European Journal of Organic Chemistry

Cover image for Vol. 2017 Issue 8

Editor: Haymo Ross, Deputy Editor: Anne Nijs

Impact Factor: 3.068

ISI Journal Citation Reports © Ranking: 2015: 17/59 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

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February 21, 2017

VIP: Suzuki–Miyaura Coupling of Verdazyl Radicals

Thanh-Ngoc Le, Theresa Trevisan, Elizabeth Lieu and David J. R. Brook

Suzuki–Miyaura Coupling of Verdazyl Radicals

Halogenated aryl verdazyl radicals can be coupled with boronic acids under standard Suzuki–Miyaura conditions. The same reaction conditions can be used to generate boronate ester substituted verdazyl radicals that can undergo further coupling with aryl iodides. These reactions reveal new pathways to synthesize radical-substituted materials and, particularly, conjugated systems.

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February 04, 2017

VIP: Synthesis of N-Heteroaromatic Compounds through Cyclocarbonylative Sonogashira Reactions

Laura Antonella Aronica, Gianluigi Albano, Luca Giannotti and Elisa Meucci

Synthesis of N-Heteroaromatic Compounds through Cyclocarbonylative Sonogashira Reactions

A one-step synthesis of functionalised isoindolines and dihydrobenzoazepines was developed through copper-free, palladium-catalysed cyclocarbonylative Sonogashira reactions between tosylamides and iodoarenes.

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January 25, 2017

VIP: Mechanochemical Synthesis of Dipeptides Using Mg-Al Hydrotalcite as Activating Agent under Solvent-Free Reaction Conditions

José M. Landeros and Eusebio Juaristi

Mechanochemical Synthesis of Dipeptides Using Mg-Al Hydrotalcite as Activating Agent under Solvent-Free Reaction Conditions

An efficient protocol for the synthesis of several α,α-, α,β-, and β,β-dipeptides under ball-milling activation and solvent-free conditions has been developed. The reaction takes place in the presence of coupling agents EDC, HOBt, and with Mg-Al hydrotalcite as activator.

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January 24, 2017

VIP: Aromatic Esters, Carbinols, and Derivatives Thereof with Perfluorohexyl Residues as Alternatives to Perfluoroalkanecarboxylic and -sulfonic Acids

Torben Alpers, Thomas W. T. Muesmann, Oliver Temme and Jens Christoffers

Aromatic Esters, Carbinols, and Derivatives Thereof with Perfluorohexyl Residues as Alternatives to Perfluoroalkanecarboxylic and -sulfonic Acids

Short, but still repellent. Aromatic esters and carbinols with perfluorohexyl residues and some derivatives thereof have been prepared as novel, biodegradable materials for textile impregnation.

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December 15, 2016

VIP: In Vitro Photodynamic Studies of a BODIPY-Based Photosensitizer

Bosung Kim, Binglin Sui, Xiling Yue, Simon Tang, Michael G. Tichy and Kevin D. Belfield

In Vitro Photodynamic Studies of a BODIPY-Based Photosensitizer

Facile synthesis of an iodinated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivative exhibited highly efficient singlet-oxygen sensitization. Photodynamic-therapy activity experiments showed photo-induced necrotic cell death in Lewis lung carcinoma cells.

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December 14, 2016

VIP: One-Pot Preparation of Non-Symmetric meso-Aryl-BODIPYs: Functional Derivatives with Unusual Reactivity

Clemens Cidarér, Martin Hoffmann, Julian Oelmann, Benedikt Wolfram and Martin Bröring

One-Pot Preparation of Non-Symmetric meso-Aryl-BODIPYs: Functional Derivatives with Unusual Reactivity

Five molecules meet in a one-pot assembly to form non-symmetric meso-aryl-BODIPY luminophores in a quick and efficient single procedure and without the need of an oxidant. The new derivatives display the expected reactivity at the free α position, but also show selective chlorination at unexpected sites.

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December 13, 2016

VIP: Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence

Julian Diehl and Reinhard Brückner

Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence

A route to β-keto Weinreb amides was developed. These compounds were hydrogenated in the presence of [Me2NH2]+{[RuCl(S)-BINAP]2(µ-Cl)3} (0.5 mol-%) at 5 bar pressure (up to 99 % ee). The resulting β-hydroxy Weinreb amides reacted with organolithium or Grignard reagents to give enantiopure β-hydroxy ketones. These gave syn-1,3-diols by Narasaka–Prasad reduction or anti-1,3-diols by hydrogenation.

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December 12, 2016

VIP: Facile Synthesis of Polysubstituted Imidazoles through CBr4-Mediated Tandem Cyclization of Amidines with 1,3-Dicarbonyl Compounds or Ketones

Xiaoqiang Zhou, Haojie Ma, Chong Shi, Yixin Zhang, XingXing Liu and Guosheng Huang

Facile Synthesis of Polysubstituted Imidazoles through CBr4-Mediated Tandem Cyclization of Amidines with 1,3-Dicarbonyl Compounds or Ketones

A facile metal-free approach to synthesize polysubstituted imidazoles through a CBr4-mediated tandem cyclization of amidines with 1,3-dicarbonyl compounds or ketones is described to afford the desired products in moderate to good yields by using simple operation techniques and mild conditions.

