European Journal of Organic Chemistry

Cover image for Vol. 2016 Issue 4

February 2016

Volume 2016, Issue 4

Pages 608–854

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. News
    4. Microreview
    5. Communications
    6. Full Papers
    1. You have free access to this content
      Room-Temperature Alkynylation of Phosphine Oxides with Copper Acetylides: Practical Synthesis of Alkynylphosphine Oxides (Eur. J. Org. Chem. 4/2016)

      Phidéline Gérard, Romain Veillard, Carole Alayrac, Annie-Claude Gaumont and Gwilherm Evano

      Article first published online: 5 FEB 2016 | DOI: 10.1002/ejoc.201690006

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      The cover picture shows the alkynylation of phosphine oxides with copper acetylides. These polymeric, rock-stable and unreactive reagents can be readily activated by coordination with simple ligands and oxidation with molecular oxygen. This activation enables the in situ generation of highly reactive, oxidized copper acetylides that can be trapped by a series of phosphine oxides to give, after a formal reductive elimination step, the corresponding alkynylation product, i.e., alkynylphosphine oxides, which can be readily and easily obtained at room temperature by this mix-and-stir process. Details are discussed in the Communication by C. Alayrac, A.-C. Gaumont, G. Evano et al. on p. 633 ff.

  2. News

    1. Top of page
    2. Cover Picture
    3. News
    4. Microreview
    5. Communications
    6. Full Papers
  3. Microreview

    1. Top of page
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    3. News
    4. Microreview
    5. Communications
    6. Full Papers
    1. Sustainable Chemistry

      Deep Eutectic Solvents: The Organic Reaction Medium of the Century (pages 612–632)

      Diego A. Alonso, Alejandro Baeza, Rafael Chinchilla, Gabriela Guillena, Isidro M. Pastor and Diego J. Ramón

      Article first published online: 5 JAN 2016 | DOI: 10.1002/ejoc.201501197

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      21st Century DESs: Worries about the sustainability of our civilization on Earth are forcing changes on all aspects of industrial production. In organic synthesis, solvents (including their production and degradation) are the main waste component in reactions. Deep eutectic solvents (and related mixtures) offer an irresistible opportunity to improve the sustainability of processes in this century.

  4. Communications

    1. Top of page
    2. Cover Picture
    3. News
    4. Microreview
    5. Communications
    6. Full Papers
    1. Alkynylphosphine Oxide Synthesis

      Room-Temperature Alkynylation of Phosphine Oxides with Copper Acetylides: Practical Synthesis of Alkynylphosphine Oxides (pages 633–638)

      Phidéline Gérard, Romain Veillard, Carole Alayrac, Annie-Claude Gaumont and Gwilherm Evano

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501440

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      An efficient procedure involving the oxidative alkynylation of secondary phosphine oxides with copper acetylides for the synthesis of alkynylphosphine oxides is reported. Activation with molecular oxygen in the presence of simple additives enables the formal umpolung of the poorly nucleophilic copper acetylides, which can be coupled with phosphine oxides under remarkably mild conditions; DMI = 1,2-dimethylimidazole, NMI = N-methylimidazole.

    2. 2-Aminoimidazole Alkaloids

      Lissodendrins A and B: 2-Amino­imidazole Alkaloids from the Marine Sponge Lissodendoryx (Acanthodoryx) fibrosa (pages 639–643)

      Amin Mokhlesi, Rudolf Hartmann, Elisabeth Achten, Chaidir, Thomas Hartmann, Wenhan Lin, Georgios Daletos and Peter Proksch

      Article first published online: 10 DEC 2015 | DOI: 10.1002/ejoc.201501250

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      Two new 2-aminoimidazole alkaloids, lisodendrins A and B, were isolated from the EtOAc extract of the sponge Lissodendoryx (Acanthodoryx) fibrosa collected in Indonesia. Lissodendrins A and B possess unprecedented skeletons, and the long-range HMBC NMR experiment proved to be a valuable tool for establishing the structures of these compounds. A rationale for the biosynthesis of the new metabolites is likewise discussed.

