Controlled decomposition of SF₆ by electrochemical reduction

• Sébastien Bouvet,
• Bruce Pégot,
• Stéphane Sengmany,
• Erwan Le Gall,
• Eric Léonel,
• Anne-Marie Goncalves and
• Emmanuel Magnier

Beilstein J. Org. Chem. 2020, 16, 2948–2953, doi:10.3762/bjoc.16.244

• macroelectrodes, the current density on microelectrodes is very high. This allows a better current sensitivity in electrochemical measurements (cyclic voltametrics, polarization curve …) providing the study of rapid electron and coupled chemical reactions. In comparison to macroelectrodes, their small size leads

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• unprecedented attention to photochemistry [70][71]. Increasing interest in photochemistry is often attributed to the ability to access radical intermediates that are otherwise difficult or impossible to obtain by classical chemistry but that can achieve unique chemical reactions complementary to two-electron

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

• Alberto Rubin Pedrazzo,
• Fabrizio Caldera,
• Marco Zanetti,
• Silvia Lucia Appleton,
• Nilesh Kumar Dhakar and
• Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

• drive and control chemical reactions, for example, using grinding or milling to transfer energy to chemical bonds [11]. Mechanochemical transformations are well established in inorganic chemistry and they are easily transferable to an industrial scale [12][13]. Mechanochemistry in organic chemistry

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• emissions and subsequent environmental damage, much of the scientific community has shifted its focus to the development of sustainable methodologies, particularly in synthetic chemistry. The prospect of utilising light as a renewable source of energy to drive chemical reactions is an appealing solution to

• topic in 2019 alone (Figure 1A). The credit for the development of this field is often given to MacMillan [24], Yoon [25], and Stephenson [26], whose seminal papers in 2008 and 2009 elegantly demonstrated the photocatalytic ability of ruthenium–bipyridyl complexes to drive chemical reactions with

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

• Mateo Berton,
• Kevin Sheehan,
• Andrea Adamo and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2020, 16, 1343–1356, doi:10.3762/bjoc.16.115

• system photos, and ODR prototype protocols) and all experimental data of the chemical reactions (optimization, packed-bed particle size study, and concentration determination) and NMR spectra. Supporting Information File 58: Additional experimental data. Acknowledgements We thank Bernat Moreno (https

Aldehydes as powerful initiators for photochemical transformations

• Maria A. Theodoropoulou,
• Nikolaos F. Nikitas and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2020, 16, 833–857, doi:10.3762/bjoc.16.76

• are useful photocatalysts, the corresponding aldehydes are not so widely utilized to promote chemical reactions. In this review, our goal was to summarize the photophysical properties of aromatic aldehydes, highlight the use of aldehydes as photoinitiators in polymerization reactions, and provide all

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

• Bernd Strehmel,
• Christian Schmitz,
• Ceren Kütahya,
• Yulian Pang,
• Anke Drewitz and
• Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

• charge typically distributes over the entire conjugated system. There are much more valence patterns possible to draw. For a sake of simplicity, we operate with one feasible structure. The availability of these precursors bases on easy pursuable chemical reactions resulting in huge libraries of cyanines

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

• Lorenzo Sansalone,
• Jun Zhao,
• Matthew T. Richers and
• Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

• ) UPLC chromatograms of chemical reactions shown in (a). Elution 0.75 to 1 mL/min, 2–100% acetonitrile in water for 4 min. Testing photo-antagonism of 1 with genetically tagged nicotinic acetylcholine receptors. Currents from HEK293 cells were measured using the whole-cell patch-clamp method. Cell were

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

• Vânia F. Pais,
• Tristan Neumann,
• Ignacio Vayá,
• M. Consuelo Jiménez,
• Abel Ros and
• Uwe Pischel

Beilstein J. Org. Chem. 2019, 15, 2612–2622, doi:10.3762/bjoc.15.254

• reference. 11B NMR spectra were recorded with complete proton decoupling at 160 MHz, using BF3·Et2O (0.00 ppm for 11B NMR) as standard. All chemical reactions were carried out in oven-dried Schlenk tubes under an argon atmosphere. Toluene, 1,4-dioxane, and methanol were purchased from Carlo Erba and were

