Asian Journal of Organic Chemistry

Cover image for Vol. 3 Issue 7

Early View (Online Version of Record published before inclusion in an issue)

Managing Editor: Richard Threlfall; Editorial Board Chairs: Sung Ho Kang, Keiji Maruoka, Deqing Zhang

Online ISSN: 2193-5815

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

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  1. 1 - 20
  1. Communications

    1. Solar Cells

      Function of CH2 Addends on 54π Fullerene Acceptors

      Shan Chen, Zuo Xiao, Dan He, Lina Ma and Prof. Liming Ding

      Article first published online: 24 JUL 2014 | DOI: 10.1002/ajoc.201402104

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      Me two! Stepwise replacement of o-quinodimethane addends to 54π fullerenes with CH2 addends improves electron mobility of fullerene, enhances crystallinity of poly(3-hexylthiophene), increases the number of donor-acceptor interfaces, and reduces bimolecular recombination, thus enhancing the power conversion efficiency of fullerene:P3HT solar cells remarkably from 2.26 % to 6.25 %.

  2. Full Papers

    1. Domino Reactions

      Domino Knoevenagel Condensation/Aza-Ene Addition/N-Cyclization Route to Functionalized Imidazo[1,2-a]pyridines and Pyrido[1,2-a]pyrimidines

      Sathiyamoorthi Sivakumar and Raju Ranjith Kumar

      Article first published online: 23 JUL 2014 | DOI: 10.1002/ajoc.201402100

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      One-pot wonder! The syntheses of imidazo[1,2-a]pyridines and pyrido[1,2-a]pyrimidines were carried out by using a one-pot three-component protocol. The reaction proceeds in a single step through a domino Knoevenagel condensation/aza-ene addition/imine–enamine tautomerization/chemoselective N-cyclization sequence of reactions (In=indolyl).

  3. Focus Reviews

    1. Aziridine Chemistry

      Application of Regio- and Stereoselective Functional Group Transformations of Chiral Aziridine-2-carboxylates

      Prof. Dr. Hyun-Joon Ha, Jae-Hoon Jung and Prof. Dr. Won Koo Lee

      Article first published online: 23 JUL 2014 | DOI: 10.1002/ajoc.201402098

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      Boxing clever: This Focus Review highlights the chemistry of chiral aziridine-2-carboxylates as building blocks based on regio- and stereoselective functional group transformations of the carboxylate group and aziridine ring. This chemistry is exemplified by the efficient and highly stereoselective synthesis of many biologically important amines, including several natural products.

  4. Full Papers

    1. Lanthanide Catalysis

      Upward Trend in Catalytic Efficiency of Rare-Earth Triflate Catalysts in Friedel–Crafts Aromatic Sulfonylation Reactions

      Vo Thu An Nguyen, Prof. Dr. Fritz Duus and Prof. Dr. Thach Ngoc Le

      Article first published online: 22 JUL 2014 | DOI: 10.1002/ajoc.201402067

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      Going up! The upward trend in efficiency of lanthanide (Ln) triflates in catalyzing aromatic sulfonylation reaction correlates with the lanthanide sequence in the periodic table. Various related physical properties of lanthanide ions were found to have some influence on the catalytic activity.

    2. Synthetic Methods

      One-Pot Copper-Catalyzed Aerobic Decarboxylative Coupling of Phenylacetic Acids with o-Aminobenzenes and Dioxygen as the Oxidant Leading to Benzoxazoles and Benzothiazoles

      Daoshan Yang, Kelu Yan, Wei Wei, Laijin Tian, Yuanyuan Shuai, Ruixia Li, Jinmao You and Prof. Hua Wang

      Article first published online: 22 JUL 2014 | DOI: 10.1002/ajoc.201402085

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      A fair cop: A copper-catalyzed synthesis of benzoxazole and benzothiazole derivatives via cascade reactions of substituted o-aminobenzenes with phenylacetic acids under dixoygen has been developed. The method is practical and the starting materials are readily available. These advantages provide an opportunity for the construction of diverse and useful benzoxazole and benzothiazole motifs within organic, medicinal, and materials chemistry

