Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

• Layal Hariss,
• Kamal Bou Hadir,
• Mirvat El-Masri,
• Thierry Roisnel,
• René Grée and
• Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

• , Lebanon Université de Rennes 1, Institut des Sciences Chimiques de Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France 10.3762/bjoc.13.208 Abstract Using an aerobic oxidative coupling, different new imidazo[1,2-a]-N-heterocycles with gem-difluroroalkyl side chains have been

Peptide synthesis: ball-milling, in solution, or on solid support, what is the best strategy?

• Ophélie Maurin,
• Pascal Verdié,
• Gilles Subra,
• Frédéric Lamaty,
• Jean Martinez and
• Thomas-Xavier Métro

Beilstein J. Org. Chem. 2017, 13, 2087–2093, doi:10.3762/bjoc.13.206

• Ophelie Maurin Pascal Verdie Gilles Subra Frederic Lamaty Jean Martinez Thomas-Xavier Metro Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université de Montpellier, ENSCM, Campus Triolet, cc1703, Place Eugène Bataillon, 34095 Montpellier cedex 5, France 10.3762/bjoc.13.206

Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations

• Andrea Porcheddu,
• Evelina Colacino,
• Giancarlo Cravotto,
• Francesco Delogu and
• Lidia De Luca

Beilstein J. Org. Chem. 2017, 13, 2049–2055, doi:10.3762/bjoc.13.202

• Andrea Porcheddu Evelina Colacino Giancarlo Cravotto Francesco Delogu Lidia De Luca Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Cittadella Universitaria, SS 554 bivio per Sestu, 09028 Monserrato (Ca), Italy Institut des Biomolécules Max Mousseron (IBMM

Synthesis of benzannelated sultams by intramolecular Pd-catalyzed arylation of tertiary sulfonamides

• Valentin A. Rassadin,
• Mirko Scholz,
• Anastasiia A. Klochkova,
• Armin de Meijere and
• Victor V. Sokolov

Beilstein J. Org. Chem. 2017, 13, 1932–1939, doi:10.3762/bjoc.13.187

• and analytical data. Acknowledgements V.A.R. gratefully acknowledges the support of the Scientific Council of the President of the Russian Federation (Grant MK-2382.2017.3). M. S. is indebted to the Studienstiftung des Deutschen Volkes for a scholarship. All physicochemical measurements were

Influence of the milling parameters on the nucleophilic substitution reaction of activated β-cyclodextrins

• László Jicsinszky,
• Kata Tuza,
• Giancarlo Cravotto,
• Andrea Porcheddu,
• Francesco Delogu and
• Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 1893–1899, doi:10.3762/bjoc.13.184

• Montpellier, Institut des Biomolécules Max Mousseron (IBMM) UMR5247 CNRS-UM-ENSCM, Université de Montpellier, cc1703, Place Eugène Bataillon, 34095 Montpellier Cedex 05, France 10.3762/bjoc.13.184 Abstract The present work focuses on the mechanochemical preparation of industrially important β-cyclodextrin

Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation

• Raja Ben Othman,
• Mickaël J. Fer,
• Laurent Le Corre,
• Sandrine Calvet-Vitale and
• Christine Gravier-Pelletier

Beilstein J. Org. Chem. 2017, 13, 1533–1541, doi:10.3762/bjoc.13.153

• -Paris), 45 rue des Saints Pères, 75270 Paris 06, France 10.3762/bjoc.13.153 Abstract The 5’-alkynylation of uridine-derived aldehydes is described. The addition of alkynyl Grignard reagents on the carbonyl group is significantly influenced by the 2’,3’-di-O-protecting groups (R1): O-alkyl groups led to

How and why kinetics, thermodynamics, and chemistry induce the logic of biological evolution

• Addy Pross and
• Robert Pascal

Beilstein J. Org. Chem. 2017, 13, 665–674, doi:10.3762/bjoc.13.66

• Addy Pross Robert Pascal Department of Chemistry, Ben Gurion University of the Negev, Be’er Sheva 84105, Israel NYU Shanghai, 1555 Century Avenue, Pudong New Area, Shanghai, 200122, China, Institut des Biomolécules Max Mousseron, UMR5247 CNRS-University of Montpellier-ENSCM, CC17006, Place E

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

• Loïc Pantaine,
• Vincent Humblot,
• Vincent Coeffard and
• Anne Vallée

Beilstein J. Org. Chem. 2017, 13, 648–658, doi:10.3762/bjoc.13.64

• Loic Pantaine Vincent Humblot Vincent Coeffard Anne Vallee Institut Lavoisier de Versailles, UMR 8180, Université Paris-Saclay, Université de Versailles Saint-Quentin, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France Sorbonne Universités, UPMC Univ. Paris 06, Laboratoire de Réactivité de

• Surface, UMR CNRS 7197, 4 place Jussieu, 75005 Paris, France Université de Nantes, CNRS, CEISAM, UMR 6230, Faculté des Sciences et des Techniques, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France 10.3762/bjoc.13.64 Abstract Aniline-terminated self-assembled monolayers (SAMs) on gold surfaces

