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A Substituent‐Directed Strategy for the Selective Synthesis of L‐Hexoses: An Expeditious Route to L‐Idose Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-02 Nicholas W. See; Norbert Wimmer; Elizabeth H. Krenske; Vito Ferro
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Late‐stage Rh(II)‐catalyzed Nitrene Transfer for the Synthesis of Guaianolide Analogs with Enhanced Antiproliferative Activity Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-12 Sebastián J. Castro; José M. Padrón; Benjamin Darses; Viviana E. Nicotra; Philippe Dauban
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Perfluorophenyl‐Perfluorophenyl Stacking‐Promoted Aggregation‐Induced Emission Enhancement of Crystalline 5‐Aryloxy‐3H‐indole Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-25 Kazumasa Funabiki; Kengo Yamada; Hisaki Matsueda; Yuta Arisawa; Tomohiro Agou; Yasuhiro Kubota; Toshiyasu Inuzuka; Hiroaki Wasada
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Continuous flow synthesis of azoxybenzenes by reductive dimerization of nitrosobenzenes with gel‐bound catalysts Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-24 Carsten J. Schmiegel; Patrik Berg; Franziska Obst; Roland Schoch; Dietmar Appelhans; Dirk Kuckling
In search for a new synthetic pathway for azoxybenzenes with different substitution patterns, an approach using a microfluidic reactor with gel‐bound proline organocatalysts under continuous flow is presented. Herein the formation of differently substituted azoxybezenes by reductive dimerization of nitrosobenzenes within minutes at mild conditions in good to almost quantitative yields is described
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Magnesium Monoperphthalate (MMPP): a Convenient Oxidant for the Direct Rubottom Oxidation of Malonates, β‐Keto Esters and Amides Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-24 Alessandra Lattanzi; Sara Meninno; Rosaria Villano
A mild and convenient protocol for the a‐hydroxylation of a‐substituted malonates, b‐ketoesters and b‐ketoamides is disclosed. Cheap and stable magnesium monoperphthalate (MMPP) was effective for a first direct a‐hydroxylation protocol of the Rubottom oxidation, providing tartronic esters, cyclic a‐hydroxy b‐ketoesters and amides in good to high yields, when working at room temperature and in ethanol
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Synthesis of Polyciclic Chromene Cores through Gold (I)‐Catalyzed Intramolecular Hydroarylation Reaction (IMHA) Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-24 Antonia Iazzetti; Antonio Arcadi; Giancarlo Fabrizi; Andrea Fochetti; Roberta Franzini; Francesca Ghirga; Antonella Goggiamani; Federico Marrone; Andrea Serraiocco
A regioselective gold (I)‐catalyzed approach for the construction of polycyclic chromene cores has been developed. The reaction proceeds in good to excellent yields under mild condition with a broad range of substrates providing a simple and efficient tool for the synthesis of pyranochromene derivatives. Moreover, the regiochemical control of the annulation of unsymmetrically substituted propargylic
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Copper‐Catalyzed Cross‐Dehydrogenative Coupling Reactions Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-24 C. M. A. Afsina; Thaipparambil Aneeja; Mohan Neetha; Gopinathan Anilkumar
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Pd‐Catalyzed Cascade Metallo‐Ene Cyclization/Metallo‐Carbene Coupling of Allenamides Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-09 Chengqiang Cao; Yi Yang; Xin Li; Yunxia Liu; Hui Liu; Zengdian Zhao; Lei Chen
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Front Cover: Highly Enantioselective Ring‐Opening of meso‐Epoxides with O‐ and N‐Nucleophiles Catalyzed by a Chiral Sc(III)/bipyridine Complex (Eur. J. Org. Chem. 8/2021) Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-16 Štefan Malatinec; Eva Bednářová; Hiroki Tanaka; Martin Kotora
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Cover Feature: Use of Perylene Diimides in Synthetic Photochemistry (Eur. J. Org. Chem. 8/2021) Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-16 Cristian Rosso; Giacomo Filippini; Maurizio Prato