    3. Sesquiterpene Synthesis

      Rapid and Scalable Synthesis of cis-Fused Guaiane-Type Sesquiterpenes (pages 644–646)

      Christelle Serba, Roman Lagoutte and Nicolas Winssinger

      Article first published online: 12 JAN 2016 | DOI: 10.1002/ejoc.201501277

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      A rapid entry into the cis-fused bicyclic guaiane framework and elaboration into sesquiterpene-related compounds is reported. The formation of the cis-fused bicyclic system benefits from a stereoconvergent sulfoxide elimination.

    4. Fused-Ring Systems

      Double π-Bond Isomerization/Friedel–Crafts Reaction Involving γ-­Amidocronates: Access to γ-Aryl/Heteroaryl GABA Scaffolds and Dihydropyrido[1,2-a]indoles (pages 647–653)

      Anvita Srivastava and Sampak Samanta

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501388

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      A one-pot, two-step sequential process is developed to access γ-heteroaryl/aryl-substituted GABA analogues in good to high combined yields by π-bond isomerization of N-benzoyl (Bz)-protected γ-aminocrotonates by using Et3N, followed by tandem π-bond isomerization/Friedel–Crafts reaction of the resultant enamines with several heteroarenes/arenes by using B(C6F5)3 as a Lewis acid catalyst; Cbz = benzyloxycarbonyl.

    5. Total Synthesis

      A Concise Total Synthesis of the Stereoisomers of (–)-Pochonicine (pages 654–657)

      Rahul Vilas Salunke and Namakkal G. Ramesh

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501413

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      Chemoselective debenzylation of a primary benzyloxy group and an unprecedented Na–Hg-mediated concomitant N-detosylative intramolecular epoxide ring-opening reaction allow the total synthesis of the four stereoisomers of (–)-pochonicine. Additional steps for the protection of other functional groups are not required. These compounds are inhibitors of β-N-acetylglucosaminidase.

    6. 1,2-Diones

      Copper-Assisted Synthesis of 2-Hydroxyphenyl-1,2-diones from Phenols and 2-Oxoaldehydes (pages 658–662)

      Narsaiah Battini, Satyanarayana Battula and Qazi Naveed Ahmed

      Article first published online: 18 JAN 2016 | DOI: 10.1002/ejoc.201501423

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      An efficient copper(II)-catalyzed protocol for the ortho-functionalization of phenols is developed. This method tolerates a wide variety of 2-oxoaldehydes and phenols and affords the corresponding 2-hydroxyphenyl-1,2-diones in appreciable yields.

    7. Oxidative Heck Coupling

      Oxypalladation Initiating the Oxid­ative Heck Reaction with Alkenyl ­Alcohols: Synthesis of Isocoumarin–Alkanones (pages 663–667)

      Meifang Zheng, Liangbin Huang, Qizhen Tong, Wanqing Wu and Huanfeng Jiang

      Article first published online: 5 JAN 2016 | DOI: 10.1002/ejoc.201501451

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      Regioselective nucleopalladation initiated oxidative Heck coupling between internal alkynes and alkenyl alcohols by using oxygen as the sole oxidant is reported. This protocol tolerates a wide range of functional groups and can be performed with unactivated alkenes to afford isocoumarin alkanones.

    8. 1,3-Dipolar Cycloaddition

      Azide–Enolate 1,3-Dipolar Cycloaddition as an Efficient Approach for the Synthesis of 1,5-Disubstituted 1,2,3-Triazoles from Alkyl/Aryl Azides and β-Ketophosphonates (pages 668–672)

      Davir González-Calderón, Aydeé Fuentes-Benítes, Eduardo Díaz-Torres, Carlos A. González-González and Carlos González-Romero

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501465

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      A simple and efficient approach to obtain 1,5-disubstituted 1,2,3-triazoles through a highly regioselective synthesis is developed. Coupling through 1,3-dipolar cycloaddition of aryl/alkyl azides and β-ketophosphonates is promoted by KOH in reagent-grade solvents (acetonitrile or tetrahydrofuran) with good to excellent yields.

