Asian Journal of Organic Chemistry

Cover image for Vol. 6 Issue 11

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

Editor: Theresa Kueckmann; Editorial Board Chairs: Sung Ho Kang, Keiji Maruoka, Jian Pei

Impact Factor: 2.788

ISI Journal Citation Reports © Ranking: 2016: 20/59 (Chemistry Organic)

Online ISSN: 2193-5815

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

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  1. Focus Reviews

    1. Polycyclic Aromatic Hydrocarbons

      Doping Polycyclic Aromatics with Boron for Superior Performance in Materials Science and Catalysis

      Esther von Grotthuss, Alexandra John, Thomas Kaese and Prof. Dr. Matthias Wagner

      Version of Record online: 24 NOV 2017 | DOI: 10.1002/ajoc.201700495

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      Delightful deficiency: Because of its vacant p orbital, an incorporated boron atom can imprint peculiar optoelectronic properties on polycyclic aromatic hydrocarbons (PAHs). Recently, synthetic strategies have been developed to provide access to B-PAHs that are specifically tailored to applications as catalysts for the activation of small molecules or as luminophores and charge carriers in optoelectronic devices.

  2. Full Papers

    1. Fluorescence

      Efficient Solution- and Solid-State Fluorescence for a Series of 7-Diethylaminocoumarin Amide Compounds

      Yatong Sun, Yunhui Sun, Dr. Songfang Zhao, Prof. Dr. Duxia Cao, Prof. Dr. Ruifang Guan, Prof. Dr. Zhiqiang Liu, Xueying Yu and Xun Zhao

      Version of Record online: 22 NOV 2017 | DOI: 10.1002/ajoc.201700555

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      7-Heaven: A series of 7-diethylaminocoumarin amides that exhibited strong fluorescence in THF, high-viscosity glycerol solution, and the solid state (powder) have been synthesized. The phenyl amide displayed enhanced fluorescence in the solid state relative to that in THF. The high-viscosity glycerol and solid states may restrict the rotation of the 7-diethylamino group, thereby leading to nonradiative deactivation and fluorescence enhancement.

  3. Communications

    1. Tandem Reactions

      Synthesis of Chiral Acyclic Pyrimidine Nucleosides with a Sulfur-Containing Side Chain via Enantioselective Tandem Conjugate Addition/Protonation

      Prof. Jian-Ping Li, Hao-Ran Tuo, Dr. Ming-Sheng Xie, Bo Kang, Prof. Gui-Rong Qu and Prof. Dr. Hai-Ming Guo

      Version of Record online: 22 NOV 2017 | DOI: 10.1002/ajoc.201700533

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      AdPro: A direct route to chiral pyrimidine acyclic nucleoside analogues with a sulfur-containing side chain has been reported via enantioselective tandem conjugated addition/protonation reactions of thioacetic acid to α-pyrimidine substituted acrylates. In the presence of a quinine-derived thiourea catalyst, diverse chiral sulfur-containing pyrimidine acyclic nucleoside analogues were formed in excellent yields (95–99 %) and moderate to excellent enantioselectivities (up to 99 % ee).

  4. Focus Reviews

    1. Michael Addition

      Recent Developments and Perspectives in the Zinc-Catalysed Michael Addition

      K. R. Rohit, S. M. Ujwaldev, K. Keerthi Krishnan and Prof. Dr. Gopinathan Anilkumar

      Version of Record online: 21 NOV 2017 | DOI: 10.1002/ajoc.201700491

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      Going greener: Zinc catalysis affords the Michael addition excellent reactivity and selectivity, and a broad substrate scope and mild reaction conditions have established this carbon–carbon and carbon–heteroatom bond-forming reaction as one of the most useful. This Focus Review examines what has been achieved since 2001 with the use of zinc, sometimes in conjunction with a ligand, in this important and increasingly green area of organic synthesis.

    2. Multicomponent Reactions

      1(3)-Formyl-β-carbolines: Potential Aldo-X Precursors for the Synthesis of β-Carboline-Based Molecular Architectures

      Nisha Devi, Sunit Kumar, Dr. Satyendra Kumar Pandey and Dr. Virender Singh

      Version of Record online: 20 NOV 2017 | DOI: 10.1002/ajoc.201700477

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      Generation X: The various methods for the diversity-oriented synthesis of β-carboline derivatives through an exploration of Kumujian C and its analogues are highlighted and summarized, which provide an excellent alternative to the classical Pictet–Spengler approach.