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Use of Perylene Diimides in Synthetic Photochemistry Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-05 Cristian Rosso; Giacomo Filippini; Maurizio Prato
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Recent Advances in the Synthesis of Sulfonylureas Eur. J. Org. Chem. (IF 2.889) Pub Date : 2020-12-21 Tiziano De Ventura; Vinicio Zanirato
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Recent Developments in Deaminative Functionalization of Alkyl Amines Eur. J. Org. Chem. (IF 2.889) Pub Date : 2020-12-21 Yi‐Na Li; Fang Xiao; Yu Guo; Yao‐Fu Zeng
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Updating the CSIC Reaction (2003–2020) Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-22 Alexey V. Dobrydnev; José Marco‐Contelles
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Highly Enantioselective Ring‐Opening of meso‐Epoxides with O‐ and N‐Nucleophiles Catalyzed by a Chiral Sc(III)/bipyridine Complex Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-16 Štefan Malatinec; Eva Bednářová; Hiroki Tanaka; Martin Kotora
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Biomimetic Syntheses of Amorfrutin C and C‐5 Substituted Amorfrutin Analogues Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-27 Calum Patel; Thomas Mies; Andrew J. P. White; Philip J. Parsons; Anthony G. M. Barrett
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Synthesis of (±)‐epi‐Jungianol by the Gold(I)‐Catalyzed Propargyl Claisen Rearrangement/Hydroarylation Cascade Reaction of Propargyl Vinyl Ethers Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-21 Antonia Rinaldi; Vittoria Langé; Dina Scarpi; Ernesto G. Occhiato
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Oxidative Rearrangement of 2‐(2‐Aminobenzyl)furans: Synthesis of Functionalized Indoles and Carbazoles Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-09 Anton A. Merkushev; Anton S. Makarov; Pavel M. Shpuntov; Vladimir T. Abaev; Igor V. Trushkov; Maxim G. Uchuskin
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A Novel and Practical Continuous Flow Chemical Synthesis of Cannabidiol (CBD) and its CBDV and CBDB Analogues Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-15 Elena Chiurchiù; Susanna Sampaolesi; Pietro Allegrini; Daniele Ciceri; Roberto Ballini; Alessandro Palmieri
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Rhodium(III)‐Catalyzed Oxidative Annulation of Amidines with Alkynes via Sequential C−H Bond Activation Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-07 Yan‐Yu Meng; Wen‐Jing Zhu; Yuan‐Yuan Song; Gang‐Gang Bu; Li‐Juan Zhang; Fen Xu
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Synthesis and Molecular Properties of Partially Fluorinated DNTTs** Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-11 Matthias W. Tripp; Daniel Bischof; Maximilian Dreher; Gregor Witte; Ulrich Koert
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4‐Aryl‐2‐Imino‐1,3‐Dithiolanes from the Room Temperature Coupling of Sodium Dithiocarbamates with Sulfonium Salts Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-23 Giulio Bresciani; Fabio Marchetti; Gianluca Ciancaleoni; Guido Pampaloni
A series of 4‐aryl‐2‐imino‐1,3‐dithiolanes was synthesized by means of a straightforward strategy starting from readily available precursors: reactions of dithiocarbamates and arylsulfonium salts, at room temperature in water/CH 2 Cl 2 as biphasic medium, afforded the five‐membered cyclic products in good yields. The reaction mechanism was investigated by DFT calculations.
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Oxoammonium‐mediated allylsilane‐ether coupling reaction Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-23 Federica Carlet; Greta Bertarini; Gianluigi Broggini; Alexandre Pradal; Giovanni Poli
A new C(sp 3 )‐H functionalization reaction consisting in the oxidative α‐allylation of allyl‐ and benzyl‐ methyl ethers has been developed. The C‐C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.
