European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 1

January 2015

Volume 2015, Issue 1

Pages 4–246

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreviews
    7. Short Communications
    8. Full Papers
    1. You have free access to this content
      Palladium-Catalyzed α-Arylation Reactions in Total Synthesis (Eur. J. Org. Chem. 1/2015)

      Sudheesh T. Sivanandan, Ashna Shaji, Ibrahim Ibnusaud, Carin C. C. Johansson Seechurn and Thomas J. Colacot

      Article first published online: 17 DEC 2014 | DOI: 10.1002/ejoc.201490106

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      The cover picture shows the scope of the α-arylation reaction of carbonyl compounds, such as ketones, aldehydes, esters and amides in the total syntheses of natural products and active pharmaceutical ingredients (API). This is exciting, because α-arylation reactions have emerged recently as one of the new trends in cross-coupling reactions, in which the CH at the α position of the carbonyl group undergoes functionalization by enolization in the presence of a base, followed by a C–C coupling under the influence of a metal catalyst, typically Pd. The potential of this powerful methodology will be enormous for key steps in organic synthesis for small and large molecules. Details are presented in the Microreview by T. J. Colacot et al. on 38 ff.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreviews
    7. Short Communications
    8. Full Papers
    1. You have free access to this content
      EurJOC Has Come a Long Way (pages 4–6)

      Haymo Ross

      Article first published online: 17 DEC 2014 | DOI: 10.1002/ejoc.201403496

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      Editor-in-chief Haymo Ross looks back at the important events for EurJOC in 2014, including the move to Editorial Manager, and gives a preview of what is to come in 2015.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreviews
    7. Short Communications
    8. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 1/2015 (pages 7–14)

      Article first published online: 17 DEC 2014 | DOI: 10.1002/ejoc.201490107

  4. News

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreviews
    7. Short Communications
    8. Full Papers
  5. Microreviews

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreviews
    7. Short Communications
    8. Full Papers
    1. Vicinal Quaternary Stereocenters

      The Nazarov Cyclization: A Valuable Method to Synthesize Fully Substituted Carbon Stereocenters (pages 23–37)

      Donald R. Wenz and Javier Read de Alaniz

      Article first published online: 9 SEP 2014 | DOI: 10.1002/ejoc.201402825

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      We describe three general approaches to the formation of fully substituted quaternary carbon stereocenters by means of the Nazarov cyclization.

    2. Pd in Natural Product Synthesis

      Palladium-Catalyzed α-Arylation Reactions in Total Synthesis (pages 38–49)

      Sudheesh T. Sivanandan, Ashna Shaji, Ibrahim Ibnusaud, Carin C. C. Johansson Seechurn and Thomas J. Colacot

      Article first published online: 19 NOV 2014 | DOI: 10.1002/ejoc.201403301

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      Metal-catalyzed α-arylation of carbonyl compounds has become a powerful tool for organic chemists to construct carbon-carbon bonds through C–H functionalization based on enolization. This microreview highlights recent applications of α-arylation in total syntheses both of natural products and of active pharmaceutical ingredients (APIs).

  6. Short Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreviews
    7. Short Communications
    8. Full Papers
    1. Multicomponent Reactions

      Concise Synthesis of Tetrazole–Ketopiperazines by Two Consecutive Ugi Reactions (pages 51–55)

      Tryfon Zarganes-Tzitzikas, Pravin Patil, Kareem Khoury, Eberhardt Herdtweck and Alexander Dömling

      Article first published online: 17 NOV 2014 | DOI: 10.1002/ejoc.201403401

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      A novel compound class of tetrazole–diketopiperazines is described. Two multicomponent reactions are used during the synthesis: the Ugi tetrazole four-component reaction (4CR) and the classical intramolecular Ugi 4CR. Tetrazole–diketopiperazines comprise analogs of and are bioisosteric to bioactive diketopiperazines. The scaffold is currently produced to fill the screening deck of the European Lead Factory.