• sulfamide. Acknowledgements The authors acknowledge J. Vigneron for help with XPS data collection and the CEFS2 center for the use of XPS instrument. The authors would also like to thank IMPC (Institut des Matériaux de Paris Centre, FR2482) and the C’ Nano projects of the Region Ile-de-France for Omicron

Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

• Sophie Letort,
• Michaël Bosco,
• Benedetta Cornelio,
• Frédérique Brégier,
• Sébastien Daulon,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45

• Sophie Letort Michael Bosco Benedetta Cornelio Frederique Bregier Sebastien Daulon Geraldine Gouhier Francois Estour Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France DGA Maîtrise NRBC, Département Evaluation des effets des agents chimiques, 91710 Vert le Petit

Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues

• Bemba Sidi Mohamed,
• Christian Périgaud and
• Christophe Mathé

Beilstein J. Org. Chem. 2017, 13, 251–256, doi:10.3762/bjoc.13.28

• Bemba Sidi Mohamed Christian Perigaud Christophe Mathe Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, Université de Montpellier, CNRS, ENSCM, cc 1705, Site Triolet, Place Eugène Bataillon, 34095 Montpellier cedex 5, France 10.3762/bjoc.13.28 Abstract The racemic synthesis of new

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• component in the mixture [45]. Furthermore, it was reported that batch heating also resulted in the thermal degradation of choline chloride:D-fructose DES due to the caramelisation of D-fructose [45]. TSE overcame the problems identified by batch heating. The residence time for the continuous extrusion of

• the DES components was determined to be 4–8 minutes on average, producing quantities of ca. 0.4 kg h−1 (value of Reline 200 collected per hour) of DES [44]. The reaction times in the formation of DESs was greatly decreased, and as a result, thermal degradation was avoided in those DESs containing D

• material obtained, which may in turn make them a more accessible media for metal processing or an alternative green solvent for synthesis [44]. Metal-organic frameworks (MOFs) The above examples of cocrystal and DES formation describe systems which involve the formation of eutectic and intermolecular

Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins

• Andrea Mascitti,
• Massimiliano Lupacchini,
• Ruben Guerra,
• Ilya Taydakov,
• Lucia Tonucci,
• Nicola d’Alessandro,
• Frederic Lamaty,
• Jean Martinez and
• Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 19–25, doi:10.3762/bjoc.13.3

• Montpellier, Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS - UM - ENSCM, Place E. Bataillon, Campus Triolet, 34095 Montpellier CEDEX 5, France P.N. Lebedev Institute of Physics of RAS, Leninskiy pr-t, 53, 119991, Moscow, Russia Moscow Institute of Physics and Technology, Institutskiy per., 9

First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates

• Marwa Ayadi,
• Haitham Elleuch,
• Emmanuel Vrancken and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2906–2915, doi:10.3762/bjoc.12.290

• Marwa Ayadi Haitham Elleuch Emmanuel Vrancken Farhat Rezgui Université de Tunis El Manar, Faculté des Sciences de Tunis, Laboratoire de Chimie Organique Structurale LR99ES14, Campus Universitaire, 2092 Tunis, Tunisie Institut Charles Gerhardt UMR 5253 CNRS-UM-ENSCM, 8 rue de l'Ecole Normale 34296

cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

• Dimpee Gogoi,
• Runjun Devi,
• Pallab Pahari,
• Bipul Sarma and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2016, 12, 2816–2822, doi:10.3762/bjoc.12.280

• (containing a chroman unit) natural products (Figure 1) [2][3][4]. Their synthetic des-(angular)hydroxy derivatives (+)-brazilane (3) and haematoxylane (4) have also been mentioned in the literature [2][3][4]. Among them, brazilin (1), the most-studied member of this group, has been proved to have a number of

Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents

• Davide Brenna,
• Elisabetta Massolo,
• Alessandra Puglisi,
• Sergio Rossi,
• Giuseppe Celentano,
• Maurizio Benaglia and
• Vito Capriati

Beilstein J. Org. Chem. 2016, 12, 2620–2626, doi:10.3762/bjoc.12.258

• Mangiagalli 25, 20133 Milano, Italy Dipartimento di Farmacia–Scienze del Farmaco, Università di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, Italy 10.3762/bjoc.12.258 Abstract Different deep eutectic solvent (DES) mixtures were studied as reaction media for the continuous

• synthesis of enantiomerically enriched products by testing different experimental set-ups. L-Proline-catalysed cross-aldol reactions were efficiently performed in continuo, with high yield (99%), anti-stereoselectivity, and enantioselectivity (up to 97% ee). Moreover, using two different DES mixtures, the

• use of any organic solvent by a proper choice of DES components. The dramatic influence of the reaction media on the reaction rate and stereoselectivity of the process suggests that the intimate architecture of DESs deeply influences the reactivity of different species involved in the catalytic cycle

Inhibition of peptide aggregation by means of enzymatic phosphorylation

• Kristin Folmert,
• Malgorzata Broncel,
• Hans v. Berlepsch,
• Christopher H. Ullrich,
• Mary-Ann Siegert and
• Beate Koksch