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December 07, 2016

VIP: 3-Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of ortho-Functionalized Cinnamic Esters

Slim Chaabouni, Florent Simonet, Alison François, Souhir Abid, Chantal Galaup and Stefan Chassaing

3-Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of ortho-Functionalized Cinnamic Esters

A method for the regioselective synthesis of 3-trifluoromethylated coumarins and carbostyrils by the direct trifluoromethylation of appropriately substituted ortho-functionalized esters is described. The reaction proceeds by using the Togni reagent as the CF3 source under mild conditions and shows good functional-group tolerance.

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December 05, 2016

VIP: Synthesis and Biological Evaluation of Migrastatin Macrotriazoles

Adele Gabba, Stefania Robakiewicz, Bartłomiej Taciak, Katarzyna Ulewicz, Gianluigi Broggini, Giulio Rastelli, Magadalena Krol, Paul V. Murphy and Daniele Passarella

Synthesis and Biological Evaluation of Migrastatin Macrotriazoles

Three macrotriazole analogues of the natural product migrastatin were synthesized by using copper(I)- or ruthenium-catalyzed azide–alkyne cycloaddition reactions. The intermediary enantiopure terminal alkynes were synthesized through Trost desymmetrization, Brown alkoxyallylation and efficient Colvin reaction. The compounds were found to reduce the ability of MDA-MB-361 cell lines to migrate.

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December 05, 2016

VIP: β-Amyrin Biosynthesis: Effect of Steric Bulk at the 6-, 10- and 15-Positions in the 2,3-Oxidosqualene Backbone on Polycyclisation Cascades

Yuri Terasawa, Yusuke Sasaki, Yuki Yamaguchi, Kazunari Takahashi and Tsutomu Hoshino

β-Amyrin Biosynthesis: Effect of Steric Bulk at the 6-, 10- and 15-Positions in the 2,3-Oxidosqualene Backbone on Polycyclisation Cascades

On the methyl binding sites in the reaction cavity of β-amyrin synthase: the catalytic domain responsible for the earlier stages of the polycyclisation reaction is notably compact, whereas the domain for the later stages is relatively loosely packed.

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November 30, 2016

VIP: Substrate-Selective Olefin Hydrogenation with a Cavitand-Based Bis(N-anisyl iminophosphorane)

Thierry Chavagnan, Claude Bauder, David Sémeril, Dominique Matt and Loïc Toupet

Substrate-Selective Olefin Hydrogenation with a Cavitand-Based Bis(N-anisyl iminophosphorane)

A resorcin[4]arene cavitand with two N-anisyl iminophosphoranyl (AIP) units has been synthesized and applied in the rhodium-catalysed competitive hydrogenation of α-olefins. The system was shown to be suitable for the preferential conversion of hex-1-ene vs. that of 3-ethylpent-1-ene, as well as the regioselective reduction of a compound with two double bonds in different steric environments.

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February 21, 2017
VIP: Suzuki–Miyaura Coupling of Verdazyl Radicals

February 04, 2017
VIP: Synthesis of N-Heteroaromatic Compounds through Cyclocarbonylative Sonogashira Reactions

January 25, 2017
VIP: Mechanochemical Synthesis of Dipeptides Using Mg-Al Hydrotalcite as Activating Agent under Solvent-Free Reaction Conditions

January 24, 2017
VIP: Aromatic Esters, Carbinols, and Derivatives Thereof with Perfluorohexyl Residues as Alternatives to Perfluoroalkanecarboxylic and -sulfonic Acids

December 15, 2016
VIP: In Vitro Photodynamic Studies of a BODIPY-Based Photosensitizer

December 14, 2016
VIP: One-Pot Preparation of Non-Symmetric meso-Aryl-BODIPYs: Functional Derivatives with Unusual Reactivity

December 13, 2016
VIP: Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence

December 12, 2016
VIP: Facile Synthesis of Polysubstituted Imidazoles through CBr4-Mediated Tandem Cyclization of Amidines with 1,3-Dicarbonyl Compounds or Ketones

December 07, 2016
VIP: 3-Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of ortho-Functionalized Cinnamic Esters

December 05, 2016
VIP: Synthesis and Biological Evaluation of Migrastatin Macrotriazoles

December 05, 2016
VIP: β-Amyrin Biosynthesis: Effect of Steric Bulk at the 6-, 10- and 15-Positions in the 2,3-Oxidosqualene Backbone on Polycyclisation Cascades

November 30, 2016
VIP: Substrate-Selective Olefin Hydrogenation with a Cavitand-Based Bis(N-anisyl iminophosphorane)

November 22, 2016
VIP: Catalytic Asymmetric Synthesis of Chiral Dihydrobenzofurans through a Formal [4+1] Annulation Reaction of Sulfur Ylides and In Situ Generated ortho-Quinone Methides

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