Synthesis and characterization of bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives

• David Martínez-López,
• Amirhossein Babalhavaeji,
• Diego Sampedro and
• G. Andrew Woolley

Beilstein J. Org. Chem. 2019, 15, 3000–3008, doi:10.3762/bjoc.15.296

• PerkinElmer Series 200 pump with a Waters 2487 Dual λ Absorbance Detector connected to an eDAQ PowerChrom 280 recorder. One-dimensional 1H and 13C NMR spectra were recorded on a Varian UnityPlus 500 MHz or Varian Mercury 400 MHz spectrometer. Chemical shifts are reported in ppm, and the signals were

Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles

• Hoang Huy Do,
• Saif Ullah,
• Alexander Villinger,
• Joanna Lecka,
• Jean Sévigny,
• Peter Ehlers,
• Jamshed Iqbal and
• Peter Langer

Beilstein J. Org. Chem. 2019, 15, 2830–2839, doi:10.3762/bjoc.15.276

• = 254 nm). Column chromatography was performed on Fluka silica gel 60 (0.063–0.200 mm, 70–320 mesh) on a glass column. For the cation exchange column dowex 50WX8 H+ was used. Melting points (mp) were determined by the instrument Elektrothermal. 1H and 13C NMR spectra («Mercury-300 Varian» 300 MHz with

Iodine-mediated hydration of alkynes on keto-functionalized scaffolds: mechanistic insight and the regiospecific hydration of internal alkynes

• Zachary Lee,
• Brandon R. Jones,
• Nyochembeng Nkengbeza,
• Michael Phillips,
• Kayla Valentine,
• Alexis Stewart,
• Brandon Sellers,
• Nicholas Shuber and
• Karelle S. Aiken

Beilstein J. Org. Chem. 2019, 15, 2747–2752, doi:10.3762/bjoc.15.265

• ; regiospecific hydration; Findings The Kucherov reaction is one of the most well-known approaches for the hydration of alkynes. This reaction, originally published in 1881, requires the use of mercury(II) salts in catalytic quantities [1][2]. Countless studies have shown that mercury-based compounds are

• (II) [7], silver(I) [8], and gold(I)/(III) [9][10][11][12]. While less toxic than mercury, such catalysts are still environmental hazards and tend to be costlier [13][14]. The iodine-mediated hydration described herein is a viable solution to these issues [15][16]. This metal-free method produces

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• by Wattanakit described several approaches for the development of chiral metal electrodes for enantioselective recognition and asymmetric synthesis developed over the past decade [18]. Concurrent with pioneering works in the field of asymmetric induction in electrochemical reduction on chiral mercury

• mixture during the electroreduction of acetophenone on a mercury cathode induces optical activity in the product (alcohol 24a, Scheme 7) [29]. Additionally, pinacol (23) was also obtained via dimerization along with chiral alcohols. The same method was reinvestigated by Wang and Lu in 2013 using a silver

• , conditions B). Based on a strychnine alkaloid-induced asymmetric electroreduction, Kopilov, Kariv and Miller showed that 4- and 2-acetylpyridines (1 and 25) could be reduced to the corresponding pyridylethanols (2 and 26, respectively) in presence of a catalytic amount of the alkaloid on a mercury cathode

Experimental and computational electrochemistry of quinazolinespirohexadienone molecular switches – differential electrochromic vs photochromic behavior

• Eric W. Webb,
• Jonathan P. Moerdyk,
• Kyndra B. Sluiter,
• Benjamin J. Pollock,
• Amy L. Speelman,
• Eugene J. Lynch,
• William F. Polik and
• Jason G. Gillmore

Beilstein J. Org. Chem. 2019, 15, 2473–2485, doi:10.3762/bjoc.15.240

• chemical oxidant (benzoquinone) added to complete the reduction of the dianion to the LW isomer. NMR spectroscopy was performed on samples 5 mm NMR tubes (Wilmad) made of clear quartz (photolyzed samples) or amber pyrex (dark samples) on a Varian Mercury or Bruker AvanceIII 400 MHz NMR. 1H NMR experiments