    3. Solar Cells

      A Ruthenium-Based Light-Harvesting Antenna Bearing an Anthracene Moiety in Dye-Sensitized Solar Cells

      Dr. Georgios C. Vougioukalakis, Dr. Maria Konstantakou, Dr. Eleftherios K. Pefkianakis, Antonios N. Kabanakis, Dr. Thomas Stergiopoulos, Dr. Athanassios G. Kontos, Dr. Aikaterini K. Andreopoulou, Prof. Dr. Joannis K. Kallitsis and Dr. Polycarpos Falaras

      Article first published online: 14 JUL 2014 | DOI: 10.1002/ajoc.201402096

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      Ru-thlessly efficient: A heteroleptic ruthenium-based light-harvesting antenna coordinated with a phenylanthracene-substituted terpyridine, a bipyridine, and a NCS ligand was synthesized. TiO2 films sensitized by this photosensitizer were studied through various techniques. The photosensitizer was evaluated in I/I3-based liquid electrolyte dye-sensitized solar cells, affording overall power conversion efficiencies up to 3.75 %.

  5. Focus Reviews

    1. Fluorescent Probes

      Fluorescent Probes for Hydrogen Sulfide Detection

      Bo Peng and Prof. Ming Xian

      Article first published online: 2 JUL 2014 | DOI: 10.1002/ajoc.201402064

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      Probing for a pong? Hydrogen sulfide (H2S) is an important signaling molecule with potent cytoprotective actions. The detection of H2S in biological samples is still a challenge. In this Focus Review, we provide an overview of current progress in fluorescence measurements for H2S. The development and properties of some representative reaction-based H2S fluorescent probes are discussed.

  6. Communications

    1. Hypervalent Iodine | Very Important Paper

      A Practical Approach for the Oxidation of Unactivated Csp3[BOND]H Bonds with o-Nitro(diacetoxyiodo)benzene as an Efficient Hypervalent Iodine(III)-Based Oxidizing Agent

      Dr. Shin A. Moteki, Sermadurai Selvakumar, Tiexin Zhang, Asuka Usui and Prof. Dr. Keiji Maruoka

      Article first published online: 2 JUL 2014 | DOI: 10.1002/ajoc.201402087

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      A bit hyper: A practical approach for the oxidation of unactivated Csp3[BOND]H bonds by o-nitro(diacetoxyiodo)benzene is presented. The nitro group coordinates to the adjacent iodine center through dipolar interaction, which leads to a single substitution of the acetate ligand by tert-butyl hydroperoxide (TBHP). As a result, a strong iodanyl radical is formed, which can activate the inert Csp3[BOND]H bonds in a highly efficient manner.

  7. Focus Reviews

    1. Photochemistry

      Light-Controlled Chemical Reactions and Their Applications in Biological Systems

      Prof. Jeeyeon Lee

      Article first published online: 30 JUN 2014 | DOI: 10.1002/ajoc.201402054

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      This Focus Review describes recent efforts in developing light-controlled switchable compounds and their applications in biological systems. In particular, photoisomerization reactions of azobenzene as well as synthetic green fluorescent protein chromophores are discussed.

  8. Full Papers

    1. Solar Cells

      A Solution-Processed Small-Molecule Diketopyrrolopyrrole Dimer for Organic Solar Cells

      Zhixiao Niu, Xue Wang, Dr. Jianhua Huang, Ailing Tang, Prof. Yuxi Sun and Prof. Chuanlang Zhan

      Article first published online: 26 JUN 2014 | DOI: 10.1002/ajoc.201402048

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      A diketopyrrolopyrrole (DPP) dimer is synthesized by combining electron-rich benzodithiophene-thiophene and electron-deficient DPP. It has energy levels what match with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) and a broad UV/vis absorption spectrum. With PC71BM as the acceptor, the power conversion efficiency is 3.90 %, the short-circuit current density is 9.85 mA cm−2, the open-circuit voltage is 0.71 V, and the fill factor is 0.57.