  5. Full Papers

    1. One-Pot Synthesis

      Pot-Economical Synthesis of Hydroxylated Arylethenyl-arylethynyl-arenes through Sequential Decarboxylative Perkin–Sonogashira Reactions

      Dr. Amit Shard, Dr. Rajesh Kumar, Danish Equbal and Dr. Arun Kumar Sinha

      Version of Record online: 17 NOV 2017 | DOI: 10.1002/ajoc.201700504

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      Harmonious tandem: A skeletally diverse chemical library of hydroxy-substituted arylethenyl-arylethynyl-arenes [C(sp2)−C(sp2) and C(sp2)−C(sp) framework] was prepared in good yields from terminal-alkyne-elaborated halogen-functionalized hydroxylated stilbenes. Their topological connectivity might afford them exceptional optoelectronic and medicinal properties. The products are amenable to downstream modification and can be further utilized for the synthesis of versatile molecular frameworks.

  6. Communications

    1. Tandem Reactions

      AgSbF6-Catalyzed Tandem Reaction of 2-Alkynylanilines with Cyclic Enynones: Efficient access to 3-Furo[3,2-c]chromenylindoles and Related Scaffolds

      Anuradha Dagar, Soumitra Guin and Dr. Sampak Samanta

      Version of Record online: 17 NOV 2017 | DOI: 10.1002/ajoc.201700511

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      Silver catalysis: A mild and efficient method has been developed for the direct synthesis of a series of 2-substituted-3-furo[2,3-c]chromenyl/tetrahydrobenzofuranyl indoles in good to high chemical yields by performing the tandem heterocyclization reaction between 2-alkynylanilines and 3-alkynyl-4H-chromen-4-ones/2-phenylethynylcyclohex-2-enone in the presence of 2.0 mol % of AgSbF6 as a Lewis acid catalyst.

    2. Rearrangement

      Benzyne-Promoted Curtius-Type Rearrangement of Acyl Hydrazides in the Presence of Nucleophiles

      Jing-Yu Guo, Chen-Hao Zhong, Zeng-Yang He and Prof. Dr. Shi-Kai Tian

      Version of Record online: 16 NOV 2017 | DOI: 10.1002/ajoc.201700598

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      Curtius-type rearrangement: A wide variety of N′-methyl-N′-phenyl acyl hydrazides were treated with oxygen, nitrogen, or sulfur nucleophiles in the presence of 2-(trimethylsilyl)phenyl triflate and CsF under mild conditions to afford structurally diverse carbamates or analogues. Importantly, complete retention of configuration was observed in the reaction of enantioenriched α-chiral alkanoyl hydrazides.

  7. Full Papers

    1. Charge Transfer Complexes

      Synthesis of Tetra(3-thienyl)biphenoquinone and its Charge Transfer Complex with Perylene

      Ryotaro Fujii, Dr.  Md. Awlad Hossain, Hisato Akimoto, Dr. Kazunori Hirabayashi, Prof. Dr. Toshio Shimizu, Dr. Kazuhiko Akiyama, Dr. Kenta Goto, Prof. Dr. Hiroyuki Nishikawa, Prof. Dr. Ken-ichi Yamashita and Prof. Dr. Ken-ichi Sugiura

      Version of Record online: 16 NOV 2017 | DOI: 10.1002/ajoc.201700560

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      Tetra(3-thienyl)biphenoquinone was designed and prepared. In contrast to reported aryl-substituted biphenoquinones, the title compound takes a nearly planar structure. This resulted in good conjugation in the entire molecule and the formation of a charge transfer complex with perylene in the solid state.

    2. Metal–Organic Frameworks

      A CuII-based Metal–Organic Framework as an Efficient Photocatalyst for Direct Hydroxylation of Benzene to Phenol in Aqueous Solution

      Li Zhang, Shuhai Qiu, Prof. Guoqing Jiang, Prof. Guomin Jiang and Prof. Ruiren Tang

      Version of Record online: 15 NOV 2017 | DOI: 10.1002/ajoc.201700501

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      MOFs for hydroxylation catalysis: A type of CuII-based metal–organic framework (MOF) has been prepared and characterized, which shows an excellent performance in the direct hydroxylation of benzene to phenol in aqueous solution.

  8. Communications

    1. Olefin Functionalization

      Manganese-Dioxide-Catalyzed Trifluoromethylation and Azidation of Styrenyl Olefins via Radical Intermediates

      Prabhakar Panday, Parul Garg and Dr. Anand Singh

      Version of Record online: 14 NOV 2017 | DOI: 10.1002/ajoc.201700508

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      Versatile radicals: MnO2-catalyzed trifluoromethylation and azidation reactions of styrenes and enol acetates are described. The reactions used air/oxygen as the oxidant under mild conditions, with the Langlois reagent and trimethylsilyl azide as precursors for the trifluoromethyl and azide radicals, respectively. The radical species were intercepted by styrenes and enol acetates to afford trifluoromethylated alcohols/ketones and ketoazides, respectively.