    2. C–H Activation

      A Robust and Efficient Catalyst Possessing an Electron-Deficient Ligand for the Palladium-Catalyzed Direct Arylation of Heteroarenes (pages 56–59)

      Alexandra Jakab, Zoltán Dalicsek and Tibor Soós

      Article first published online: 31 OCT 2014 | DOI: 10.1002/ejoc.201402586

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      Application of a unique, thermally stable, and air-stable Pd0 catalyst for the direct arylation of heteroarenes is described. The combination of only 0.5–2 mol-% of the Pd0 complex possessing an electron-deficient fluorinated phosphine ligand with a substoichiometric quantity of pivalic acid (PivOH) generates an efficient system to promote the C–H activation of a broad range of heteroarenes.

    3. Superstable Palladium(0) Complex

      Superstable Palladium(0) Complex as an Air- and Thermostable Catalyst for Suzuki Coupling Reactions (pages 60–66)

      Alexandra Jakab, Zoltán Dalicsek, Tamás Holczbauer, Andrea Hamza, Imre Pápai, Zoltán Finta, Géza Timári and Tibor Soós

      Article first published online: 25 NOV 2014 | DOI: 10.1002/ejoc.201403214

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      An unprecedentedly thermo- and air-stable Pd0 complex from readily available electron-poor trifluoromethylated phosphine is reported. The stability of the complex is associated with unusually strong ligand–ligand noncovalent interactions. The unique stability of the complex and the presence of hydrophobic structural elements are exploited in catalytic Suzuki–Miyaura coupling reactions.

    4. Arylation

      Direct Arylation of Imidazo[1,5-a]azines Through Ruthenium and Palladium Catalysis (pages 67–71)

      Daniela Sustac Roman, Valentin Poiret, Guillaume Pelletier and André B. Charette

      Article first published online: 21 NOV 2014 | DOI: 10.1002/ejoc.201403268

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      The RuII-catalyzed direct ortho-arylation of C-3-substituted imidazo[1,5-a]azines with (hetero)aryl halides is investigated. Multiple arylations are performed sequentially in a one-pot procedure with the use of RuII and PdII catalysts.

    5. Asymmetric Alkylation

      Catalytic Asymmetric Alkylation of Aryl Heteroaryl Ketones (pages 72–76)

      Pablo Ortiz, Ana M. del Hoyo and Syuzanna R. Harutyunyan

      Article first published online: 12 NOV 2014 | DOI: 10.1002/ejoc.201403297

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      The first example of the direct catalytic asymmetric alkylation of diaryl ketones by using Grignard reagents is reported. The low reactivity and similarity of the enantiotopic faces of the substrates is partially overcome, which results in the corresponding enantioenriched diarylmethanol core.

    6. Metal-Free Iodination

      Transition-Metal-Free Oxidative Iodination of 1,3,4-Oxadiazoles (pages 77–80)

      Carl Albrecht Dannenberg, Vincent Bizet, Liang-Hua Zou and Carsten Bolm

      Article first published online: 6 NOV 2014 | DOI: 10.1002/ejoc.201403352

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      The transition-metal-free oxidative iodination of 2-substituted 1,3,4-oxadiazoles is developed to provide products in moderate to good yields with NaI as the halogen source and Selectfluor as the oxidant. Neither anhydrous conditions nor an inert atmosphere is required, which renders this process synthetically attractive.

    7. Deoxygenation

      Light-Mediated Deoxygenation of Alcohols with a Dimeric Gold Catalyst (pages 81–85)

      Terry McCallum, Ekaterina Slavko, Mathieu Morin and Louis Barriault

      Article first published online: 12 NOV 2014 | DOI: 10.1002/ejoc.201403351

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      While exploring orthogonal reactivity with [Au2(dppm)2]Cl2 [dppm = 1,1-bis(diphenylphosphino)methane], the high-yielding photochemical bromination of alcohols was found. The simplicity of this reaction makes it a perfect match for combining bromination with reductive dehalogenation through photoredox catalysis. The highly efficient one-pot reductive deoxygenation protocol for primary alcohols is presented.

