Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

• Pablo Quijano Velasco,
• Kedar Hippalgaonkar and
• Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

• chemical reactions. In the current review, we focus on the high-throughput data processing that complements the HTE platforms for rapid optimization of organic reactions. Although multivariate data analysis has frequently been adopted in analytical chemistry for rapid data processing, the availability of

Surprising acidity for the methylene of 1,3-indenocorannulenes?

• Shi Liu,
• Märt Lõkov,
• Sofja Tshepelevitsh,
• Ivo Leito,
• Kim K. Baldridge and
• Jay S. Siegel

Beilstein J. Org. Chem. 2024, 20, 3144–3150, doi:10.3762/bjoc.20.260

• Analytical Chemistry (TT4, https://www.akki.ee) and was supported by the Estonian Research Council grant (PRG690) and by the Estonian Ministry of Education and Research (TK210).

Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ³-iodanes

• Thomas J. Kuczmera,
• Pim Puylaert and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 1677–1683, doi:10.3762/bjoc.20.149

• Thomas J. Kuczmera Pim Puylaert Boris J. Nachtsheim Institute for Organic and Analytical Chemistry, University of Bremen, Bremen, Germany Institute for Inorganic Chemistry and Crystallography, University of Bremen, Bremen, Germany 10.3762/bjoc.20.149 Abstract We present N-heterocycle-stabilized

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

• Fátima C. Teixeira,
• António P. S. Teixeira and
• C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

• combinatorial chemistry [35], in analytical chemistry, in electrochemical redox processes, in crystal engineering, and as fluorescent, light emitting, corrosion inhibitors or several other materials [36][37][38][39][40][41][42]. The most used triazine is 1,3,5-triazine (or s-triazine) that can provide

Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide

• Christopher Mairhofer,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1510–1517, doi:10.3762/bjoc.20.135

• details and copies of NMR spectra. Acknowledgements We are grateful to Prof. Dr. Himmelsbach (Institute of Analytical Chemistry, JKU Linz) for support with HRMS analysis and Anna-Malin Draxler (Institute of Org. Chemistry, JKU Linz) for experimental support. Funding The used NMR spectrometers were

Towards an asymmetric β-selective addition of azlactones to allenoates

• Behzad Nasiri,
• Ghaffar Pasdar,
• Paul Zebrowski,
• Katharina Röser,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1504–1509, doi:10.3762/bjoc.20.134

• to allenoate 3aa. Supporting Information Supporting Information File 20: Full experimental and analytical details and copies of NMR spectra and HPLC traces. Acknowledgements We are grateful to Prof. Dr. Himmelsbach (Institute of Analytical Chemistry, JKU Linz) for support with HRMS analysis

Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts

• Nils Clamor,
• Mattis Damrath,
• Thomas J. Kuczmera,
• Daniel Duvinage and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 12–16, doi:10.3762/bjoc.20.2

• Nils Clamor Mattis Damrath Thomas J. Kuczmera Daniel Duvinage Boris J. Nachtsheim Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Straße 7, D-28359 Bremen, Germany Institute for Inorganic and Crystallographic Chemistry, University of Bremen, Leobener Straße 7, 28359

GlAIcomics: a deep neural network classifier for spectroscopy-augmented mass spectrometric glycans data

• Thomas Barillot,
• Baptiste Schindler,
• Baptiste Moge,
• Elisa Fadda,
• Franck Lépine and
• Isabelle Compagnon

Beilstein J. Org. Chem. 2023, 19, 1825–1831, doi:10.3762/bjoc.19.134

• anomericity). In this context, designing generic carbohydrate sequencing methods is both a major scientific challenge and a strategic priority [2][3]. Few years ago we proposed an original solution by bringing together the best of both sides of the analytical chemistry world: Spectroscopy and mass

• the few misclassification events in the discussion above. In order to address these points, we further assessed the precision of the model and discussed its epistemic uncertainty in the next section. Model precision and uncertainty In the context of analytical chemistry where the fraction of "known

New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones

• Vladislav Yu. Shuvalov,
• Ekaterina Yu. Vlasova,
• Tatyana Yu. Zheleznova and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2023, 19, 1155–1160, doi:10.3762/bjoc.19.83

• Vladislav Yu. Shuvalov Ekaterina Yu. Vlasova Tatyana Yu. Zheleznova Alexander S. Fisyuk Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave., 644050 Omsk, Russian Federation Department of Organic and Analytical Chemistry, F. M. Dostoevsky Omsk State University, Mira