    2. Alkoxylation

      Palladium-Catalyzed ortho-Alkoxylation of Tertiary Benzamides: H2SO4 as an Effective Additive

      Fang-Cheng Qiu, Qi Xie and Prof. Dr. Bing-Tao Guan

      Version of Record online: 14 NOV 2017 | DOI: 10.1002/ajoc.201700525

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      H2SO4 as an effective additive: A direct synthesis of aryl ethers has been developed via a palladium-catalyzed alkoxylation of tertiary benzamides with alcohols. H2SO4 was found to be a key additive, which could greatly enhance the catalytic reactivity of the palladium catalyst.

    3. Hydroboration

      Copper-Catalyzed Enantioselective Hydroboration of 1,1-Disubstituted Alkenes: Method Development, Applications and Mechanistic Studies

      Lu Wen, Fengchang Cheng, Han Li, Shuoqing Zhang, Prof. Dr. Xin Hong and Prof. Dr. Fanke Meng

      Version of Record online: 13 NOV 2017 | DOI: 10.1002/ajoc.201700503

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      Copper statues: Copper-catalyzed enantioselective formation of tertiary alkyl-copper complexes followed by protonation affords hydroboration products in high yields and with excellent enantioselectivity.

  9. Full Papers

    1. Synthetic Methods

      Selective S-Deacetylation of Functionalized Thioacetates Catalyzed by Dy(OTf)3

      Jiun-Rung Guo, Hsin-Yi Huang, Yi-Ling Yan and Prof. Chien-Fu Liang

      Version of Record online: 9 NOV 2017 | DOI: 10.1002/ajoc.201700481

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      Dy another day: A Dy(OTf)3-catalyzed S-deacetylation of functionalized thioesters has been developed. Moreover, selective S-deacetylation can be achieved by combining Dy(OTf)3 with NaHCO3. Furthermore, glycosyl 1-thioacetate has been successfully transformed into glycosyl 1-thiol by using Dy(OTf)3 in a co-solvent system.

  10. Communications

    1. Carboxylation | Very Important Paper

      Copper-Catalyzed Carboxylation of Aryl- and Alkenyltrialkoxysilanes

      Thanh V. Q. Nguyen, Dr. Woo-Jin Yoo and Prof. Dr. Shū Kobayashi

      Version of Record online: 8 NOV 2017 | DOI: 10.1002/ajoc.201700519

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      Carbonated drinks: Aryl- and alkenylalkoxysilanes undergo carboxylation with carbon dioxide in the presence of CuBr as a catalyst and CsF as an activator, to afford carboxylic acids in good to high yields.

  11. Full Papers

    1. Semiconductors

      Development of Pyrene Derivatives as Promising n-Type Semiconductors: Synthesis, Structural and Spectral Properties

      Minglun Liu, Xiaojie Gong, Chaoyue Zheng and Prof. Deqing Gao

      Version of Record online: 8 NOV 2017 | DOI: 10.1002/ajoc.201700441

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      Just my type: A series of pyrene derivatives were synthesized. In contrast with 1,6-position substitution, 1,8-position substitution had smaller dihedral angles and facilitated large conjugation and intermolecular stacking. The dicyanovinylene substitution strengthened the coplanarity and enhanced π-conjugated systems. The lowest unoccupied molecular orbital (LUMO) energy level was located deeply and they may be promising candidates of n-type semiconductors.

    2. Synthesis of Esters

      Chemoselective Oxidative Esterification and Iodocyclization of Hydroxyalkynyl Aldehydes

      Shiv Kumar, Monika Patel, Dr. Rakesh K. Saunthwal and Prof. Akhilesh K. Verma

      Version of Record online: 8 NOV 2017 | DOI: 10.1002/ajoc.201700375

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      Part of the solution: In different solvents, iodine chemoselectively participates in the oxidative esterification or the electrophilic iodocyclization of hydroxyalkynyl aldehydes that contain a primary alcohol moiety. This protocol provides alkyl 4-(3-hydroxyalkynyl)benzoates when performed in an alcohol. In CH2Cl2, the aldehydes undergo an electrophilic iodocyclization to afford products that contain a bioactive dihydrofuran/pyran ring system.

  12. Communications

    1. Synthetic Methods

      Temperature-Controlled Base-Promoted Cyclization for the Synthesis of 2-Amino-4H-benzo[d][1,3]thiazin-4-ones and 2-Thioxo-4(3H)-quinazolinones

      Zhi-Wen Zhou, Feng-Cheng Jia, Cheng Xu, Shi-Fen Jiang, Prof. Yan-Dong Wu and Prof. An-Xin Wu

      Version of Record online: 7 NOV 2017 | DOI: 10.1002/ajoc.201700443

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      Kinetic control: A synergetic Na2CO3/TBHP-promoted tandem oxidation/decarboxylative cyclization of isothiocyanates and isatins has been developed (see scheme; TBHP=tert-butyl hydroperoxide). This chemoselective reaction enables the fast construction of both 4H-benzo[d][1,3]thiazin-4-ones and 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones in moderate to high yields. In addition, this method features commercially available substrates, easy operation, and mild conditions.