Reversible switching of arylazopyrazole within a metal–organic cage

• Anton I. Hanopolskyi,
• Soumen De,
• Michał J. Białek,
• Yael Diskin-Posner,
• Liat Avram,
• Moran Feller and
• Rafal Klajn

Beilstein J. Org. Chem. 2019, 15, 2398–2407, doi:10.3762/bjoc.15.232

• ; photochromism; Introduction The importance of confinement for chemical reactivity is becoming increasingly appreciated. Confining reactive species to small volumes can greatly increase their effective molarity and consequently, promote chemical reactions. Such reaction acceleration has been demonstrated at

• interfaces [1][2][3], in self-assembled cages [4][5][6][7], on DNA chains [8], and on the surfaces of inorganic nanoparticles [9][10]. Additionally, nanosized cages can induce preorganization of the encapsulated species, thus inducing unusual regioselectivities in various chemical reactions [11][12][13]. The

Isolation and characterisation of irinans, androstane-type withanolides from Physalis peruviana L.

• Annika Stein,
• Dave Compera,
• Bianka Karge,
• Mark Brönstrup and
• Jakob Franke

Beilstein J. Org. Chem. 2019, 15, 2003–2012, doi:10.3762/bjoc.15.196

• irinans, from Physalis peruviana with highly unusual truncated backbones that resemble mammalian androstane sex hormones. Based on biomimetic chemical reactions, we propose a model that links these compounds to withanolide biosynthesis. Irinans have potent antiproliferative activities, that are however

Understanding the unexpected effect of frequency on the kinetics of a covalent reaction under ball-milling conditions

• Ana M. Belenguer,
• Adam A. L. Michalchuk,
• Giulio I. Lampronti and
• Jeremy K. M. Sanders

Beilstein J. Org. Chem. 2019, 15, 1226–1235, doi:10.3762/bjoc.15.120

• for a wide range of different syntheses and chemical reactions of inorganic [8][9] and organic [10][11] compounds. Even supramolecular architectures such as co-crystals and metal-organic frameworks [4][12][13][14], cages [15] and rotaxanes [16] could be formed mechanochemically. Crucially, the

• their dependence on the milling frequency. Furthermore, they each exhibit sizeable induction periods, far greater than most reported kinetic profiles of multi-phase mechanochemical non-covalent supramolecular chemical reactions [28][45]. The notable exceptions are similar synthetic reactions, which

Mechanochemical amorphization of chitin: impact of apparatus material on performance and contamination

• Thomas Di Nardo and
• Audrey Moores

Beilstein J. Org. Chem. 2019, 15, 1217–1225, doi:10.3762/bjoc.15.119

• , with the specific reaction kinetic parameters [33]. There is, however, an interest in investigating these aspects further. In particular, it would be interesting to track the role of parameters such as ball size and mass on the progress of the reaction. In mechanochemistry, it is accepted that chemical

• reactions are induced by the delivery of energy, by collision. The impact force is thus of importance and depends on the weight of the balls and [26] the surface of impact [28]. Also, in the context of the milling of crystalline and/or fairly hard materials, the nature of the milling media composing the

Mechanochemical synthesis of poly(trimethylene carbonate)s: an example of rate acceleration

• Sora Park and
• Jeung Gon Kim

Beilstein J. Org. Chem. 2019, 15, 963–970, doi:10.3762/bjoc.15.93

• carbonate); Introduction Nowadays mechanochemical syntheses are widespread in many areas of chemistry [1][2][3][4]. The efficient mixing and energy input induced by mechanical motions have promoted many chemical reactions with superior efficiencies [5]. Sometimes, unexpected outcomes that cannot be

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• in life phenomena [47][48][49][50][51][52][53][54] and of promoting site-selective chemical reactions such as polymerization. Very recently, Guillaneuf and co-workers reported the two-photon-induced release of nitroxides in a materials science study [55]. In the last decade, we developed a TP

Low-budget 3D-printed equipment for continuous flow reactions

• Jochen M. Neumaier,
• Amiera Madani,
• Thomas Klein and
• Thomas Ziegler

Beilstein J. Org. Chem. 2019, 15, 558–566, doi:10.3762/bjoc.15.50

• of the chemical reactions and NMR spectra. Supporting Information File 204: This zip-file includes all 3D-printed parts as stl-files for direct 3D printing, as well as stp-files for editing the 3D models, if necessary. It also contains the Arduino software code as an ino-file for controlling of the

Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

• Mikhail V. Makarov and
• Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

• stable in pyridine even at room temperature suffering transformations into the corresponding quaternary pyridine ribofuranoside [20]. These observations highlight the need for special appreciations for the chemical stability of the glycosidic bond in NR+ when conducting chemical reactions and choosing

Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation

• Łukasz Gułajski,
• Andrzej Tracz,
• Katarzyna Urbaniak,
• Stefan J. Czarnocki,
• Michał Bieniek and
• Tomasz K. Olszewski

Beilstein J. Org. Chem. 2019, 15, 160–166, doi:10.3762/bjoc.15.16

• interesting transformation. Furthermore, in the continuous search for new sustainable protocols for chemical reactions to induce new reactivates or reduce the energetic cost of the processes, the replacement of mechanical mixing and/or heating of the reacting species with microwave (μW) [46][47][48] and

N-Arylphenothiazines as strong donors for photoredox catalysis – pushing the frontiers of nucleophilic addition of alcohols to alkenes

• Fabienne Speck,
• David Rombach and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 52–59, doi:10.3762/bjoc.15.5

• applications. The access to electronically excited states of organic molecules allows unlocking new and sometimes complementary chemical reactivities that cannot be tackled by using thermally driven chemical reactions [1]. This complementarity allows for the development of so far unknown transformations [2

• processes. Conclusion One of the major current challenges in photoredox catalysis is the design of chromophores suitable for the most reductive chemical reactions, like for instance reductions by alkaline metals, affording reaction conditions that are easier to handle. While solid sodium comes up with a

Dispersion interactions

• Peter R. Schreiner

Beilstein J. Org. Chem. 2018, 14, 3076–3077, doi:10.3762/bjoc.14.286

• ) approaches largely lacked the inclusion of LD. The often very good results of standard DFT implementations in the description of chemical reactions can in part be traced back to the compensating effects of neglecting both dispersion and solvation. This is not to say that dispersion vanishes [7] in solution

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• increasingly turned to it as the greenest solvent of chemical reactions [34]. In order to find the best reaction conditions, a model reaction was chosen using (L)-alanine phenylhydrazide (3a, Scheme 3), and the results of these optimized studies were summarized in Table 2. The best result was obtained when a

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• commercial strong acids with pKa-values of −1.9 and −2.8, respectively, which are regularly used as simplest and more usable catalysts in chemical reactions. MSA is almost completely ionized at a concentration of 0.1 M in an aqueous solution. The oxidative stability of organic compounds and metal ions in MSA

• -flammability, low volatility, and safety. These eco-friendly materials have been applied as a new category of catalysts in some organic reactions as well. Recently, new sulfonated ionic liquids and sulfonated solid salts have been prepared and used as efficient catalysts in various chemical reactions [35][36

Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains

• Jiang Liu,
• Peter Leonard,
• Sebastian L. Müller,
• Constantin Daniliuc and
• Frank Seela

Beilstein J. Org. Chem. 2018, 14, 2404–2410, doi:10.3762/bjoc.14.217

• . Monomeric purine and pyrimidine nucleosides form smaller ring systems known as cyclonucleosides incorporating O, N or S-bridges within the sugar moiety or between the nucleobase and the sugar residue [6]. Macrocycles can be obtained by a variety of chemical reactions [7][8][9][10]. Often, several protection

The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX

• Md Toufique Alam,
• Saikat Maiti and
• Prasenjit Mal

Beilstein J. Org. Chem. 2018, 14, 2396–2403, doi:10.3762/bjoc.14.216

• using several arylamines and hypervalent iodine(V) reagents by direct mixing is unrealistic because of the high exothermic reaction or explosion. Herein we demonstrate, when anilines were substituted with an amide group at the ortho-position, successful chemical reactions could be performed due to

Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I

• Pamarthi Gangadhar,
• Sayini Ramakrishna,
• Ponneri Venkateswarlu and
• Pabbaraja Srihari

Beilstein J. Org. Chem. 2018, 14, 2313–2320, doi:10.3762/bjoc.14.206

• Okinawan marine sponge of the genus Petrosia (Strongylophora). The structural elucidation was accomplished by spectroscopic analyses and chemical reactions. It was found that these strongylodiols were present as an enantiomeric mixture with different ratios after analysis of their corresponding MNA ((R