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.

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

Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

• Liliia Moshniaha,
• Marika Żyła-Karwowska,
• Joanna Cybińska,
• Piotr J. Chmielewski,
• Ludovic Favereau and
• Marcin Stępień

Beilstein J. Org. Chem. 2020, 16, 895–903, doi:10.3762/bjoc.16.81

• Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, F-35000 Rennes, France 10.3762/bjoc.16.81 Abstract Boomerang-shaped bipyrroles containing donor–acceptor units were obtained through a tandem palladium-mediated reaction consisting of a cyclization step, involving double C–H bond

Diversity-oriented synthesis of 17-spirosteroids

• Benjamin Laroche,
• Thomas Bouvarel,
• Martin Louis-Sylvestre and
• Bastien Nay

Beilstein J. Org. Chem. 2020, 16, 880–887, doi:10.3762/bjoc.16.79

• Benjamin Laroche Thomas Bouvarel Martin Louis-Sylvestre Bastien Nay Unité Molécules de Communication et Adaptations des Micro-organismes (MCAM), Muséum National d'Histoire Naturelle, CNRS, Paris, France Laboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, ENSTA, Institut Polytechnique de

• spectra. Acknowledgements Dr. Alain Blond and Alexandre Deville are gratefully acknowledged for NMR spectra, and Dr. Sophie Bourcier for HRMS spectra. Funding We thank the CNRS "Fondation pour le développement de la Chimie des Substances Naturelles et ses Applications" for granting a PhD fellowship to BL

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

• Valerian Dragutan,
• Ileana Dragutan,
• Albert Demonceau and
• Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

• ] accomplished the convergent synthesis of des-epoxy-amphidinolide N (5) in 33 total steps (22 longest linear). To this end, after three generations of synthetic attempts, they succeeded joining the northern and southern fragments of des-epoxy-amphidinolide N, both endowed with a considerable level of structural

• -metal-catalyzed transformations were needed to achieve the total synthesis of des-epoxy-amphidinolide N, including a palladium asymmetric allylic alkylation (Pd-AAA), a Mukaiyama aldol reaction (with Sn), and a Krische allylation (with Ir) [72]. As special feature of this procedure, an Evans aldol

• reaction generated the syn aldol adduct, having the steric configuration imposed in des-epoxy-amphidinolide N. Also, in the last step of their work, Trost et al. managed to install the C14-OH via a finely tuned Rubottom oxidation that finalized the total synthesis of des-epoxy-amphidinolide N. Strikingly

Photoreversible stretching of a BAPTA chelator marshalling Ca²⁺-binding in aqueous media

• Aurélien Ducrot,
• Arnaud Tron,
• Robin Bofinger,
• Ingrid Sanz Beguer,
• Jean-Luc Pozzo and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2019, 15, 2801–2811, doi:10.3762/bjoc.15.273

• Aurelien Ducrot Arnaud Tron Robin Bofinger Ingrid Sanz Beguer Jean-Luc Pozzo Nathan D. McClenaghan Institut des Sciences Moléculaires, CNRS UMR 5255, Univ. Bordeaux, 351 cours de la Libération, 33405 Talence, France 10.3762/bjoc.15.273 Abstract Free calcium ion concentration is known to govern

A photochemical determination of luminescence efficiency of upconverting nanoparticles

• Baptiste Amouroux,
• Clément Roux,
• Jean-Claude Micheau,
• Fabienne Gauffre and
• Christophe Coudret

Beilstein J. Org. Chem. 2019, 15, 2671–2677, doi:10.3762/bjoc.15.260

• Baptiste Amouroux Clement Roux Jean-Claude Micheau Fabienne Gauffre Christophe Coudret Laboratoire des IMRCP, Université de Toulouse, CNRS UMR 5623, Université Toulouse III - Paul Sabatier,118 route de Narbonne, 31062 Toulouse, France Université de Rennes, CNRS, UMR6226, ISCR, F-35000 Rennes

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

• Zhen Cao,
• Aline Lacoudre,
• Cybille Rossy and
• Brigitte Bibal

Beilstein J. Org. Chem. 2019, 15, 2465–2472, doi:10.3762/bjoc.15.239

• Zhen Cao Aline Lacoudre Cybille Rossy Brigitte Bibal Université de Bordeaux, Institut des Sciences Moléculaires, UMR CNRS 5255, 351 cours de la libération, 33405 Talence, France 10.3762/bjoc.15.239 Abstract The bis-ortho-thioether 9,10-bis[(o-methylthio)phenyl]anthracene was synthesized as a syn