Synthesis and reactivity of azole-based iodazinium salts

• Thomas J. Kuczmera,
• Annalena Dietz,
• Andreas Boelke and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 317–324, doi:10.3762/bjoc.19.27

• Thomas J. Kuczmera Annalena Dietz Andreas Boelke Boris J. Nachtsheim Institute for Organic and Analytical Chemistry, University of Bremen, 28359 Bremen, Germany 10.3762/bjoc.19.27 Abstract A systematic investigation of imidazo- and pyrazoloiodazinium salts is presented. Besides a robust synthetic

Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

• Julian Spils,
• Thomas Wirth and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 27–32, doi:10.3762/bjoc.19.2

• Julian Spils Thomas Wirth Boris J. Nachtsheim Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Straße 7, 28359 Bremen, Germany School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff CF10 3AT, UK 10.3762/bjoc.19.2 Abstract We describe a multi-step

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

• Attila Palágyi,
• Jindřich Jindřich,
• Juraj Dian and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

• , Prague 2, Czech Republic Department of Analytical Chemistry, Faculty of Science, Charles University, Hlavova 8, CZ-128 43, Prague, Czech Republic Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV), UR 4492 SFR Condorcet FR CNRS 3417, Université du Littoral-Côte d'Opale (ULCO

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

• Jamshid Amiri Moghaddam,
• Huijuan Guo,
• Karsten Willing,
• Thomas Wichard and
• Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

• Product Research and Infection Biology e.V., Hans-Knöll-Institute, Beutenbergstraße 11a, 07745 Jena, Germany Institute for Inorganic and Analytical Chemistry, Friedrich Schiller University Jena, Lessingstr 8, 07743 Jena, Germany Biochemistry of Microbial Metabolism, Institute of Biochemistry, Leipzig

N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts

• Viera Poláčková,
• Dominika Krištofíková,
• Boglárka Némethová,
• Renata Górová,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2021, 17, 2629–2641, doi:10.3762/bjoc.17.176

• Viera Polackova Dominika Kristofikova Boglarka Nemethova Renata Gorova Maria Meciarova Radovan Sebesta Department of Organic Chemistry,Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia Department of Analytical Chemistry

Icilio Guareschi and his amazing “1897 reaction”

• Gian Cesare Tron,
• Alberto Minassi,
• Giovanni Sorba,
• Mara Fausone and
• Giovanni Appendino

Beilstein J. Org. Chem. 2021, 17, 1335–1351, doi:10.3762/bjoc.17.93

• physiologist Moritz Schiff (1823–1892), who was already teaching in Florence [14]. After graduation, Guareschi returned to the University of Bologna as a lecturer of analytical chemistry in the group of Francesco Selmi (1817–1881), one of the founders of colloid chemistry and the initiator of the studies on

• contributions to the area are in the realm of analytical chemistry and in the systematic organization of the topic. In the course of these studies, Guareschi also isolated succinic acid from meat, the first report of this Krebs cycle intermediate from muscle tissues. The monograph on ptomaines [31] that

A new glance at the chemosphere of macroalgal–bacterial interactions: In situ profiling of metabolites in symbiosis by mass spectrometry

• Marine Vallet,
• Filip Kaftan,
• Veit Grabe,
• Fatemeh Ghaderiardakani,
• Simona Fenizia,
• Aleš Svatoš,
• Georg Pohnert and
• Thomas Wichard

Beilstein J. Org. Chem. 2021, 17, 1313–1322, doi:10.3762/bjoc.17.91

• Chemical Ecology, Jena, Germany Research Group Olfactory Coding, Department of Evolutionary Neuroethology, Max Planck Institute for Chemical Ecology, Jena, Germany Institute for Inorganic and Analytical Chemistry, Friedrich Schiller University Jena, Germany Max Planck Institute for Chemical Ecology, Jena

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

• David Weinzierl and
• Mario Waser

Beilstein J. Org. Chem. 2021, 17, 800–804, doi:10.3762/bjoc.17.68

• rac-2 with anhydride 4aa. Supporting Information Supporting Information File 70: Copies of NMR spectra and HPLC chromatograms as well as analytical data of esters 3 obtained with the alternative acyl-transfer reagents 4. Acknowledgements We are grateful to Thomas Bögl (Institute of Analytical

