Advancements in hydrochlorination of alkenes

• Daniel S. Müller

Beilstein J. Org. Chem. 2024, 20, 787–814, doi:10.3762/bjoc.20.72

• Daniel S. Muller Univ. Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) – UMR 6226, 263 Avenue du Général Leclerc, F-35000 Rennes, France 10.3762/bjoc.20.72 Abstract The hydrochlorination of alkenes has been extensively studied in research and is commonly featured in organic

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• adapted with permission of Institution of Chemical Engineers (IChemE) and The Royal Society of Chemistry from [38] (“Cationic and radical polymerization using a boron–thienothiophene–triphenylamine based D-π-A type photosensitizer under white LED irradiation”) by A. Suerkan et al., Mol. Syst. Des. Eng

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

• Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

• scaffolds is the introduction of a benzylidene moiety on C5 via a Knoevenagel reaction. Here, a facile synthesis of 5-arylidenerhodanines via a Knoevenagel reaction in an ʟ-proline-based deep eutectic solvent (DES) is reported. This method is fast (1 h at 60 °C), easy, catalyst-free and sustainable as no

• compounds are the more active ones. Keywords: antioxidant; deep eutectic solvent; Knoevenagel; ʟ-proline DES; rhodanine; Introduction Rhodanines and related five-membered heterocycles with multiple heteroatoms (i.e., thiazolidinediones, thiazolidinones, hydantoins, thiohydantoins) are very interesting

• , volatile solvents, hard conditions, and/or difficult purifications. However, green chemistry has become a crucial sub-discipline in the field of chemistry and the chemical industry is giving major priority to sustainable processes. Since a few years, deep eutectic solvents (DES) are considered as a

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

• Dileep Kumar Singh and
• Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

• bond donating groups were investigated. Among these, the DES prepared by mixing quaternary ammonium salts choline chloride (ChCl) and the hydrogen-bond donor L-(+)-tartaric acid gives the best result. Moreover, L-(+)-tartaric acid–ChCl acts as both solvent and catalyst for pyrrole synthesis. This

• interaction between DES and the amino group enhance the nucleophlicity of the amines. (3) Microwave-assisted reactions Microwave-assisted heating offers a number of advantages over conventional heating, such as greater precision, excellent product yields, and very rapid reaction. This section describes the

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K₃PO₄

• Ina Remy-Speckmann,
• Birte M. Zimmermann,
• Mahadeb Gorai,
• Martin Lerch and
• Johannes F. Teichert

Beilstein J. Org. Chem. 2023, 19, 440–447, doi:10.3762/bjoc.19.34

• Ina Remy-Speckmann Birte M. Zimmermann Mahadeb Gorai Martin Lerch Johannes F. Teichert Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 115, 10623 Berlin, Germany Fakultät für Naturwissenschaften, Technische Universität Chemnitz, Straße der Nationen 62, 09111 Chemnitz

Sequential hydrozirconation/Pd-catalyzed cross coupling of acyl chlorides towards conjugated (2E,4E)-dienones

• Benedikt Kolb,
• Daniela Silva dos Santos,
• Sanja Krause,
• Anna Zens and
• Sabine Laschat

Beilstein J. Org. Chem. 2023, 19, 176–185, doi:10.3762/bjoc.19.17

• ), the Ministerium für Wissenschaft, Forschung und Kunst des Landes Baden-Württemberg, the Fonds der Chemischen Industrie, the Merck KGaA, Darmstadt, is gratefully acknowledged.

Total synthesis of grayanane natural products

• Nicolas Fay,
• Rémi Blieck,
• Cyrille Kouklovsky and
• Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

• Nicolas Fay Remi Blieck Cyrille Kouklovsky Aurelien de la Torre Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), Université Paris-Saclay, CNRS, 15, rue Georges Clémenceau, 91405 Orsay Cedex, France 10.3762/bjoc.18.181 Abstract Grayananes are a broad family of diterpenoids found in

Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition

• Anaïs Rousseau,
• Guillaume Vincent and
• Cyrille Kouklovsky

Beilstein J. Org. Chem. 2022, 18, 1385–1395, doi:10.3762/bjoc.18.143

• Anais Rousseau Guillaume Vincent Cyrille Kouklovsky Institut de Chimie Moléculaire et des Matériaux d’Orsay, Université Paris-Saclay, CNRS, F-91405 Orsay, France 10.3762/bjoc.18.143 Abstract A convergent strategy for the synthesis of leustroducsins and phoslactomycins has been designed, relying

