shaojin Gu,
• Jiehao Du,
• Jingjing Huang,
• Huan Xia,
• Ling Yang,
• Weilin Xu and
• Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

• , the easy synthesis and versatile coordination ability of 1,2,3-triazoles have led to an explosion of interest in coordination chemistry [21] and homogeneous catalysis [22][23][24][25][26]. Although a number of metal complexes containing 1,4-disubstituted-1,2,3-triazole ligands were well studied

A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

• Vladislav Vasilenko,
• Torsten Roth,
• Clemens K. Blasius,
• Sebastian N. Intorp,
• Hubert Wadepohl and
• Lutz H. Gade

Beilstein J. Org. Chem. 2016, 12, 846–853, doi:10.3762/bjoc.12.83

• donors, with distinct consequences for their coordination chemistry (vide infra). Complex synthesis In the next step of our study we set out to explore the coordination chemistry and structural properties of the synthesized ligands with rhodium(I/III), iridium(I/III) and palladium(II) precursors

Creating molecular macrocycles for anion recognition

• Amar H. Flood

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

• bound metals, for example, Fe(II), Ru(II) and Eu(III) [11]. It was at this point that I lifted my head and asked the next critical questions: how are triazoles not the same as pyridines and what does the coordination chemistry teach us about how these 1,2,3-triazoles like to behave? All our observations

• the CH groups in pyridine that poke uncomfortably into neighboring ligands. The coordination chemistry taught us that triazoles are sterically small, perhaps small enough to be as innocent as ethynyl units (e.g., Figure 4d and overlay in Figure 4e). If that idea was true, then triazoles became prime

Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones

• Ping Qian,
• Bingnan Du,
• Wei Jiao,
• Haibo Mei,
• Jianlin Han and
• Yi Pan

Beilstein J. Org. Chem. 2016, 12, 301–308, doi:10.3762/bjoc.12.32

• Ping Qian Bingnan Du Wei Jiao Haibo Mei Jianlin Han Yi Pan School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China Institute for Chemistry & BioMedical Sciences, Nanjing University, Nanjing, 210093, China 10.3762

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

• Zhan-Jiang Zheng,
• Ding Wang,
• Zheng Xu and
• Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

• addition, the application of bitriazoles and the related CuAAAC reaction in different fields, including medicinal chemistry, coordination chemistry, biochemistry, and supramolecular chemistry, have been highlighted. Keywords: bistriazoles; click chemistry; cycloaddition; homogeneous catalysis; oxidative

Aerobic addition of secondary phosphine oxides to vinyl sulfides: a shortcut to 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides

• Svetlana F. Malysheva,
• Alexander V. Artem’ev,
• Nina K. Gusarova,
• Nataliya A. Belogorlova,
• Alexander I. Albanov,
• C. W. Liu and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2015, 11, 1985–1990, doi:10.3762/bjoc.11.214

• coordination chemistry [1][2][3][4]. Therefore, the synthesis of these compounds has attracted a great interest and numerous synthetic methods have been developed [5][6][7]. Among them, the addition of P(X)–H (X = none, O, S or Se) to diverse alkenes is one of the most powerful and 100% atom-economic

Synthesis and structures of ruthenium–NHC complexes and their catalysis in hydrogen transfer reaction

• Chao Chen,
• Chunxin Lu,
• Qing Zheng,
• Shengliang Ni,
• Min Zhang and
• Wanzhi Chen

Beilstein J. Org. Chem. 2015, 11, 1786–1795, doi:10.3762/bjoc.11.194

• ]. Among NHCs, functionalized NHC ligands have been extensively studied in recent years because of their intriguing structural diversities and potential applications in coordination chemistry and homogenous catalysis. NHC ligands containing additional phosphine, nitrogen, oxygen, and sulfur donating groups

Advances in the synthesis of functionalised pyrrolotetrathiafulvalenes

• Luke J. O’Driscoll,
• Sissel S. Andersen,
• Marta V. Solano,
• Dan Bendixen,
• Morten Jensen,
• Troels Duedal,
• Jess Lycoops,
• Cornelia van der Pol,
• Rebecca E. Sørensen,
• Karina R. Larsen,
• Kenneth Myntman,
• Christian Henriksen,
• Stinne W. Hansen and
• Jan O. Jeppesen

Beilstein J. Org. Chem. 2015, 11, 1112–1122, doi:10.3762/bjoc.11.125

• molecular machines [1][2][3][4][5], molecular and organic electronics [5][6][7], chemosensors [1][8][9][10][11], coordination chemistry [12][13][14], catalysis [15] and beyond [16][17][18][19][20][21]. This owes much to the strong electron-donor character of the TTF moiety and its derivatives, which have

Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively

• Marcel Mirel Popa,
• Emilian Georgescu,
• Mino R. Caira,
• Florentina Georgescu,
• Constantin Draghici,
• Raluca Stan,
• Calin Deleanu and
• Florea Dumitrascu

Beilstein J. Org. Chem. 2015, 11, 1079–1088, doi:10.3762/bjoc.11.121

• chemistry of 4-(2-pyridyl)pyrimidine (6) is rather scarce compared to its structural 2,2’-bipyridyl analogue but should raise interest for similar synthetic applicative purposes. Also the isomers of 6, compounds 7 and 8, are of interest for coordination chemistry both as ligands and as bridging compounds

CO₂ Chemistry

• Thomas E. Müller and
• Walter Leitner

Beilstein J. Org. Chem. 2015, 11, 675–677, doi:10.3762/bjoc.11.76

• overcome its thermodynamically low level, additional energy is required to activate the CO2 molecule. The threefold reactivity (Figure 3) of CO2 with a nucleophilic oxygen atom, an electrophilic carbon atom and a π system provides the chemist with many options. Likewise, a rich coordination chemistry to

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

Second generation silver(I)-mediated imidazole base pairs

• Susanne Hensel,
• Nicole Megger,
• Kristina Schweizer and
• Jens Müller

Beilstein J. Org. Chem. 2014, 10, 2139–2144, doi:10.3762/bjoc.10.221

• increased charge transfer capability [10][11] and DNA-based logic gates [12][13]. Applying the concepts of coordination chemistry, a wide range of metal-specific ligands have been incorporated successfully into nucleic acids and nucleic acid derivatives. Most recently, even coordination patterns of the [2

Macrocyclic bis(ureas) as ligands for anion complexation

• Claudia Kretschmer,
• Gertrud Dittmann and
• Johannes Beck

Beilstein J. Org. Chem. 2014, 10, 1834–1839, doi:10.3762/bjoc.10.193

• molecule” – is an area of modern chemistry, which has grown exponentially in the last decades [1][2]. Among the many concepts of supramolecular interactions, anion coordination chemistry has always been an intensively explored field, which still offers substantial progress [3][4][5]. The urea group has