  13. Full Papers

    1. Polycyclic Aromatic Hydrocarbons

      Palladium-Catalyzed Double Suzuki Reactions: Synthesis of Dibenzo[4,5:6,7]cyclohepta[1,2,3-de]naphthalenes

      Dr. Xin Li, Prof. Dr. Jian-Wei Han, Yan-Xia Zhang and Prof. Dr. Henry N. C. Wong

      Version of Record online: 3 NOV 2017 | DOI: 10.1002/ajoc.201700484

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      Bicyclic molecules: The first synthesis of dibenzo[4,5:6,7]cyclohepta-[1,2,3-de]naphthalene (DBnaphthalene) and its derivatives using palladium-catalyzed double Suzuki coupling reactions is reported. These DBnaphthalenes are expected to be employed in the “bottom-up” synthesis of functional aromatic molecules.

  14. Communications

    1. Heterogeneous Catalysts

      Zirconia-Supported Cu(I)-Stabilized Copper Oxide Mesoporous Catalyst for the Synthesis of Quinazolinones Under Ambient Conditions

      L. Parashuram, Dr. Swamy Sreenivasa, S. Akshatha, Dr. V. Udaya Kumar and Dr. Sandeep Kumar

      Version of Record online: 3 NOV 2017 | DOI: 10.1002/ajoc.201700467

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      Quinazolinones: A simple protocol for the catalytic synthesis of quinazolines in the presence of a cost-effective and reusable mesoporous ZrO2-supported Cu2O (Cu2ZrO3) catalyst is described. The present protocol showed good tolerance for various substituted aldehydes and good yields for quinazolinone derivatives.

    2. Synthetic Methods

      Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C

      Dr. Takayuki Kudoh, Yuya Araki, Natsumi Miyoshi, Mizuho Tanioka and Prof. Dr. Akira Sakakura

      Version of Record online: 3 NOV 2017 | DOI: 10.1002/ajoc.201700568

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      Henry reaction of chiral secondary nitroalkanes constructed nitrogen-containing tetrasubstited carbon stereocenters with high diastereoselectivity. Protecting groups of the nitroalkanes played a key role to control the diastereoselectivity. Using the Henry adducts as key intermediates, a total synthesis of manzacidins A and C has been achieved.

  15. Full Papers

    1. Ionic Liquids

      Towards a Step-Economical and Waste-Free [hmim]Br-Catalyzed Deprotection of β-Sulfido Carbonyl Groups into (E)-Enones and Mechanistic Insights

      Dr. Yogesh Thopate, Richa Singh, Tanuj Sharma, Dr. Mohammad I. Siddiqi and Dr. Arun K. Sinha

      Version of Record online: 2 NOV 2017 | DOI: 10.1002/ajoc.201700409

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      Waste not, want not: The direct deprotection of β-sulfido compounds into α,β-unsaturated alkenes has been achieved by using a neutral ionic liquid, [hmim]Br, as a solvent and catalyst. This method is mild, highly regioselective, and offers broad substrate scope and high yields, as well as recyclability of the ionic liquid for up to five cycles. 1H NMR and MS (DART) analysis provided mechanistic insight into the role of [hmim]Br in the reaction.

    2. Density Functional Calculations

      Mechanistic Investigation into RhIII-Catalyzed Intramolecular Redox-Neutral Annulation of Aryl Hydrazines with a Tethered Alkyne

      Weirong Wu, Dongcheng Ren, Benzhen Xu, Xiaoying Ma, Caiyun Huang, Jing Zhang and Tao Liu

      Version of Record online: 2 NOV 2017 | DOI: 10.1002/ajoc.201700469

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      All in the details: DFT calculations for the Cp*RhIII-catalyzed (Cp*=η5-pentamethylcyclopentadienyl) intramolecular redox-neutral annulation of aryl hydrazines that contain tethered alkynes were performed to understand the detailed reaction mechanism for the regioselective synthesis of 2-amidealkyl indoles by C−H activation.