    8. Reductive Etherification

      Stereoselective Synthesis of cis-2,6-Disubstituted Morpholines and 1,4-Oxathianes by Intramolecular Reductive Etherification of 1,5-Diketones (pages 86–90)

      Santosh J. Gharpure, Dandela Anuradha, Jonnalagadda V. K. Prasad and Pidugu Srinivasa Rao

      Article first published online: 26 NOV 2014 | DOI: 10.1002/ejoc.201403294

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      A simple and efficient, Lewis acid catalysed reductive etherification strategy for the stereoselective synthesis of cis-2,6-disubstituted morpholines and 1,4-oxathianes starting from readily available 1,5-diketones has been developed. The strategy is used in the total synthesis of morpholine-based natural product (±)-chelonin A and a formal total synthesis of (±)-chelonin C.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Microreviews
    7. Short Communications
    8. Full Papers
    1. Donor–Acceptor Systems

      Systematic Variation of Cyanobuta-1,3-dienes and Expanded Tetracyanoquinodimethane Analogues as Electron Acceptors in Photoactive, Rigid Porphyrin Conjugates (pages 91–108)

      Lorenz M. Urner, Michael Sekita, Nils Trapp, W. Bernd Schweizer, Michael Wörle, Jean-Paul Gisselbrecht, Corinne Boudon, Dirk M. Guldi and François Diederich

      Article first published online: 12 NOV 2014 | DOI: 10.1002/ejoc.201403252

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      The modular synthesis and characterization of a series of rigid ZnII porphyrin conjugates is described. The push–pull chromophores incorporated as electron acceptors feature first reduction potentials ranging from –1.78 to –0.58 V vs. Fc+/Fc, and affect the extent of ZnII porphyrin fluorescence quenching according to their acceptor strength.

    2. Fungal Natural Products

      Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris (pages 109–121)

      Tamam El-Elimat, Mario Figueroa, Huzefa A. Raja, Tyler N. Graf, Steven M. Swanson, Joseph O. Falkinham III, Mansukh C. Wani, Cedric J. Pearce and Nicholas H. Oberlies

      Article first published online: 31 OCT 2014 | DOI: 10.1002/ejoc.201402984

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      Sixteen polyketides, six of them new, were isolated from a fungal culture (Setophoma terrestris). Cytotoxicity assays were used to develop structure–activity relationships amongst the series.

    3. Sensors

      Ratiometric Detection of Adenosine-5′-triphosphate (ATP) and Cytidine-5′-triphosphate (CTP) with a Fluorescent Spider-Like Receptor in Water (pages 122–129)

      Abhishek Kumar Gupta, Abhimanew Dhir and Chullikkattil P. Pradeep

      Article first published online: 26 NOV 2014 | DOI: 10.1002/ejoc.201403073

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      A series of water-soluble spider-like receptor molecules has been developed by the Schiff-base condensation of tris(hydroxymethyl)aminomethane (TRIS) with 2,6-diformylphenol (dfp) derivatives. The products could be used for selective fluorescent sensing of adenosine-5-triphosphate (ATP) and cytidine-5′-triphosphate (CTP) in 100 % aqueous media at pH 7.2.

    4. Corrole Synthesis

      Synthesis and Characterization of cis-A2B-Type meso-Triaryl-Substituted Corroles (pages 130–134)

      Shota Ooi, Takayuki Tanaka and Atsuhiro Osuka

      Article first published online: 14 NOV 2014 | DOI: 10.1002/ejoc.201403217

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      A rational synthesis of cis-A2B-type corroles through a [2+2] approach has been developed, which allowed the synthesis of six new corroles in moderate yields. These corroles were structurally well-characterized and their optical and electrochemical properties were also studied.

    5. Peptide Self-Dimerization

      Synthesis of Tetrasubstituted Symmetrical Pyrazines from β-Keto γ-Amino Esters: A Mild Strategy for Self-Dimerization of Peptides (pages 135–141)

      Mothukuri Ganesh Kumar, Varsha J. Thombare, Rupal D. Bhaisare, Anindita Adak and Hosahudya N. Gopi

      Article first published online: 25 NOV 2014 | DOI: 10.1002/ejoc.201403237

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      A facile synthesis of highly symmetrical tetrasubstituted pyrazines through simple aerial oxidation of β-keto γ-esters derived from amino acids and peptides is reported.