    9. Boronic Esters

      You have full text access to this OnlineOpen article
      Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Amino­alkyl)boronic Esters (pages 673–677)

      Nina Ursinyova, Robin B. Bedford and Timothy Gallagher

      Article first published online: 23 DEC 2015 | DOI: 10.1002/ejoc.201501492

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      Copper-catalyzed borylation of 1,2- and 1,3-cyclic sulfamidates provides stereochemically defined (β- and γ-aminoalkyl)boronate esters; iodide is essential but borylation is accelerated by the presence of the N-sulfate moiety.

    10. Chemiluminescence

      The Light Emitter of the 2-Coumar­anone Chemiluminescence: Theoretical and Experimental Elucidation of a Possible Model for Bioluminescent Systems (pages 678–681)

      Stefan Schramm, Isabelle Navizet, Panče Naumov, Naba K. Nath, Romain Berraud-Pache, Pascal Oesau, Dieter Weiss and Rainer Beckert

      Article first published online: 12 JAN 2016 | DOI: 10.1002/ejoc.201501515

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      The reaction mechanism of 2-coumaranones, a new class of synthetically accessible strongly chemiluminescent materials that mimic the bioluminescence reaction, is reported. The pathways of chemiexcitation and photorelaxation are clarified on the basis of synthetic evidence and spectrochemical and computational mechanistic analysis.

    11. Click Chemistry

      An Efficient and Tunable Route to Bis(1,2,3-triazol-1-yl)methane-Based Nitrogen Compounds (pages 682–687)

      José A. Castro-Osma, Agustín Lara-Sanchez, Antonio Otero, Ana M. Rodríguez, María C. de la Torre and Miguel A. Sierra

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501519

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      A new approach for the preparation of diverse and complex bis(1,2,3-triazol-1-yl)methane derivatives is reported. This process exhibits excellent compatibility with different functionalized gem-diazides and different substituted terminal alkynes.

    12. Natural Products Synthesis

      Enantioselective Total Synthesis of the Proposed Structure of the Endophytic Fungal Metabolite Phomolide G: Structural Revision and Unambiguous Stereochemical Assignment (pages 688–692)

      James McNulty, David McLeod and Hilary A. Jenkins

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501592

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      A total synthesis of the proposed structure of the natural macrolactone Phomolide G by a bidirectional strategy from L-tartaric acid is reported. Its structure was confirmed by X-ray analysis and chemical correlations, which did not match the data of natural Phomolide G. Modifications to this synthesis allowed access to the C3-epimer, the 1H and 13C NMR spectroscopic data of which are in full accord with that reported for the natural product.

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. News
    4. Microreview
    5. Communications
    6. Full Papers
    1. Enantiopure 1,5-Amino Alcohols

      A General Method for the Synthesis of Enantiopure 1,5-Amino Alcohols (pages 693–703)

      Guillaume Guignard, Núria Llor, Aina Urbina, Joan Bosch and Mercedes Amat

      Article first published online: 21 DEC 2015 | DOI: 10.1002/ejoc.201501409

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      A general method for the synthesis of diversely substituted enantiopure 5-amino-1-pentanols is described. The key step is an LiNH2BH3-promoted reductive opening of (R)-phenylglycinol-derived oxazolopiperidone lactams.

    2. All-Carbon Quaternary Stereocenters

      Enantioselective Construction of Aryl-Substituted All-Carbon Quaternary Stereocenters by Using Tertiary Amine–Thiourea-Catalyzed Michael Additions (pages 704–715)

      Peng Chen, Xu Bao, Le-Fen Zhang, Guo-Jie Liu and Yi-Jun Jiang

      Article first published online: 5 JAN 2016 | DOI: 10.1002/ejoc.201501420

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      Multifunctionalized compounds with aryl-substituted all-carbon quaternary stereocenters were obtained by the enantioselective Michael addition of α-cyano ketones and acrylates using a chiral tertiary amine-thiourea catalyst. The low-cost, metal-free reaction can tolerate multiple functional groups, and the Michael adducts are potential precursors for a number of hydrodibenzofuran natural products.