    3. Synthetic Methods

      Molecular Iodine-Promoted Transimination for the Synthesis of 6-Phenylpyrido[2′,1′:2,3]imidazo[4,5-c]quinoline and 6-(Pyridin-2-yl)pyrido[2′,1′:2,3]imidazo[4,5-c]quinolines

      Satish Sunkari, Dr. Siddiq Pasha Shaik, Namballa Hari Krishna, Dr. Ayanampudi Venkata Subba Rao, Bheeshma Geetanjali Kodiripaka, Dr. Abdullah Alarifi and Dr. Ahmed Kamal

      Version of Record online: 25 OCT 2017 | DOI: 10.1002/ajoc.201700357

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      I-2 can-do system: An efficient I2-mediated approach for the synthesis of 6-phenylpyrido[2′,1′:2,3]imidazo[4,5-c]quinoline heterocyclic skeletons has been achieved from the reaction of benzylamines and 2-(imidazo[1,2-a]pyridin-2-yl)anilines. This one-pot protocol proceeds through an oxidation/transimination/cyclization/aromatization reaction sequence under metal-free conditions to result in the formation of N−C and C−C bonds.

  16. Communications

    1. Polycyclic Aromatic Hydrocarbons

      Unexpected One-Pot Synthesis of Diindolotriazatruxene: A Planar Electron-Rich Scaffold Toward Highly π-Extended PAHs

      Xiangchun Li, Chunyu Wang, Yibo Xue, Cheng Meng, Prof. Wen-Yong Lai and Prof. Wei Huang

      Version of Record online: 24 OCT 2017 | DOI: 10.1002/ajoc.201700498

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      Extended PIe: A unique planar, highly π-extended and electron-rich skeleton, 4Br-DIT was synthesized by a facile one-pot strategy. A combination of thermal, optical, and electrochemical investigations has shown the promise of the resulting diindolotriazatruxene unit as a building block to construct highly π-extended polycyclic aromatic hydrocarbons (PAHs).

    2. Lignin Chemistry

      Oxidative Coupling of â-O-4′ Dilignol Models Leading to Polycyclic Products with Rare Interlignol Linkages

      Chang Peng, Prof. Wujun Liu, Siyang Ning, Prof. Guangbo Ge and Prof. Zongbao K. Zhao

      Version of Record online: 24 OCT 2017 | DOI: 10.1002/ajoc.201700529

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      Polycycles containing rare interlignol linkages were obtained from β-O-4′ type dilignols via oxidative coupling reactions. Oxidative coupling of these dilignols with hypervalent iodine(III) reagents led to two series of highly fused polycyclic products, dibenzo[b,d]oxepine and 2,7-dioxabicyclo[3,3,1]nonane derivatives.

    3. Cyclopropanation

      Pd-Catalyzed Cyclopropanation Reaction of Aliphatic Ketones with Monosubstituted Allyl Reagents

      Jian-Qiang Huang, Jing-Feng Zhao, Zhen Yang, Chang-Hua Ding, Prof. Dr. Xue-Long Hou, Prof. Dr. Xiao-Shui Peng and Prof. Dr. Henry Nai Ching Wong

      Version of Record online: 24 OCT 2017 | DOI: 10.1002/ajoc.201700541

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      Selected cyclopropanes: A Pd-catalyzed cyclopropanation reaction with aliphatic ketones as nucleophiles using a modified pyridine-NHC ligand was achieved. The reaction afforded the corresponding cyclopropanes in moderate to good yields with high cyclopropane/allylation selectivity.

  17. Full Papers

    1. Carboranes

      Solid-State Thermochromic Luminescence through Twisted Intramolecular Charge Transfer and Excimer Formation of a Carborane−Pyrene Dyad with an Ethynyl Spacer

      Dr. Kenta Nishino, Hideki Yamamoto, Dr. Kazuo Tanaka and Prof. Yoshiki Chujo

      Version of Record online: 23 OCT 2017 | DOI: 10.1002/ajoc.201700390

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      Spacer, the final frontier: The pyrene-tethered carborane CBEP exhibited orange emission at room temperature, which was caused by intramolecular charge transfer in the solid state, and green excimer emission at 77 K. The steric influence of an ethynyl spacer group allowed the o-carborane to suppress aggregation-caused quenching without the inhibition of excimer formation.

    2. Heterocyclic Chemistry

      Synthesis of Indolizine-Containing Diaryl- and Triarylmethanes through a Cu-Catalyzed Domino Cyclization of 2-(2-Enynyl)pyridines

      Sriram Mahesh, Dr. Dilip K. Paluru, Feroz Ahmad, Swati Patil, Guddi Kant and Dr. Ramasamy Vijaya Anand

      Version of Record online: 20 OCT 2017 | DOI: 10.1002/ajoc.201700419

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      Need a bicycle? An effective method for the synthesis of indolizine-containing unsymmetrical diaryl- and triarylmethane derivatives through a Cu-catalyzed domino cyclization of 2-(2-enynyl)pyridines is described.