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Spiro‐2‐oxindoles via 1,3‐dipolar cycloadditions. A decade update. Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-23 Giorgio Molteni; Alessandra Silvani
The huge variety of spirooxindole three‐dimensional scaffolds encompasses relevant bioactive natural alkaloids as well as useful therapeutic agents. In view of the challenging features of the spirooxindole skeletons and their desirable properties, several synthetic routes have been devoted to their preparation. Because of the variety of both 1,3‐dipolar species and 2‐oxindoles bearing a C=X double
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Atroposelective Synthesis of Isoriccardin C through a C−H Activated Heck Type Macrocyclization Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-23 Lisa Marx; Daniel Lamberty; Sabine Choppin; Françoise Colobert; Andreas Speicher
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Synthesis of γ‐Spirolactams by Birch Reduction of Arenes Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-21 Tobias Krüger; Torsten Linker
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Arsenic‐Bridged Silafluorene and Germafluorene as a Novel Class of Mixed‐Heteroatom‐Bridged Heterofluorenes Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-27 Hiroshi Sasaki; Ippei Akioka; Hiroaki Imoto; Kensuke Naka
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Iridium Complexes as Efficient Catalysts for Construction of α‐Substituted Ketones via Hydrogen Borrowing of Alcohols in Water Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-05 Nianhua Luo; Yuhong Zhong; Huiling Wen; Hongling Shui; Renshi Luo
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Transition‐Metal‐Free Matsuda‐Heck Type Cross‐Coupling and Mechanistic Evidence for a Radical Mechanism Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-22 Julien Bergès; Yassir Zaid; Anis Tlili; Jean‐Marc Sotiropoulos; Marc Taillefer
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Sulfonium Salts Enable the Direct Sulfenylation of Activated C(sp3)−H Bonds Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-20 Liang Zhang; Sakkani Nagaraju; Banoth Paplal; Yunliang Lin; Shuhua Liu
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Synthesis, Radiosynthesis, and in vitro Studies on Novel Hypoxia PET Tracers Incorporating [18F]FDR Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-09 Manuele Musolino; Ian N. Fleming; Lutz F. Schweiger; David O'Hagan; Sergio Dall'Angelo; Matteo Zanda
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Synthesis and Liquid Crystalline Self‐Assembly of Concave Diindoles with a Hydropentalene Core Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-29 Andrea Bühlmeyer; Philipp Ehni; Dustin Ullmann; Wolfgang Frey; Angelika Baro; Sabine Laschat
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The winding road towards an atropo‐enantioselective ‘ARYNE coupling’ Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-19 David Augros; Corinne Comoy; Yves Fort; Frédéric R. Leroux; Armen Panossian
For the first time, the challenging atropo‐enantioselective coupling of in‐situ generated arynes and aryllithiums in the presence of a chiral ligand of lithium was investigated. This preliminary study demonstrates the feasibility of this concept, by affording enantioenriched axially chiral biaryls even in the case of products showing a high degree of steric congestion around the newly created aryl‐aryl
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A Concise Stereoselective Total Synthesis of Methoxyl Citreochlorols & Their Structural Revisions. Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-19 Ranganayakulu Sunnapu; Rajendar Goreti
A concise stereoselective and protecting group free approaches for the total synthesis of (‐)‐(2 S ,4 R )‐ & (+)‐(2 R ,4 S )‐3'‐methoxyl citreochlorols and their stereoisomers are demonstrated. All four stereoisomers were synthesized to establish the absolute stereochemistry of the reported structures and the structures were revised accordingly. The approach involves chelation controlled regioselective
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Planar and rigid pyrazine based TADF emitter for deep blue bright organic light emitting diodes Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-19 Pachaiyappan Rajamalli; Dongyang Chen; Subeesh Madayanad Suresh; Youichi Tsuchiya; Chihaya Adachi; Eli Zysman-Colman
Two blue thermally activated delayed fluorescence (TADF) emitters bearing di‐ tert ‐butyl carbazoles as the electron donor groups and pyrazine ( DTCz‐Pz ) or dipyrazine ( DTCz‐Pz ) as the electron acceptor are presented. The DFT calculations predict DTCz‐Pz and DTCz‐DPz to possess high S 1 energies (3.19 eV and 3.08 eV, respectively), and relatively large ΔE ST values (0.52 eV and 0.56 eV, respectively)
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Intramolecular Heck Reaction in Total Synthesis of Natural Products: An Update Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-18 Rajib Kumar Goswami; Debobrata Paul; Subhendu Das; Sanu Saha; Himangshu Sharma
This review highlights the application of intramolecular Heck reaction in total synthesis of natural products which were synthesized successfully recently (2013 to 2019). Heck cyclization was used as one of the strategic steps for constructions of wide variety of cyclic scaffolds essential for preparation of the different natural products.