Beilstein J. Org. Chem. 2016, 12, 2462–2470, doi:10.3762/bjoc.12.240

• , Umweltservice, Bahntechnikerring 74, 14774 Kirchmöser, Germany Department of Organic Chemistry, Technische Universität Berlin, Strasse des 17. Juni 124, 10623 Berlin, Germany 10.3762/bjoc.12.240 Abstract As is the case in numerous natural processes, enzymatic phosphorylation can be used in the laboratory to

Et₃B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols

• Ahlem Abidi,
• Yosra Oueslati and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2402–2409, doi:10.3762/bjoc.12.234

• Ahlem Abidi Yosra Oueslati Farhat Rezgui Université de Tunis EL Manar, Laboratoire de Chimie Organique Structurale et Macromoléculaire, Faculté des Sciences Campus Universitaire, 2092 Tunis, Tunisia 10.3762/bjoc.12.234 Abstract A practical and efficient palladium-catalyzed direct allylation of β

Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group

• Mariem Brahim,
• Hamed Ben Ammar,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2016, 12, 2197–2203, doi:10.3762/bjoc.12.210

• Mariem Brahim Hamed Ben Ammar Jean-Francois Soule Henri Doucet Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France. Tel.: 00-33-2-23-23-63-84 Laboratoire de Synthèse Organique Asymétrique

• et Catalyse Homogène, (UR 11ES56) Université de Monastir, Faculté des Sciences de Monastir, avenue de l’environnement, Monastir 5000, Tunisia 10.3762/bjoc.12.210 Abstract The use of a bromo-substituent as blocking group at the C2-position of 3-substituted thiophenes allows the regioselective

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• Elise Euvrard Nadia Morin-Crini Coline Druart Justine Bugnet Bernard Martel Cesare Cosentino Virginie Moutarlier Gregorio Crini Chrono-environnement, UMR 6249 usc INRA, University of Bourgogne Franche-Comté, 16 route de Gray, 25000 Besançon, France UMET UMR 8207, Ingénierie des Systèmes Polymères

Beta-hydroxyphosphonate ribonucleoside analogues derived from 4-substituted-1,2,3-triazoles as IMP/GMP mimics: synthesis and biological evaluation

• Tai Nguyen Van,
• Audrey Hospital,
• Corinne Lionne,
• Lars P. Jordheim,
• Charles Dumontet,
• Christian Périgaud,
• Laurent Chaloin and
• Suzanne Peyrottes

Beilstein J. Org. Chem. 2016, 12, 1476–1486, doi:10.3762/bjoc.12.144

• Tai Nguyen Van Audrey Hospital Corinne Lionne Lars P. Jordheim Charles Dumontet Christian Perigaud Laurent Chaloin Suzanne Peyrottes Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS – Université de Montpellier - ENSCM, Campus Triolet, cc1705, Place Eugène Bataillon, 34095 Montpellier

A convenient route to symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction

• Dariusz Błachut,
• Joanna Szawkało and
• Zbigniew Czarnocki

Beilstein J. Org. Chem. 2016, 12, 835–845, doi:10.3762/bjoc.12.82

• while suppressing the formation of the intermediate 3 and its des-brominated derivative 2 (Table 1). In a search for an efficient catalytic system, we took into consideration that dibromopyridine 1 having reaction sites at positions 3 and 5 of the pyridine ring, being shielded by methyl groups, might be

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• , Brazil Laboratoire de Pharmacognosie UMR/CNRS 8638 COMETE, Université Paris Descartes, Sorbonne Paris Cité, Faculté des Sciences Pharmaceutiques et Biologiques, 4 Avenue de l’observatoire 75006 Paris, France Laboratory of Molecular Parasitology, Department of Microbiology, Hellenic Pasteur Institute, 127

Recent advances in metathesis-derived polymers containing transition metals in the side chain

• Ileana Dragutan,
• Valerian Dragutan,
• Bogdan C. Simionescu,
• Albert Demonceau and
• Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

• of Eu-containing copolymers by a ROMP-based route. Acknowledgements The authors gratefully acknowledge support from the Romanian Academy and Ministry of Education and Research, as well as from Wallonie–Bruxelles International (WBI), the Direction générale des Relations extérieures de la Région

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• University College London, Gower Street, London WC1E 6BT, UK Laboratoire de Physicochimie des Polymères et des Interfaces (EA 2528), Institut des Matériaux, Université de Cergy-Pontoise, F-95031 Cergy-Pontoise Cedex, France 10.3762/bjoc.11.288 Abstract Two alternating polyfluorene polyrotaxanes (3·TM-βCD

Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp²)–H bond arylations

• Fatiha Abdelmalek,
• Fazia Derridj,
• Safia Djebbar,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2015, 11, 2012–2020, doi:10.3762/bjoc.11.218

• Fatiha Abdelmalek Fazia Derridj Safia Djebbar Jean-Francois Soule Henri Doucet Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 "Organométalliques, Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France Département de Chimie, UMMTO, University, BP 17 RP