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

• Anne-Marie Caminade,
• Artem Zibarov,
• Eduardo Cueto Diaz,
• Aurélien Hameau,
• Maxime Klausen,
• Kathleen Moineau-Chane Ching,
• Jean-Pierre Majoral,
• Jean-Baptiste Verlhac,
• Olivier Mongin and
• Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

• Cedex 4, France LCC-CNRS, Université de Toulouse, CNRS, Toulouse, France Univ. Bordeaux, ISM (CNRS-UMR5255), Bat A12, 351 Cours de la Libération, 33400 Talence, France Univ. Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, F-35000 Rennes, France 10.3762/bjoc.15.221 Abstract

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

• Arnault Heynderickx,
• Sébastien Nénon,
• Olivier Siri,
• Vladimir Lokshin and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2019, 15, 2059–2068, doi:10.3762/bjoc.15.203

• Supporting Information File 110: Experimental and calculated IR spectra of 3, UV–vis absorption spectra of 3 in toluene and its fitting with Pekarian function, NMR spectra. Acknowledgements This work was supported by the Centre National de la Recherche Scientifique, the Ministère de la Recherche et des

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• Quentin Huaulme Cyril Aumaitre Outi Vilhelmiina Kontkanen David Beljonne Alexandra Sutter Gilles Ulrich Renaud Demadrille Nicolas Leclerc CEA, Univ. Grenoble Alpes, CNRS, IRIG, SyMMES, F-38000 Grenoble, France Chimie des Matériaux Nouveaux & Centre d'Innovation et de Recherche en Matériaux

Switchable selectivity in Pd-catalyzed [3 + 2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C–C/C–C vs C–C/O–C bond formation

• Yang Liu,
• Julie Oble and
• Giovanni Poli

Beilstein J. Org. Chem. 2019, 15, 1107–1115, doi:10.3762/bjoc.15.107

• Yang Liu Julie Oble Giovanni Poli Sorbonne Université, Faculté des Sciences et Ingénierie, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 4 place Jussieu, 75005 Paris, France 10.3762/bjoc.15.107 Abstract Two complementary [3 + 2] annulation protocols between 3-oxoglutarates and cyclic γ-oxy

Azologization of serotonin 5-HT₃ receptor antagonists

• Karin Rustler,
• Galyna Maleeva,
• Piotr Bregestovski and
• Burkhard König

Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74

• Karin Rustler Galyna Maleeva Piotr Bregestovski Burkhard Konig Institute of Organic Chemistry, University of Regensburg, 93053 Regensburg, Germany Aix-Marseille University, INSERM, INS, Institut de Neurosciences des Systèmes, 13005 Marseille, France Department of Normal Physiology, Kazan State

• hybrid biomolecule. In this context, various photochromic scaffolds including dithienylethenes, fulgi(mi)des, and azobenzenes are investigated [31][42]. The latter ones were already discovered in 1834 by E. Mitscherlich [43] but it took around another 100 years till G. S. Hartley [44] revealed their

Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes

• Guillaume Ernouf,
• Jean-Louis Brayer,
• Christophe Meyer and
• Janine Cossy

Beilstein J. Org. Chem. 2019, 15, 333–350, doi:10.3762/bjoc.15.29

• , 145 chemin des lilas, 59310 Beuvry-la-Forêt, France 10.3762/bjoc.15.29 Abstract Cyclopropenes constitute useful precursors of other classes of compounds incorporating a three-membered ring. Although the transformation of substituted cyclopropenes into alkylidenecyclopropanes can be accomplished

Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

• Pierre-Antoine Nocquet,
• Aurélie Macé,
• Frédéric Legros,
• Jacques Lebreton,
• Gilles Dujardin,
• Sylvain Collet,
• Arnaud Martel,
• Bertrand Carboni and
• François Carreaux

Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274

• Pierre-Antoine Nocquet Aurelie Mace Frederic Legros Jacques Lebreton Gilles Dujardin Sylvain Collet Arnaud Martel Bertrand Carboni Francois Carreaux Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, 263 avenue du Général Leclerc, Campus de Beaulieu, F-35000 Rennes

• , France Institut des Molécules et Matériaux du Mans, UMR 6283 CNRS-Université du Maine, avenue Olivier Messiaen, 72085 Cedex Le Mans, France Chimie Et Interdisciplinarité: Synthèse, Analyse, Modélisation (CEISAM), UMR 6230 CNRS-Université de Nantes, 2 chemin de la Houssinière, 44322 Cedex Nantes, France