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The Asymmetric Difluoro‐Reformatsky Reaction Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-29 Manfred Braun
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Triptycene Boronates, Boranes, and Boron Ate‐Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-03 Mathieu Gama; Xavier Antognini Silva; Thu‐Hong Doan; Arnaud Osi; Aurélien Chardon; Nikolay Tumanov; Johan Wouters; Guillaume Berionni
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Nickel‐Catalyzed Regioselective Arylboration of Conjugated Dienes Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-05 Haoyang Li; Jiao Long; Yuqiang Li; Wang Wang; Hailiang Pang; Guoyin Yin
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Organocatalytic Amination of Pyrazolones with Azodicarboxylates: Scope and Limitations. Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-16 Bedřich Formánek; Vít Šeferna; Marta Meazza; Ramon Rios; Mahendra Patil; Jan Vesely
The organocatalytic amination of pyrazol‐5‐ones with azodicarboxylates (catalyzed by quinine) is reported. This asymmetric process furnishes enantiomerically enriched hydrazine adducts containing quaternary stereocenters in high yields (74‐96%) and enantioselectivities (up to ee 97%). Theoretical calculations allow us to propose the relations between quinine catalyst and reactants leading to observed
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Ruthenium(II)‐Catalyzed C−H Activation/Annulation of Aromatic Hydroxamic Acid Esters with Enamides Leading to Aminal Motifs Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-29 Suman Dana; Popuri Sureshbabu; Chandan Kumar Giri; Mahiuddin Baidya
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Highly Efficient DMSO‐Promoted α‐Hydrolysis of α‐Halohydroxamates under Mild Conditions Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-02 Chang Yoon Lee; Sung‐Gon Kim
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Catalytic Asymmetric Carbene Insertion Reactions into B−H Bonds Using a Ru(II)‐Pheox Complex Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-15 Nansalmaa Otog; Soda Chanthamath; Ikuhide Fujisawa; Seiji Iwasa
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Methylthiolation for Electron‐Rich Heteroarenes with DMSO‐TsCl Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-04 Lei‐Yang Zhang; Yue‐Hua Wu; Nai‐Xing Wang; Xue‐Wang Gao; Zhan Yan; Bao‐Cai Xu; Ning Liu; Bo‐Zhou Wang; Yalan Xing
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Synthesis of Isatin‐Hydrazones from 3‐Diazo Oxindoles and Sulfoxonium Ylides under Catalyst‐ and Additive‐Free Conditions Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-27 Yu Tian; Zunting Zhang; Tao Wang
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Synthesis of Azepino[1,2‐a]indole‐10‐amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-03 Ryoya Iioka; Kohei Yorozu; Yoko Sakai; Rika Kawai; Noriyuki Hatae; Katsuki Takashima; Genzoh Tanabe; Hiroaki Wasada; Mitsuhiro Yoshimatsu
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Formal Semisynthesis of Demethylgorgosterol Utilizing a Stereoselective Intermolecular Cyclopropanation Reaction Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-23 Nicolai Rosenbaum; Lisa Schmidt; Florian Mohr; Olaf Fuhr; Martin Nieger; Stefan Bräse
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One‐Pot Synthesis of 5‐Amino‐1,2,3‐triazole Derivatives via Dipolar Azide−Nitrile Cycloaddition and Dimroth Rearrangement under Solvent‐Free Conditions Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-27 Pavel S. Gribanov; Edita M. Atoian; Anna N. Philippova; Maxim A. Topchiy; Andrey F. Asachenko; Sergey N. Osipov