    6. Proline Derivatives

      Efficient Synthesis of cis-3-Substituted Prolines by Bidentate-Assisted Palladium Catalysis (pages 142–151)

      Ruokun Feng, Binjie Wang, Yue Liu, Zhanxiang Liu and Yuhong Zhang

      Article first published online: 25 NOV 2014 | DOI: 10.1002/ejoc.201403191

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      A highly effective protocol for the synthesis of C-3-substituted prolines has been developed. Pd-catalyzed C(sp3)–H activation is used for the straightforward functionalization of prolines. The use of an 8-aminoquinolinecarboxamide directing group allows direct arylation, alkenylation, and alkylation at the C-3 position of prolines in moderate to high yields with diverse iodo- or bromo precursors.

    7. Fluorophores

      Rapid Synthesis of Unsymmetrical Sulforhodamines Through Nucleophilic Amination of a Monobrominated Sulfoxanthene Dye (pages 152–165)

      Arnaud Chevalier, Kevin Renault, Frédéric Boschetti, Pierre-Yves Renard and Anthony Romieu

      Article first published online: 5 NOV 2014 | DOI: 10.1002/ejoc.201403165

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      Simplicity and diversity! A range of primary and secondary functionalized amines were easily introduced onto a sulfoxanthene dye through simple metal-free SNAr reactions to provide original sulforhodamine fluorophores with promising properties.

    8. Fluorescent Probes

      A Synthetic Route to 3-(Heteroaryl)-7-hydroxycoumarins Designed for Biosensing Applications (pages 166–^82)

      Benoît Roubinet, Arnaud Chevalier, Pierre-Yves Renard and Anthony Romieu

      Article first published online: 21 NOV 2014 | DOI: 10.1002/ejoc.201403215

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      A condensation reaction between 7-acetoxy-3-formylcoumarin and various C- and/or N-monosubstituted ortho-phenylendiamine derivatives has led to a new class of 3-(heteroaryl)-7-hydroxycoumarins meeting the requirements for biosensing applications (bioconjugation ability, water solubility, and high “fluorogenic” reactivity).

    9. Macrocycles

      Multigram Four-Step Synthesis of 1,4,7-Triazacyclononanes with 2Ra/Rb N-Functionalization Pattern by Starting from Diethylenetriamine (pages 183–^87)

      Guillaume Gros and Jens Hasserodt

      Article first published online: 21 NOV 2014 | DOI: 10.1002/ejoc.201402821

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      A four-step synthetic route to 1,4,7-triazacyclononanes with a 2Ra/Rb N-functionalization pattern is presented. The formation of the macrocycle is greatly facilitated by the use of an organic template. This allows for the atom-economic, multigram syntheses of several substituted derivatives with excellent overall yields in less than five days.

    10. Thioacetal Cleavage

      An Organocatalytic Process for the Hydrolytic Cleavage of Dithianes Mediated by Imidazolium Ions: No Harsh Agents Required (pages 188–194)

      Lauren Myles, Nicholas Gathergood and Stephen J. Connon

      Article first published online: 26 NOV 2014 | DOI: 10.1002/ejoc.201402947

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      A new, organocatalytic approach to the hydrolytic deprotection of dithianes has been developed involving a low-toxicity imidazolium-ion-based catalyst in an aqueous medium.

    11. Peptide Antibiotics

      Synthesis of Mono and Bis[60]fullerene-Based Dicationic Peptoids (pages 195–201)

      Sreenu Jennepalli, Katherine A. Hammer, Thomas V. Riley, Stephen G. Pyne and Paul A. Keller

      Article first published online: 21 NOV 2014 | DOI: 10.1002/ejoc.201403046

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      [60]Fullerenyldihydropyrrole peptides were prepared from the coupling of mono and bis[60]fullerenyldihydropyrrolecarboxylic acids with peptides to produce a series of fullerenyl-anchored tetra- and penta-peptides. Their synthesis and characterisation are discussed in this paper.