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• Yves L. Janin Structure et Instabilité des Génomes (StrInG), Muséum National d'Histoire Naturelle, INSERM, CNRS, Alliance Sorbonne Université, 75005 Paris, France 10.3762/bjoc.18.141 Abstract This perspective is an attempt to document the problems that medicinal chemists are facing in drug

On Reuben G. Jones synthesis of 2-hydroxypyrazines

• Pierre Legrand and
• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 935–943, doi:10.3762/bjoc.18.93

• Pierre Legrand Yves L. Janin Synchrotron SOLEIL, L'Orme des Merisiers, 91190 Saint-Aubin, France Structure et Instabilité des Génomes (StrInG), Muséum National d'Histoire Naturelle, INSERM, CNRS, Alliance Sorbonne Université, 75005 Paris, France 10.3762/bjoc.18.93 Abstract In 1949, Reuben G

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

• Girish Suresh Yedase,
• Sumit Kumar,
• Jessica Stahl,
• Burkhard König and
• Veera Reddy Yatham

Beilstein J. Org. Chem. 2021, 17, 1727–1732, doi:10.3762/bjoc.17.121

• Supporting Information File 152: Full experimental details, compound characterization, and copies of NMR spectra. Funding V.R.Y. acknowledges IISER-TVM for the financial support. GSY acknowledges the IISER TVM for the doctoral fellowship. JS thanks the Studienstiftung des Deutschen Volkes for a Ph.D stipend.

Correction: Amine–borane complex-initiated SF₅Cl radical addition on alkenes and alkynes

• Audrey Gilbert,
• Pauline Langowski,
• Marine Delgado,
• Laurent Chabaud,
• Mathieu Pucheault and
• Jean-François Paquin

Beilstein J. Org. Chem. 2021, 17, 1725–1726, doi:10.3762/bjoc.17.120

• Audrey Gilbert Pauline Langowski Marine Delgado Laurent Chabaud Mathieu Pucheault Jean-Francois Paquin Départment de chimie, Université Laval, Québec, QC, G1V 0A6, Canada Institut des Sciences Moléculaires - Groupe ORGA - UMR 5255, Université de Bordeaux, 351 Cours de la libération, 33405 Talence

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli,
• Noureddine Chaaben,
• Kamel Alimi,
• Stefan Jopp and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

• Monastir, Tunisia Universität Rostock, Institut für Chemie, Albert-Einstein-Str. 3a, 18059 Rostock, Germany Department of Chemistry, College of Science Al-zulfi, Majmaah University, Al-Majmaah, 11952, Saudi Arabia Université de Monastir, Faculté des Sciences, Unité de recherche sur les Hétéro-Epitaxies et

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

Nitroalkene reduction in deep eutectic solvents promoted by BH₃NH₃

• Chiara Faverio,
• Monica Fiorenza Boselli,
• Patricia Camarero Gonzalez,
• Alessandra Puglisi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2021, 17, 1041–1047, doi:10.3762/bjoc.17.83

• reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated. Keywords: alternative solvents; atom economy; DES; nitro derivatives; reduction; Introduction The search for alternative solvents, not

• physicochemical properties can be easily tuned and designed to meet specific requirements; they also offer the possibility to develop convenient methodologies to isolate the product by extraction or precipitation, and thus making the reuse of the DES mixture feasible. The large number of biodegradable raw

• report the results of our explorative studies, aimed to develop a chemoselective nitroalkene reduction in DESs, with the goals to establish a reliable and reproducible protocol to isolate the product without the use of any organic solvent and to assess the recovery and the recyclability of the DES

Synthesis of bis(aryloxy)fluoromethanes using a heterodihalocarbene strategy

• Carl Recsei and
• Yaniv Barda

Beilstein J. Org. Chem. 2021, 17, 813–818, doi:10.3762/bjoc.17.70

• 5 h, with 85% hydrolysis observed after 20 hours. The relative stability of 11 to acidic hydrolysis and its presumably enhanced lipophilicity with respect to a des-fluoro acetal, might presage a role for compounds possessing the acyclic bis(aryloxy)fluoromethane moiety in medicinal or agrochemical

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• filtration and reused. As an alternative to ILs, metal-based deep eutectic solvent (DES) systems were also explored as catalysts for the glycolysis reaction of PET using EG. DES have similar properties to metallated ILs, but they are cheaper and less toxic [232][233]. Because of this, they have found