    3. Cycloaddition

      Penta-2,4-dien-1-ones by Formal [3+2] Cycloaddition–Rearrangement of Electron-Deficient Diethyl 2-(Dicyanomethylene)malonate with Alk­ynes (pages 716–724)

      Etienne J. Donckele, Tristan A. Reekie, Nils Trapp and François Diederich

      Article first published online: 5 JAN 2016 | DOI: 10.1002/ejoc.201501473

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      Formal [3+2] cycloaddition–rearrangement cascades from moderately activated to unactivated alkynes and electron-deficient diethyl 2-(dicyanomethylene)malonate yield a variety of substituted penta-2,4-dien-1-ones. This transformation proceeds with excellent regioselectivity and with a wide range of alkynes without a catalyst. A mechanism for the formation of the nonplanar chromophores is proposed.

    4. Stereoenriched Biphenyls

      Access to Atropisomerically En­riched Biaryls by the Coupling of Aryllithiums with Arynes under Control by Homochiral Oxazolines (pages 725–732)

      Boubacar Yalcouye, Anaïs Berthelot-Bréhier, David Augros, Armen Panossian, Sabine Choppin, Matthieu Chessé, Françoise Colobert and Frédéric R. Leroux

      Article first published online: 23 DEC 2015 | DOI: 10.1002/ejoc.201501503

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      We report the preparation of axially stereoenriched biphenyls by the coupling of in situ generated aryllithiums and arynes using chiral oxazoline auxiliaries. The design of the aryne precursors, the choice of oxazoline and the reaction conditions were key to accessing the desired, highly substituted, atropisomerically enriched biaryl products.

    5. Donor–Acceptor Systems

      Tuning of the HOMO–LUMO Gap of Symmetrical and Unsymmetrical Ferrocenyl-Substituted Diketopyrrolopyrroles (pages 733–738)

      Yuvraj Patil, Thaksen Jadhav, Bhausaheb Dhokale and Rajneesh Misra

      Article first published online: 17 DEC 2015 | DOI: 10.1002/ejoc.201501123

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      Symmetrical and unsymmetrical π-bridged donor–acceptor (D–π–A) ferrocenyl-diketopyrrolopyrrole (DPPs) frameworks were synthesized by a Pd-catalyzed Sonogashira cross-coupling and [2+2] cycloaddition–retroelectrocyclization reactions. The tetracyanobutadiene (TCBD) DPPs 7 and 8 have lower HOMO–LUMO gap values relative to those of ethyne-bridged ferrocenyl-DPPs 5 and 6.

    6. Isocoumarin-Fused Enediynes

      Towards Isocoumarin-Fused Enediyne Systems through the Electrophilic Cyclization of Methyl o-(Buta-1,3-diynyl)benzoates (pages 739–747)

      Natalia A. Danilkina, Larisa Y. Gurskaya, Aleksander V. Vasilyev and Irina A. Balova

      Article first published online: 21 DEC 2015 | DOI: 10.1002/ejoc.201501262

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      An approach based on the electrophilic cyclization of methyl o-(buta-1,3-diynyl)benzoates followed by the Sonogashira coupling of 3-ethynyl-4-iodoisocoumarins with acetylenes proved to be highly efficient for the synthesis of enediyne systems fused to an isocoumarin core. The approach proposed allowed different substituents to be introduced to both ethynyl moieties with complete regiocontrol.

    7. Bacterial O-Antigens

      Structural and Conformational Study of the O-Antigenic Portion of the Lipopolysaccharide Isolated from Burkholderia gladioli pv. cocovenenans (pages 748–755)

      Antonia De Felice, Alba Silipo, Kirstin Scherlach, Claudia Ross, Christian Hertweck and Antonio Molinaro

      Article first published online: 4 JAN 2016 | DOI: 10.1002/ejoc.201501308

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      B. gladioli pv. cocovenenas is a plant-pathogenic bacterium isolated from mucoralean fungus Rhizopus microsporus var. oligosporus. We have determined the structure and spatial arrangement of the O-polysaccharide portions of the lipopolysaccharide.