  18. Communications

    1. Synthetic Methods

      Synthesis and Characterization of Hybrid Mg(OH)2 and CeCO3OH Composite with Improved Activity Towards Henry Reaction

      Ravi Tomar, Nidhi Singh, Garima Rathee, Neeraj Kumar, Dr. Vartika Tomar and Prof. Dr. Ramesh Chandra

      Version of Record online: 20 OCT 2017 | DOI: 10.1002/ajoc.201700485

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      A new approach was developed for carbon–carbon bond formation via Henry reaction using a mixture of Mg(OH)2 and CeCO3OH (MgCe-HDC). The effects of temperature, solvent, and the amount of catalyst were investigated to find the optimum reaction conditions. The highest yield of the nitroaldol product, 92 %, was achieved over the reusable solid base catalyst in solvent-free conditions at 20 °C.

    2. Fluoroalkylation

      Ru(bpy)3Cl2 as a Photocatalyst for Visible-Light-Induced Fluoroalkylation of Anilines with BrCF2CF2Br: A Facile Route to 2-Bromo-1,1,2,2-tetrafluoroethyl Arenes

      Jingjing Kong, Dr. Jianfang Jiang, Yang Huang, Yue-Guang Lou, Dr. Xiao-Fei Li and Dr. Chun-Yang He

      Version of Record online: 19 OCT 2017 | DOI: 10.1002/ajoc.201700422

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      Readily available: A convenient method for the preparation of 2-bromo-1,1,2,2-tetrafluoroethyl arenes, using commercially available anilines and BrCF2CF2Br as starting materials is described. The reaction is highly efficient and proceeds under the blue-LED irradiation, enabling the installation of amino and fluoroalkyl moieties.

    3. Electrophilic Aromatic Substitution

      Ipso Nitration of 2-Halothiophenes with Silver Nitrate

      Gon-Ann Lee, Hung-Chun Lin, Hsin-Yi Lee, Chien-Hsun Chen and Hsiang-Yun Huang

      Version of Record online: 18 OCT 2017 | DOI: 10.1002/ajoc.201700392

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      Ipsodelic: A simple method for the ipso nitration of a series of aryl substituted 2-halothiophenes to give 2-nitrothiophenes is described. The reaction uses AgNO3, a readily available reagent, as the nitration reagent and no additives are needed for the transformation.

  19. Full Papers

    1. Sulfonamidation

      RuII-Catalyzed ortho-Sulfonamidation of α-Tetralones with Sulfonyl Azides and Synthesis of Sivelestat by Aromatic C−H Activation

      Medikonda V. Krishna Rao, Keesari Nagarjuna Reddy, Dr. Balasubramaniam Sridhar and Dr. Basi V. Subba Reddy

      Version of Record online: 18 OCT 2017 | DOI: 10.1002/ajoc.201700356

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      Amide other reactions: A method has been developed for the sulfonamidation of α-tetralones and 1,4-naphthoquinones by using sulfonyl azides and a RuII/AgI catalytic system (see scheme; DCE=1,2-dichloroethane). Tetralones underwent C−H bond functionalization exclusively at the ortho position, whereas 1,4-addition was the primary reaction for 1,4-naphthoquinone. This highly regioselective approach was also used to synthesize sivelestat, an inhibitor of human neutrophil elastase.

  20. Communications

    1. Alkylation

      Brønsted-Acid-Catalyzed Substrate-Controlled and Site-Selective Friedel–Crafts Alkylation: A New Strategy for Post-Modification of 1,2-Dihydroquinolines

      Jin Huang, Prof. Guangxun Li, Guobin Yang, Prof. Jinzhong Zhao and Prof. Zhuo Tang

      Version of Record online: 18 OCT 2017 | DOI: 10.1002/ajoc.201700438

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      Post-modifications of simple 1,2-dihidroquinolines (1,2-DHQs) through regioselective Friedel–Crafts alkylations were achieved using simple Brønsted acid catalysts. Suitable substrates allowed modifications of the specific sites.

    2. Thioamide Synthesis

      Elemental-Sulfur-Promoted C(sp3)−H Activation of Methyl Heteroarenes Leading to Thioamides

      Dr. Jianming Liu, Shanshan Zhao, Dr. Xuyang Yan, Yanyan Zhang, Shufang Zhao, Kelei Zhuo and Dr. Yuanyuan Yue

      Version of Record online: 18 OCT 2017 | DOI: 10.1002/ajoc.201700532

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      Release Me2N(ight)! Sulfur-promoted C(sp3)−H activation of methyl heteroarenes generates bioactive thioamides. This transformation successfully furnished a series of heterocyclic thioamides with excellent yields and it could be conducted on gram scale with good reaction efficiency. Mechanistic studies showed that methyl heteroarenes reacted with dimethylamine released from DMF to form the desired thioamide.