Effect of ring size on photoisomerization properties of stiff stilbene macrocycles

• Sandra Olsson,
• Óscar Benito Pérez,
• Magnus Blom and
• Adolf Gogoll

Beilstein J. Org. Chem. 2019, 15, 2408–2418, doi:10.3762/bjoc.15.233

• system. 1H and 13C NMR spectra were recorded on Varian Mercury Plus (1H at 300.03 MHz), Agilent 400-MR DD2 (1H at 399.98 MHz, 13C at 100.58 MHz), Varian Unity Inova (1H at 499.94 MHz) and Bruker Avance Neo (1H at 500.15 MHz, 13C at 125.78 MHz) spectrometers at 25 °C. Chemical shifts (δ) are reported in

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

• András György Németh,
• György Miklós Keserű and
• Péter Ábrányi-Balogh

Beilstein J. Org. Chem. 2019, 15, 1523–1533, doi:10.3762/bjoc.15.155

• as enzyme inhibitors [26] or antitumor agents [27]. These species are also used as valuable synthetic intermediates [28] and chemosensors for mercury and silver [29][30]. The general methods for the synthesis of O-thiocarbamates and dithiocarbamates traditionally rely on substitution reactions of the

Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

• Andrew T. King,
• Hugh G. Hiscocks,
• Lidia Matesic,
• Mohan Bhadbhade,
• Roger Bishop and
• Alison T. Ung

Beilstein J. Org. Chem. 2019, 15, 1347–1354, doi:10.3762/bjoc.15.134

• refinements were carried out using SHELXL-2014 [35] through Olex2 [36] suite of software. The non-hydrogen atoms were refined anisotropically. Molecular graphics were generated using Mercury [37]. Key crystallographic data and refinement details are presented in Table 1. Crystal structure data

Insertion of [1.1.1]propellane into aromatic disulfides

• Robin M. Bär,
• Gregor Heinrich,
• Martin Nieger,
• Olaf Fuhr and
• Stefan Bräse

Beilstein J. Org. Chem. 2019, 15, 1172–1180, doi:10.3762/bjoc.15.114

• , the conversion could be accelerated in the beginning of the measurement. However, after the work-up of the reaction with radical initiator, an insoluble white solid, presumably longer [n]staffanes, was discovered. When the reaction was performed in a 500 W UV reactor (medium-pressure mercury-vapor

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• Specord M-82 spectrometer. The 1H NMR spectra were measured on a Varian Mercury VX-200 (200 MHz) and Bruker AM-400 spectrometer (400 MHz), 13C NMR spectra were measured on a Bruker AM-400 (100 MHz) and Bruker Avance DRX 500 (125 МHz) spectrometers in DMSO-d6, CDCl3 and trifluoroacetic acid (TFA) using TMS

Thiol-free chemoenzymatic synthesis of β-ketosulfides

• Adrián A. Heredia,
• Martín G. López-Vidal,
• Marcela Kurina-Sanz,
• Fabricio R. Bisogno and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2019, 15, 378–387, doi:10.3762/bjoc.15.34

• thiols (Scheme 1) [17][18][19][20][21], other methodologies employing different sulfur sources such as disulfides or silylsulfides have been described, which most of them involves metals, e.g., indium [22], copper [23], mercury [24], or organocatalysts [25]. β-Ketosulfides, in addition, play an important

Carbonylonium ions: the onium ions of the carbonyl group

• Daniel Blanco-Ania and
• Floris P. J. T. Rutjes

Beilstein J. Org. Chem. 2018, 14, 2568–2571, doi:10.3762/bjoc.14.233

• group with mercury to a double bond. “Oxycarbenium ion” can also be found in the literature with this meaning that it correctly describes the same intermediate, although not the more realistic representation of it [30]. Carboxonium ions Other research groups, e.g., Olah’s and Prakash’s, have used the