    8. Anthraquinone Imine Dyes

      Optical and Electrochemical Properties of Anthraquinone Imine Based Dyes for Dye-Sensitized Solar Cells (pages 756–767)

      Christian Prinzisky, Ingo Meyenburg, Andreas Jacob, Benjamin Heidelmeier, Fabian Schröder, Wolfram Heimbrodt and Jörg Sundermeyer

      Article first published online: 16 DEC 2015 | DOI: 10.1002/ejoc.201501309

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      Ten anthraquinone and anthraquinone imine based dyes have been synthesized and characterized by XRD and electrochemical investigations as well as by optical and photoluminescence (PL) spectroscopy. The PL spectra show that crystal formation results in redshifted spectra and a strong polarization of the excitonic absorption spectra.

    9. Decarboxylative C–N Bond Formation

      One-Pot Transformation of Aliphatic Carboxylic Acids into N-Alkylsuccin­imides with NIS and NCS/NaI (pages 768–772)

      Yuhta Nakai, Katsuhiko Moriyama and Hideo Togo

      Article first published online: 15 DEC 2015 | DOI: 10.1002/ejoc.201501315

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      Various primary aliphatic carboxylic acids were treated with NIS or NCS/NaI in 1,2-dichloroethane, followed by the reaction with K2CO3 in acetone to give N-alkylsuccinimides in one pot. A semi-large-scale transformation of aliphatic carboxylic acid into N-alkylsuccinimide and primary alkylamine was also carried out successfully.

    10. Silyl Enol Ethers

      From Protected β-Hydroxy Acylsil­anes to Functionalized Silyl Enol Ethers and Applications in Mukaiyama Aldol Reactions (pages 773–779)

      Johal Ruiz, Nagaraju Karre, Thierry Roisnel, Srivari Chandrasekhar and René Grée

      Article first published online: 5 JAN 2016 | DOI: 10.1002/ejoc.201501344

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      E or Z enol ethers have been prepared in a stereoselective manner from protected β-hydroxy acylsilanes. For these enol ethers, the nature of the silyl substituent plays a key role in the stereoselectivity of the Mukaiyama aldol reaction.

    11. Amide Synthesis

      Nickel-Catalyzed Reductive Addition of Aryl/Benzyl Halides and Pseudohalides to Carbodiimides for the Synthesis of Amides (pages 780–788)

      Farhad Panahi, Fereshteh Jamedi and Nasser Iranpoor

      Article first published online: 23 DEC 2015 | DOI: 10.1002/ejoc.201501349

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      A new approach was developed for the synthesis of amide derivatives using a reductive nickel-catalyzed coupling reaction between benzyl/aryl electrophiles and carbodiimides. Carbodiimides were introduced as new coupling partners. This protocol resulted in the formation of a range of amides after hydrolysis of the amidine product.

    12. Recyclable Heck Catalyst

      Palladium(II) Complexes of the Hemilabile Pincer Ligand PPh(o-C6H4SMe)2 as Highly Active and Recyclable ­Mizoroki–Heck Catalysts (pages 789–798)

      Asunción Luquin, Noelia Castillo, Elena Cerrada, Francisco L. Merchan, Julian Garrido and Mariano Laguna

      Article first published online: 15 DEC 2015 | DOI: 10.1002/ejoc.201501354

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      PdII complexes with PPh(o-C6H4SMe)2 acting as a pincer ligand in an S,S′,P- or S,P-coordination mode, have been synthesized. The insertion of CO into the Pd–Me bond of these complexes was tested. Some of the complexes obtained are good Mizoroki–Heck catalysts. The catalyst can be retained on a silica gel column, recovered, and reused several times without losing activity.

    13. Organic Solar Cells

      Starburst Triphenylamine-Based Donor–Acceptor-Type Small Molecules for Solution-Processed Organic Solar Cells (pages 799–805)

      Hua Tan, Wenhong Peng, Manjun Xiao, Chao Xu, Kaixuan Nie, Junting Yu, Yafei Wang, Yu Liu and Weiguo Zhu

      Article first published online: 23 DEC 2015 | DOI: 10.1002/ejoc.201501376

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      Two novel donor–acceptor molecules, DTPA-DPP and TTPA-DPP, are synthesized. These compounds with a starburst configuration show good light-harvesting properties and charge-transport properties. The TTPA-DPP-based organic solar cells exhibit the best photovoltaic properties with a power conversion efficiency of 2.47 %.