  21. Full Papers

    1. Lanthanide Complexes

      One-Step Reaction for Screening of Chromophores to Improve the Luminescence of Lanthanide Complexes

      Dr. Lixiong Dai, Dr. Wai-Sum Lo, Junhui Zhang and Dr. Ga-Lai Law

      Version of Record online: 18 OCT 2017 | DOI: 10.1002/ajoc.201700403

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      Less screen time: A stable lanthanide template was prepared by a one-step coupling reaction as a fast-screening tool to select suitable chromophores for sensitizing EuIII luminescence. Screening took place with Sonogashira or Suzuki reactions, and the photophysical properties of these complexes and their potential suitability for biological applications has been assessed

    2. Peptides

      Isolation and Structure Determination of New Antibacterial Peptide Curacomycin Based on Genome Mining

      Issara Kaweewan, Dr. Hisayuki Komaki, Dr. Hikaru Hemmi and Dr. Shinya Kodani

      Version of Record online: 17 OCT 2017 | DOI: 10.1002/ajoc.201700433

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      Sweet Child O′ Mining: A new antibacterial cyclic peptide, named curacomycin, and its analogue dechlorocuracomycin were isolated based on genome mining. The biosynthetic pathways for these peptides were proposed by analysis of biosynthetic gene clusters that were found in the genome sequences.

    3. Reaction Kinetics

      A Convenient Method for the Direct Acquisition of Kinetic Rate Data for Catalytic Organic Reactions by Gas Uptake Measurements

      Yu-Jie Wang, Wei-Tang Li and Prof. Lei Jiao

      Version of Record online: 16 OCT 2017 | DOI: 10.1002/ajoc.201700406

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      The new going rate: A convenient method enabling direct acquisition of kinetic rate data for organic reactions involving gas uptake is reported. By measuring isobaric mass flow, the real-time rate can be directly obtained to construct a high-quality full-course rate profile of a reaction. The method is suitable for studying both the initial rate and the kinetics of reaction progress, facilitating studies on the kinetics and mechanisms of many organic reactions involving gas uptake.

    4. Synthetic Methods

      Synthesis of Indenes that are Derived from Aldimines with Enones Under Rhodium(III) Catalysis

      Sang Hoon Han, Saegun Kim, Dr. Neeraj Kumar Mishra, Hyunjung Oh, Myung Hoon Choi, Dong Seok Choi, Hyeon Ju Lim, Dong Yeop Shin and Prof. Dr. In Su Kim

      Version of Record online: 16 OCT 2017 | DOI: 10.1002/ajoc.201700473

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      The IIIs have it: The rhodium(III)-catalyzed C−H alkylation and intramolecular cyclization of aldimines with enones provides direct access to C2-carbonyl-substituted indenes with excellent site selectivity and functional-group compatibility.

    5. C(sp3)−H Bond Functionalization

      CuI/I2-Mediated Intramolecular Oxidative Cyclization Reaction of N-(2-pyridyl)amidines by the Direct Double C−H Functionalization of a C(sp3)−H Bond

      Prof. Dr. Fengping Yi, Songxing Zhang, Prof. Dr. Lirong Zhang, Dr. Weiyin Yi and Rui Yu

      Version of Record online: 12 OCT 2017 | DOI: 10.1002/ajoc.201700442

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      New imidazo[1,2-a]-pyridines bearing one hydroxyl group, the structures of which are completely different from previous reported ones, were synthesized by double C(sp3)−H bond functionalization at the same carbon atom.

  22. Communications

    1. NHC Catalysis

      N-Heterocyclic-Carbene-Catalyzed Redox Lactonization of o-Hydroxycinnamaldehydes and o-Hydroxycinnamyl Alcohols to Coumarins

      Dr. Jingjing Meng, Qiang Jiang, Xinyang Li, Li Wan, Prof. Zheng Fang and Prof. Kai Guo

      Version of Record online: 12 OCT 2017 | DOI: 10.1002/ajoc.201700458

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      As quick as it gets: An N-heterocyclic-carbene (NHC)-catalyzed lactonization of o-hydroxycinnamaldehydes and o-hydroxycinnamyl alcohols afforded coumarins with distinct chemoselectivity in 30–98 % yields after 0.5 h.

    2. Arylation Reactions | Very Important Paper

      Arylation of Aniline C(sp3)−H Bonds with Phenols via an In Situ Activation Strategy

      Dr. Yong-Yuan Gui, Zi-Xiao Wang, Prof. Dr. Wen-Jun Zhou, Li-Li Liao, Lei Song, Zhu-Bao Yin, Dr. Jing Li and Prof. Dr. Da-Gang Yu

      Version of Record online: 10 OCT 2017 | DOI: 10.1002/ajoc.201700450

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      A general and efficient arylation of aniline C(sp3)−H bonds with phenols has been achieved by an in situ activation strategy via visible-light photoredox/nickel dual catalysis. This protocol directly uses phenols as proelectrophiles and features high step-efficiency, time-economy, environmental impact, broad substrate scope, high yields, good functional-group tolerance, and low catalyst loading.