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

• Femke Beiroth,
• Tomas Koudelka,
• Thorsten Overath,
• Stefan D. Knight,
• Andreas Tholey and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

• . Subsequently, the solution was irradiated under ice cooling with a medium pressure mercury vapor lamp for 10 min. Afterwards, 50 µL double distilled water were added and 2 µL of this solution given to 20 µL of a 0.1% trifluoroacetic acid (TFA) solution, desalted with a C18 µZipTip and spotted on a MALDI-plate

• in ACN or DMSO. The ratio ligand to protein was 70:1. The total volume of the reaction was 11 µL either with 50% ACN or 10% DMSO. Ligand and protein were combined and incubated for 10 min at 37 °C and 100 rpm. Afterwards the solution was irradiated under ice cooling with a medium pressure mercury

Water-soluble SNS cationic palladium(II) complexes and their Suzuki–Miyaura cross-coupling reactions in aqueous medium

• Alphonse Fiebor,
• Richard Tia,
• Banothile C. E. Makhubela and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1859–1870, doi:10.3762/bjoc.14.160

• mixture turned black in the presence of TBAB, we were under the impression that the reaction could have proceeded via formation of palladium nanoparticles as it is common with most palladium catalysed coupling reactions. However, mercury drop experiments provided comparable yields (Table 2, entry 29 and

• 30) under the same reaction conditions ruling out the possibility of a coupling reaction catalysed by palladium nanoparticles [37]. The fact that the reaction mixture remained yellowish in the absence of TBAB and the mercury drop experiments did not lead to an appreciable decrease in yield, the

• ), alkylphosphine (PCP) and aminophosphine (PCP) pincer complexes, and in each of these cases, catalysis was unaffected by metallic mercury during the cross-coupling reactions [41][42][43]. In addition, stable Pd(IV) complexes have been widely prepared and characterised, thus for the catalysis of the pincer

Anomeric modification of carbohydrates using the Mitsunobu reaction

• Julia Hain,
• Patrick Rollin,
• Werner Klaffke and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

• ]. Stereoselective β-D-mannoside synthesis [60]. TIPS-assisted synthesis of 1,2-cis arabinofuranosides [63]. TIPS: triisopropylsilyl. The Mitsunobu reaction with glycals leads to interesting rearrangement products [69]. Synthesis of disaccharides using mercury(II) bromide as co-activator in the Mitsunobu reaction

Spectroelectrochemical studies on the effect of cations in the alkaline glycerol oxidation reaction over carbon nanotube-supported Pd nanoparticles

• Dennis Hiltrop,
• Steffen Cychy,
• Karina Elumeeva,
• Wolfgang Schuhmann and
• Martin Muhler

Beilstein J. Org. Chem. 2018, 14, 1428–1435, doi:10.3762/bjoc.14.120

• layer configuration, where the thickness of the thin layer is tunable in the micrometer range by an implemented micrometer screw. The Bruker Tensor 27 FTIR spectrometer was equipped with an A530/P reflection unit, a liquid nitrogen mercury cadmium telluride detector and was constantly purged with dried

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

• of catalytic mercury iodide; it is a critical step for the formation of the compound 72. Hydrolysis of intermediate 68 led to ketone 69 in high yield containing an acetic acid residue β to the carbonyl group. A sequence of the one-carbon homologation of ketone 69 is followed by isomerization into the

Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

• Toshifumi Dohi,
• Shohei Ueda,
• Kosuke Iwasaki,
• Yusuke Tsunoda,
• Koji Morimoto and
• Yasuyuki Kita

Beilstein J. Org. Chem. 2018, 14, 1087–1094, doi:10.3762/bjoc.14.94

• replacement for certain heavy-metal oxidizers, such as lead, mercury, and thallium-based salts, due to their low toxicities, high stabilities, operational simplicities, and many other user-friendly characteristics [31][32]. By virtue of their wide array of reactivity patterns, the controllable radical and