  9. Communications

    1. N-Heterocyclic Carbenes

      Enantioselective Syntheses of α-Silyl Amines via a Copper-N-Heterocyclic Carbene Catalyzed Nucleophilic Silicon Transfer to Imines

      Chunliang Zhao, Chenran Jiang, Jing Wang, Cai Wu, Dr. Qing-Wei Zhang and Prof. Dr. Wei He

      Article first published online: 20 JUN 2014 | DOI: 10.1002/ajoc.201402077

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      A-sil-ectric: An efficient method for the enantioselective syntheses of biologically interesting α-silyl amines was developed. This method features good yields of 77–93 %, high enantioselectivity of 79–99 % ee, a commercially available Si[BOND]B reagent, and an easily accessible chiral monodentate N-heterocyclic carbene (NHC) ligand. Ts=4-toluenesulfonyl.

    2. Annulation

      Aza-[4+3] and Aza-[3+2] Annulations for Synthesis of Dihydroazepines and Dihydropyrroles from Alkynes, Sulfonyl Azides, and 1,3-Dienes

      Sanghyuck Kim, Dr. Juntae Mo, Jaeeun Kim, Taekyu Ryu and Prof. Dr. Phil Ho Lee

      Article first published online: 16 JUN 2014 | DOI: 10.1002/ajoc.201402071

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      We have developed aza-[4+3] annulation via successive [3+2]-[2+1] cycloaddition-aza-Cope rearrangement for the synthesis of dihydroazepines. Aza-[3+2] annulation was accomplished via [3+2]-[2+1]-aza-Cope rearrangement-1,3-migration or [3+2]-[2+1]-Clock rearrangement to give dihydropyrroles along with molecular nitrogen. This procedure was applied to a one-pot process starting from terminal alkynes, azides, and dienes.

  10. Full Papers

    1. Synthetic Methods

      One-Pot Sequential Catalytic Hydration of Alkynes and α-Alkylation with Alcohols for the Synthesis of α-Alkylated Ketones

      Juan Ma, Nana Wang and Dr. Feng Li

      Article first published online: 12 JUN 2014 | DOI: 10.1002/ajoc.201402055

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      Ketone in one: A strategy for the synthesis of α-alkylated ketones via one-pot, sequential, catalytic hydration of alkynes and α-alkylation with alcohols was proposed and successfully accomplished. In the presence of [(IPr)AuCl]/AgOTf and [Cp*IrCl2]2/KOtBu, a variety of α-alkylated ketones were prepared in good to excellent yields. Cp*=η5-pentamethylcyclopentadienyl; IPr=1,3-bis(diisopropylphenyl)-imidazol-2-ylidene.

  11. Communications

    1. Computational Chemistry

      Using the Type II Cycloisomerization Reaction of 1,6-Enynes as a Mechanistic Probe to Identify the Real Catalytic Species of GaX3 and InX3

      Lian-Gang Zhuo, Yao-Cheng Shi and Prof. Dr. Zhi-Xiang Yu

      Article first published online: 6 JUN 2014 | DOI: 10.1002/ajoc.201402070

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      Get real: Type II cycloisomerization of 1,6-enynes generating nonconjugated dienes has been used as a mechanistic probe to study the real catalytic species for catalysts GaCl3, GaBr3, InBr3, and InI3. Experimental and computational results indicate that the real catalytic species are the positively charged species GaCl2+, GaBr2+, InBr2+, and InI2+, respectively.

  12. Full Papers

    1. Glycosylation

      Chemical Synthesis of the O-Antigen Repeating Unit of Escherichia coli O86 by an N-Formylmorpholine-Modulated One-Pot Glycosylation Strategy

      Dr. Arun B. Ingle, Dr. Chin-Sheng Chao, Wei-Cheng Hung and Prof. Kwok-Kong Tony Mong

      Article first published online: 6 JUN 2014 | DOI: 10.1002/ajoc.201402057

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      O, I say! An N-formylmorpholine (NFM)-modulated one-pot glycosylation was used for the synthesis for construction of 1,2-cis α-glycosidic linkages in the synthesis of the pentasaccharide repeating unit of the O-antigen that is found in Escherichia coli O86.