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Strengths of Acids in Acetonitrile Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-27 Agnes Kütt; Sofja Tshepelevitsh; Jaan Saame; Märt Lõkov; Ivari Kaljurand; Sigrid Selberg; Ivo Leito
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Gallium(III) Corrole Complexes as Near‐Infrared Emitter – Synthesis, Computational and Photophysical Study Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-04 Michael Haas; Dominik Krisch; Sabrina Gonglach; Matthias Bechmann; Markus C. Scharber; Martin Ertl; Uwe Monkowius; Wolfgang Schöfberger
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Synthesis of Alkyl Bridged‐Tris‐α‐Amino Acids as C3‐Symmetric and Linear Linkers Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-25 Ayumi Uchino; Chihiro Tsukano; Tsuneo Imamoto; Kazuhiro Irie
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Front Cover: C(sp2)−Si Bond Functionalization through Intramolecular Activation by Alkoxides (Eur. J. Org. Chem. 7/2021) Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-09 Sebastien Curpanen; Giovanni Poli; Julie Oble.; Alejandro Perez‐Luna
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Cover Feature: An Insight into Non‐Covalent Interactions on the Bicyclo[1.1.1]pentane Scaffold (Eur. J. Org. Chem. 7/2021) Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-02-09 Nitika Grover; Keith J. Flanagan; Cristina Trujillo; Christopher J. Kingsbury; Mathias O. Senge
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Design, Synthesis, and Evaluation of α‐(Hydroxymethyl)cycloalkanols Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-07 Youssef Nassar; Olivier Piva
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C(sp2)−Si Bond Functionalization through Intramolecular Activation by Alkoxides Eur. J. Org. Chem. (IF 2.889) Pub Date : 2020-12-11 Sebastien Curpanen; Giovanni Poli; Julie Oble.; Alejandro Perez‐Luna
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Mechanistic Vistas of Trivalent Nitrogen Compound Reduction by Samarium Diiodide Eur. J. Org. Chem. (IF 2.889) Pub Date : 2020-12-09 Sandeepan Maity; Shmaryahu Hoz
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Synthesis, Self‐Assembly, and Nucleic Acid Recognition of an Acylhydrazone‐Conjugated Cationic Tetraphenylethene Ligand Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-15 Maëva Coste; Clément Kotras; Yannick Bessin; Virginie Gervais; David Dellemme; Maxime Leclercq; Mathieu Fossépré; Sébastien Richeter; Sébastien Clément; Mathieu Surin; Sébastien Ulrich
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Pd‐Catalyzed Regio‐ and Stereoselective sp3 C−H Arylation of Primary Aliphatic Amines: Mechanistic Studies and Synthetic Applications Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-19 Hyeonbin Ha; Ho Jeong Choi; Hahyoun Park; Yunyeong Gwon; Jiin Lee; Jaesung Kwak; Min Kim; Byunghyuck Jung
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Electrostatics Favor PNA : DNA Stability over Stereochemistry in Pyrrolidine‐Based Cationic Dual‐Backbone PNA Analogues Eur. J. Org. Chem. (IF 2.889) Pub Date : 2021-01-11 Ashwani Sharma; Shahaji H. More; Krishna N. Ganesh
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Synthesis of Enantiopure 6,11‐Methylene Lipoxin B4 Methyl Ester Eur. J. Org. Chem. (IF 2.889) Pub Date : 2020-12-11 Lukas Trippe; Analuisa Nava; Andrea Frank; Udo Nubbemeyer
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