• Chemistry, JKU Linz) for support with HRMS analysis. Funding This work was generously supported by the Austrian Science Funds (FWF): Project No. P31784. The used NMR spectrometers were acquired in collaboration with the University of South Bohemia (CZ) with financial support from the European Union through

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• -403 Łódź, Poland Department of Inorganic and Analytical Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Łódź, Poland Institute of Physics, University of Silesia, 75 Pułku Piechoty 1, 41-500 Chorzów, Poland Department of Physical Chemistry, Theoretical and Structural Chemistry

Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones

• Viktor M. Tkachuk,
• Oleh O. Lukianov,
• Mykhailo V. Vovk,
• Isabelle Gillaizeau and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191

• Viktor M. Tkachuk Oleh O. Lukianov Mykhailo V. Vovk Isabelle Gillaizeau Volodymyr A. Sukach Institute of Organic Chemistry, National Academy of Sciences of Ukraine Institute of Organic and Analytical Chemistry, ICOA UMR 7311 CNRS, Université d’Orléans, rue de Chartres, 45100 Orléans, France

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

• : Here, we briefly summarize the importance of fluorine atoms in organic molecules in the context of medicinal chemistry, materials chemistry, analytical chemistry and in the mechanistic studies of synthetic reactions. The importance of fluorination reactions in organic synthesis is reviewed exhaustively

• , decreases the environmental impact, and has new modes of action. In analytical chemistry, fluorine nuclei (19F) are ideal for quantitative integration in NMR spectroscopy, comparable to 1H NMR spectroscopy [25][26]. In contrast to 13C signals, fluorine signals are well-resolved, and the nuclear spin of

Design, synthesis and application of carbazole macrocycles in anion sensors

• Alo Rüütel,
• Ville Yrjänä,
• Sandip A. Kadam,
• Indrek Saar,
• Mihkel Ilisson,
• Astrid Darnell,
• Kristjan Haav,
• Tõiv Haljasorg,
• Lauri Toom,
• Johan Bobacka and
• Ivo Leito

Beilstein J. Org. Chem. 2020, 16, 1901–1914, doi:10.3762/bjoc.16.157

• instrumentation at the Estonian Center of Analytical Chemistry (http://www.akki.ee). Funding This work was supported by the Estonian Research Council grant PRG690, by the EU through the European Regional Development Fund (TK141 “Advanced materials and high-technology devices for energy recuperation systems”) and

Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

• Dominik Göbel,
• Marius Friedrich,
• Enno Lork and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2020, 16, 1683–1692, doi:10.3762/bjoc.16.139

• Dominik Gobel Marius Friedrich Enno Lork Boris J. Nachtsheim Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Straße 7, 28359 Bremen, Germany Department of Organic Chemistry, Technical University Kaiserslautern, Erwin-Schrödinger-Straße Geb.54, 67663 Kaiserslautern

Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

• Csilla Hargitai,
• Györgyi Koványi-Lax,
• Tamás Nagy,
• Péter Ábrányi-Balogh,
• András Dancsó,
• Gábor Tóth,
• Judit Halász,
• Angéla Pandur,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2020, 16, 1636–1648, doi:10.3762/bjoc.16.136

• Centre for Natural Sciences, P.O. Box 286, H-1519 Budapest, Hungary Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary 10.3762/bjoc.16.136 Abstract Treatment of alkoxy-substituted o-(pivaloylaminomethyl

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

• Grzegorz Mlostoń,
• Mateusz Kowalczyk,
• André U. Augustin,
• Peter G. Jones and
• Daniel B. Werz

Beilstein J. Org. Chem. 2020, 16, 1288–1295, doi:10.3762/bjoc.16.109

• of Sciences Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany, Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany 10.3762/bjoc.16.109 Abstract Ferrocenyl

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

• Péter Bagi,
• Réka Herbay,
• Nikolett Péczka,
• Zoltán Mucsi,
• István Timári and
• György Keglevich

Beilstein J. Org. Chem. 2020, 16, 818–832, doi:10.3762/bjoc.16.75

• Analytical Chemistry, University of Debrecen, H-4032 Debrecen, Hungary 10.3762/bjoc.16.75 Abstract A series of 1-substituted-3-methyl-2-phospholene oxides was prepared from the corresponding 3-phospholene oxides by double bond rearrangement. The 2-phospholene oxides could be obtained by heating the 3