• application in many fields [234][235], though they cannot be considered inherently “green” [236]. In a recent work, the DES combination zinc acetate and 1,3-dimethylurea (1:4) showed the highest catalytic activity among a series of transition metal acetates (Zn, Mn, Co, Ni, Cu), affording BHET with 82% yield

Amine–borane complex-initiated SF₅Cl radical addition on alkenes and alkynes

• Audrey Gilbert,
• Pauline Langowski,
• Marine Delgado,
• Laurent Chabaud,
• Mathieu Pucheault and
• Jean-François Paquin

Beilstein J. Org. Chem. 2020, 16, 3069–3077, doi:10.3762/bjoc.16.256

• Audrey Gilbert Pauline Langowski Marine Delgado Laurent Chabaud Mathieu Pucheault Jean-Francois Paquin Départment de chimie, Université Laval, Québec, QC, G1V 0A6, Canada Institut des Sciences Moléculaires - Groupe ORGA - UMR 5255, Université de Bordeaux, 351 Cours de la libération, 33405 Talence

3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia

• Florian Mann,
• Daiane Szczerbowski,
• Lisa de Silva,
• Melanie McClure,
• Marianne Elias and
• Stefan Schulz

Beilstein J. Org. Chem. 2020, 16, 2776–2787, doi:10.3762/bjoc.16.228

• , MNHN, Sorbonne Université, EPHE, Université des Antilles, 45 rue Buffon, CP 50, 75005 Paris, France Laboratoire Écologie, Évolution, Interactions des Systèmes Amazoniens (LEEISA), Université de Guyane, CNRS, IFREMER, 97300 Cayenne, France 10.3762/bjoc.16.228 Abstract Male ithomiine butterflies

Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups

• Benjamin Jeffries,
• Zhong Wang,
• Robert I. Troup,
• Anaïs Goupille,
• Jean-Yves Le Questel,
• Charlene Fallan,
• James S. Scott,
• Elisabetta Chiarparin,
• Jérôme Graton and
• Bruno Linclau

Beilstein J. Org. Chem. 2020, 16, 2141–2150, doi:10.3762/bjoc.16.182

• for a CASE Conversion grant (EP/M508147/1), a standard grant (EP/P019943/1), and a core capability grant (EP/K039466/1). The CCIPL (Centre de Calcul Intensif des Pays de Loire) is acknowledged for provision of computer time.

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

• Paola Vitale,
• Luciana Cicco,
• Ilaria Cellamare,
• Filippo M. Perna,
• Antonio Salomone and
• Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

• ][3]. As part of our ongoing research in DES chemistry, we reported recently on the preparation of valuable heterocycles by (a) nucleophilic substitution (tetrahydrofuran derivatives) [4], (b) heterocyclodehydration reactions (2-aminoimidazoles, 2-pyrazinones, benzoxazines, thiophenes) [5][6][7][8

• by dehydration. The two tautomers 3/3' would most probably originate by two competitive pathways (a and b; Scheme 4) via a [1,5]-hydrogen shift [28][29]. Hydrogen-bond catalysis promoted by DES components may be playing an important role in favoring the loss of nitrogen under mild conditions from a

• electron-donating groups like MeO. Studies to expand even more the scope and the selectivity of such DES-promoted heterocyclization reactions and to elucidate their mechanism are in progress. Experimental General methods Deep eutectic solvents [choline chloride (ChCl)/glycerol (Gly) (1:2 mol/mol); choline

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• Isaline Bonnin Raphael Mereau Thierry Tassaing Karine De Oliveira Vigier Université de Poitiers, IC2MP, UMR CNRS 7285, 1 rue Marcel Doré, 86073 Poitiers Cedex 9, France Institut des Sciences Moléculaires, UMR 5255 CNRS-Université de Bordeaux, 351 Cours de la Libération, 33405 Talence Cedex, France

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

• Natalie Lagesse Luca Pisciottani Maxime Douarre Pascale Godard Brice Kauffmann Vicente Marti-Centelles Nathan D. McClenaghan Institut des Sciences Moléculaires, CNRS UMR 5255, University of Bordeaux, Talence, France Institut Européen de Chimie et Biologie, CNRS UMS 3033, INSERM US001, University

• . Acknowledgements We thank the analytical facilities CESAMO (NMR and HRMS) of the Institut des Sciences Moléculaires, University of Bordeaux. Funding This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No. 796612