  13. Communications

    1. Supramolecular Gels

      Solvent-Modulated Self-Assembly of C3-Symmetric Tris-Urea into a Discrete Dimer and Supramolecular Gel

      Hideo Shimazu and Prof. Masamichi Yamanaka

      Article first published online: 4 JUN 2014 | DOI: 10.1002/ajoc.201402079

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      Self-made: C3-Symmetric tris-urea 1 self-assembles into either a discrete dimer or a supramolecular gel via continuous assembly, depending on the solvent used. In the less polar CDCl3 the discrete dimer was selectively formed, whereas in the more polar acetonitrile and acetone a supramolecular gel was obtained.

  14. Full Papers

    1. Solar Cells

      Monoanchoring (D-D-π-A) and Dianchoring (D-D-(π-A)2) Organic Dyes Featuring Triarylamine Donors Composed of Fluorene and Carbazole

      Abhishek Baheti, Dr. K. R. Justin Thomas, Ling-Chuan Lin and Dr. Kun-Mu Lee

      Article first published online: 2 JUN 2014 | DOI: 10.1002/ajoc.201402073

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      Less is more: Difluorenylamine-based dyes containing carbazole as an auxiliary donor, oligothiophene linkers, and cyanoacrylic acid acceptor/anchoring groups featuring two different architectures (D-D-π-A and D-D-(π-A)2) have been synthesized, characterized, and used in dye-sensitized solar cells (DSSCs). DSSCs based on the D-D-π-A-configured monoanchoring dyes are two to fivefold more efficient than those with the corresponding dianchoring congeners.

    2. Synthetic Methods

      Lewis-Base-Catalyzed Annulations of Nitroallylic Acetates as C3 Synthons with Electron-Deficient Alkenes

      Rongshun Chen, Xia Fan, Junyu Gong and Prof. Dr. Zhengjie He

      Article first published online: 27 MAY 2014 | DOI: 10.1002/ajoc.201402059

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      Allyl be back: 2-Nitroallylic acetates have been demonstrated as versatile C3 synthons in Lewis-base-catalyzed annulation reactions, which provides access to cyclopentenes and cyclohexenes with a nitro functionality. This work further broadens the scope of the Lewis-base-catalyzed annulation protocol for modified allylic derivatives. DMAP=4-dimethylaminopyridine.

  15. Communications

    1. Alkylation

      Copper(I)-Promoted Alkylation of Alkenylbenzyldimethylsilanes

      Prof. Dr. Takeshi Takeda, Ryo Matsumura, Hideki Wasa and Dr. Akira Tsubouchi

      Article first published online: 26 MAY 2014 | DOI: 10.1002/ajoc.201402060

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      An alkyl copper cross: Cross-coupling between alkenylbenzyldimethylsilanes and C(sp3)[BOND]X electrophiles, such as alkyl, allyl, and benzyl halides, proceeds in the presence of CuI-P(OEt)3 and Bu4NF(tBuOH)4 to produce di- and trisubstituted alkenes with complete retention of configuration. Bn=benzyl.

  16. Full Papers

    1. Porphyrins

      Combining the Diaza-Diels–Alder Reaction and Palladium-Catalyzed Aminations to Prepare Amino-Substituted Porphyrins

      Mean See Goh, Michael C. Pfrunder, John C. McMurtrie and Dennis P. Arnold

      Article first published online: 20 MAY 2014 | DOI: 10.1002/ajoc.201402049

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      Who’s the DADA? The diaza-Diels–Alder (DADA) reaction was combined with palladium-catalyzed amination of bromoporphyrins to generate aminated porphyrins. The X-ray crystal structure of an anthracene-derived aminoporphyrin nickel(II) complex confirms the sequence.

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