2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

• Takayuki Yakura,
• Tomoya Fujiwara,
• Akihiro Yamada and
• Hisanori Nambu

Beilstein J. Org. Chem. 2018, 14, 971–978, doi:10.3762/bjoc.14.82

• fundamental and frequently used transformation in organic synthesis. Heavy metal-based oxidants such as chromium(VI), lead(IV), and mercury(II) have been extensively used for this purpose for a long time. However, these oxidants are highly toxic and produce hazardous waste. Recently, hypervalent iodine

Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies

• Elias Christoforides,
• Andreas Papaioannou and
• Kostas Bethanis

Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69

• the host molecules. The graphic programs used to illustrate the crystal structures are Mercury 3.9 [43] and Olex2 [44]. Selected details of structure refinement along with important statistics are given in Table 1. The data can be obtained from The Cambridge Crystallographic Data Centre under the

• cholesterol molecule; (b) the β-cyclodextrin molecule. (a) Crystal structure of the inclusion compound of cholesterol in β-CD dimer. Water molecules are omitted for clarity. (b) The inclusion complex colored by atomic displacement parameters (U’s) using Mercury 3.9. The values of U increase from blue to red

Synthesis of fluoro-functionalized diaryl-λ³-iodonium salts and their cytotoxicity against human lymphoma U937 cells

• Prajwalita Das,
• Etsuko Tokunaga,
• Hidehiko Akiyama,
• Hiroki Doi,
• Norimichi Saito and
• Norio Shibata

Beilstein J. Org. Chem. 2018, 14, 364–372, doi:10.3762/bjoc.14.24

• neutral size 63–210 μm). The 1H NMR (300 MHz), 19F NMR (282 MHz), and 13C NMR (125 MHz) spectra for solution in CDCl3 or (CD3)2CO were recorded on Varian Mercury 300 and Bruker Avance 500 spectrometers. Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00) or C6F6 [δ = −162.2 (CDCl3) or

Halogen-containing thiazole orange analogues – new fluorogenic DNA stains

• Aleksey A. Vasilev,
• Meglena I. Kandinska,
• Stanimir S. Stoyanov,
• Stanislava B. Yordanova,
• David Sucunza,
• Juan J. Vaquero,
• Obis D. Castaño,
• Stanislav Baluschev and
• Silvia E. Angelova

Beilstein J. Org. Chem. 2017, 13, 2902–2914, doi:10.3762/bjoc.13.283

• spectra and is in contrast to the by Armitage et al. observed influence of the replacement of hydrogen with fluorine atom in the benzothiazole ring [43]. Photostability The photostability of all dyes in the series was evaluated in acetonitrile with irradiation at 254 nm with a mercury lamp in equal

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• Uiso(H) = xUeq(C), where x = 1.2 for the aromatic, methylene and methine H atoms, and x = 1.5 for the methyl H atoms. All presented molecular interactions were found using the PLATON program [44]. The figures for this publication were prepared using ORTEP-3 and Mercury programs [45][46]. The CCDC

Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity

• Tathagata Mukherjee,
• Soumik Biswas,
• Andreas Ehnbom,
• Subrata K. Ghosh,
• Ibrahim El-Zoghbi,
• Nattamai Bhuvanesh,
• Hassan S. Bazzi and
• John A. Gladysz

Beilstein J. Org. Chem. 2017, 13, 2486–2501, doi:10.3762/bjoc.13.246

• the solvents, starting materials, and instrumentation employed, and additional spectroscopic, structural, and computational data, including a molecular structure file that can be read by the program Mercury [75] and contains the optimized geometries of all computed structures [76]. Supporting

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• , 0.70/0.30 in 6, and 0.68/0.32 in 7. Geometric restraint on some of the C–F distances and restraint on anisotropic displacement parameters of some fluorine atoms in 5–8 were applied in the refinement. The PLATON [62] and Mercury [63] programs were used for structure analysis and molecular and crystal