    14. Modular Oxindole Synthesis

      Modular Catalytic Synthesis of 3-Amino-3-aryl-2-oxindoles: Rh Catalysis with Isatin-Derived N-Boc-Protected Ketimines (pages 806–812)

      Carolina S. Marques and Anthony J. Burke

      Article first published online: 23 DEC 2015 | DOI: 10.1002/ejoc.201501399

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      A general and economically viable route for the synthesis of 3-amino-3-aryl-2-oxindole compounds was accomplished through the Rh-catalysed addition of arylboronic acids to isatin-derived N-tert-butoxycarbonyl-protected ketimines.

    15. Catalytic Cavitands

      Introverted Phosphorus-Au Cavitands for Catalytic Use (pages 813–820)

      Michael P. Schramm, Mao Kanaura, Kouhei Ito, Masataka Ide and Tetsuo Iwasawa

      Article first published online: 15 DEC 2015 | DOI: 10.1002/ejoc.201501426

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      Preparative synthesis of introverted phosphorus cavitands is achieved, and subsequent complexation with AuCl-enabled crystallographic analysis. The inwardly oriented Au was proven to have catalytic properties and may provide new and great opportunities for supramolecular catalysis.

    16. Fluorescent Probes

      Fluorescent Probes from Stable Aromatic Nitrile Oxides (pages 821–829)

      Luigi Ferdinando Minuti, Misal Giuseppe Memeo, Stefano Crespi and Paolo Quadrelli

      Article first published online: 23 DEC 2015 | DOI: 10.1002/ejoc.201501478

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      Stable aromatic nitrile oxides underwent a 1,3-dipolar cycloaddition reaction with 1-iodo-4-(prop-2-yn-1-yloxy)benzene to afford the expected isoxazoles in very good yields as single regioisomers. The reductive cleavage of the N–O bond and complexation with BF3·Et2O afforded the corresponding boron complexes, which are promising fluorescent probes.

    17. Ylide Mechanisms

      Mechanism of Ylide Transfer to ­Carbonyl Compounds: Density Functional Calculations (pages 830–839)

      Mahendra Patil and Walter Thiel

      Article first published online: 23 DEC 2015 | DOI: 10.1002/ejoc.201501073

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      Density functional calculations for the mechanism of ylide transfer favor different pathways for different sulfur reagents.

    18. Helical Handedness

      Handedness Preferences of Heterochiral Helical Peptides Containing Homochiral Peptide Segments (pages 840–846)

      Yosuke Demizu, Hiroko Yamashita, Takashi Misawa, Mitsunobu Doi, Makoto Oba, Masakazu Tanaka and Masaaki Kurihara

      Article first published online: 5 JAN 2016 | DOI: 10.1002/ejoc.201501146

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      Attaching a homochiral L-Leu-L-Leu-Aib segment to the C-termini of heterochiral peptides with the structure (D-Leu-L-Leu-Aib)n has a greater influence on helical handedness than does tethering of the same segment to heterochiral peptide N-termini.

    19. Oxidative Cycloaddition

      Copper Acetate Catalyzed Regio­selective Synthesis of Substituted 1,2,3-Triazoles: A Versatile Azide–Alk­ene Cycloaddition/Oxidation Approach (pages 847–854)

      Sandeep Rohilla, Shyam Sunder Patel and Nidhi Jain

      Article first published online: 23 DEC 2015 | DOI: 10.1002/ejoc.201501301

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      1,4-Disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles have been synthesized with high regioselectivity through an oxidative cycloaddition approach. The method, which uses copper acetate as an inexpensive catalyst and air as the oxidant, is highly versatile and works well for the reaction of benzylic and aryl azides with terminal and internal olefins that contain electron-withdrawing groups.

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