    12. Drug Conjugates

      Synthesis and Cytotoxic Activity of Self-Assembling Squalene Conjugates of 3-[(Pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one Anticancer Agents (pages 202–212)

      Eric Buchy, Sabrina Valetti, Simona Mura, Julie Mougin, Claire Troufflard, Patrick Couvreur and Didier Desmaële

      Article first published online: 21 NOV 2014 | DOI: 10.1002/ejoc.201403088

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      New squalene conjugates of antiangiogenic 3-(pyrrolyl)methylidenyl-substituted oxindoles sunitinib and semaxanib were synthesized. Strategies to link squalene to the oxindole nitrogen through a pH-sensitive linker are presented. These squalenoyl prodrugs self-assemble into nanoparticles of about 150 nm in size, and show notable cytotoxicity on the human umbilical vein endothelial cell line

    13. Carbonylation

      Synthesis of Vinyl- and Aryl–Acyl Sulfonimidamides Through Pd-Catalyzed Carbonylation Using Mo(CO)6 as ex situ CO Source (pages 213–219)

      Prasad B. Wakchaure, Sanjay R. Borhade, Anja Sandström and Per I. Arvidsson

      Article first published online: 19 NOV 2014 | DOI: 10.1002/ejoc.201403148

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      N-(α,β-Unsaturated acyl) sulfonimidamides have been prepared through a Pd-catalyzed carbonylation protocol, employing sulfonimidamide nucleophiles, CO gas released ex situ, and vinyl/aryl halides and triflates as reagents. The obtained products undergo facile thermolytic Boc deprotection in DMSO, thereby offering convenient access to deprotected analogues.

    14. Gold Catalysts

      Ammonium-Salt-Tagged IMesAuCl Complexes and Their Application in Gold-Catalyzed Cycloisomerization Reactions in Water (pages 220–225)

      Katrin Belger and Norbert Krause

      Article first published online: 12 NOV 2014 | DOI: 10.1002/ejoc.201403153

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      The total synthesis of water-soluble ammonium-salt-tagged NHC–gold complexes is described, as well as their application in aqueous media and their recyclability.

    15. Cycloaddition Reactions

      The First Bidirectional [4+2] Cycloadditions of Benzo[1,2:4,5]dicyclobutenes: Synthesis of Benzo[1,2-f:4,5-f′]diisoindole-1,3,7,9-tetraones (pages 226–234)

      Ismail Abdelshafy Abdelhamid and Holger Butenschön

      Article first published online: 5 NOV 2014 | DOI: 10.1002/ejoc.201403247

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      A bidirectional sequence of electrocyclic ring opening, [4+2] cycloaddition, methanol elimination, and dehydrogenation allows the formation of benzo[1,2-f:4,5-f′]diisoindole-1,3,7,9-tetraones from benzo[1,2:4,5]dicyclobutenes.

    16. Organometallic Addition

      Addition of Vinylmetallic Reagents to Chiral 2-Formyltetrahydrofuran (pages 235–241)

      Janire Lamariano-Merketegi, Adriana Lorente, Alejandro Gil, Fernando Albericio and Mercedes Álvarez

      Article first published online: 17 NOV 2014 | DOI: 10.1002/ejoc.201402987

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      A chelation-controlled addition, a carboalumination, and a Nozaki–Hiyama–Kishi (NHK) reaction were used to study the stereoselective addition of vinylmetallic reagents to enantiopure trisubstituted 2-formyl-tetrahydrofuran compounds. The optimal conditions for the carboalumination and NHK reactions provided satisfactory yields and diastereoselectivities.

    17. Fused Porphycenes

      Dibenzoporphycene – Platform for the Generation of Fused Porphycenes (pages 242–246)

      Wolfgang Brenner and Norbert Jux

      Article first published online: 25 NOV 2014 | DOI: 10.1002/ejoc.201403067

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      A fused porphycene is generated through a shortened synthetic route. This molecule will serve as a starting point for the synthesis of larger fused porphycenes.

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