  23. Full Papers

    1. Cross-Coupling

      Nickel-Catalyzed C−N Cross-Coupling of Primary Imines with Subsequent In Situ [2+2] Cycloaddition or Alkylation

      Dennis J. Power, Kieran D. Jones, Dr. Sven S. Kampmann, Dr. Gavin R. Flematti and Dr. Scott G. Stewart

      Version of Record online: 9 OCT 2017 | DOI: 10.1002/ajoc.201700464

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      Knights who say Ni: A new method for the C−N cross-coupling of aryl chlorides with primary imines by using an air-stable nickel(0) catalyst is reported. This process can be readily coupled with a Staudinger reaction or an alkylation step.

    2. Allenylation

      Theoretical Studies of Allene Synthesis through Cadmium Iodide-Mediated Allenylation of Terminal Alkynes

      Yulin Han and Dr. Xue Zhang

      Version of Record online: 9 OCT 2017 | DOI: 10.1002/ajoc.201700389

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      Allene abduction: We investigated the mechanism of the CdI2-mediated reaction of an amine and two molecules of terminal alkynes for the synthesis of allenes by using DFT calculations. The results reveal that the pyrrolidine serves not only as a reactant but also as a shuttle in a proton relay.

  24. Communications

    1. Cross-Dehydrogenative Coupling

      Synthesis of Pyrazine–Thiazole Biheteroaryl Compounds through Base-Promoted Oxidative Cross-Dehydrogenative Coupling Reactions

      Yuanyuan Shan, Dr. Miao Lai, Dr. Rui Li, Dr. Zhiyong Wu and Prof. Dr. Mingqin Zhao

      Version of Record online: 6 OCT 2017 | DOI: 10.1002/ajoc.201700449

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      An efficient one-pot protocol for the oxidative cross-dehydrogenative coupling reaction of pyrazine N-oxides and 1,3-azole derivatives has been disclosed. Various biheteroaryl compounds were obtained in moderate to good yields. This methodology provides a practical pathway for the construction of pyrazine–thiazole biheteroaryl moieties and features high practicality and environmental friendliness.

  25. Full Papers

    1. Disaccharides

      Design of Disaccharide Modules for a Programmable One-Pot Synthesis of Building Blocks with LacNAc Repeating Units for Asymmetric N-Glycans

      Cheng-Yueh Ting, Yu-Wei Lin, Prof. Chung-Yi Wu and Prof. Chi-Huey Wong

      Version of Record online: 14 SEP 2017 | DOI: 10.1002/ajoc.201700393

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      Programming is fun! A strategy for the assembly of N-glycans with LacNAc repeats has been developed by a combination of programmable one-pot synthesis and enzymatic approach. The strategy was started with a programmable one-pot synthesis of LacNAc repeats followed by deprotection and enzymatic glycosylation using galactosyl transferase and sialyltransferase sequentially.

  26. Communications

    1. Domino Reactions

      Direct Functionalization of Azepane via Azomethine Ylides: A Highly Efficient Synthesis of Spirooxindoles Bearing a 1-Azabicyclo[5.3.0]decane Moiety

      Prof. Xiangtai Meng, Yanlong Du, Qi Zhang, Aimin Yu, Youquan Zhang, Jiru Jia and Prof. Xiujie Liu

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/ajoc.201700384

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      Ylides with a twist: Spirooxindoles bearing a 1-azabicyclo[5.3.0]decane moiety were synthesized in one step via direct functionalization of the azepane without a transition metal or oxidants. This is an efficient process for the synthesis of fused 7/5-heterobicyclic systems in one step. Furthermore, cycloaddition of the in-situ-generated azomethine ylide only proceeded for alkenyl sulfone dipolarophiles.

  27. Full Papers

    1. Green Catalysis

      Activated Neutral Alumina as a Simple and Reusable Catalyst for the Synthesis of N,N-Bis[(alkyl/arylthio)methyl]amines: A Solid-Supported Protocol Under Solvent-Free Conditions

      Animesh Mondal and Prof. Chhanda Mukhopadhyay

      Version of Record online: 7 SEP 2017 | DOI: 10.1002/ajoc.201700386

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      Going forward in neutral: A new strategy is described for the solid-supported synthesis of N,N-bis[(alkylthio)methyl]amine and N,N-bis[(arylthio)methyl]amine derivatives, catalyzed by activated neutral Al2O3 (calcined at 600 °C) under solvent-free stirring conditions at room temperature (25–30 °C).

  28. Communications

    1. Oxazoline Synthesis | Very Important Paper

      Nickel-Catalyzed C−H Heteroarylation of Chiral Oxazolines

      Peng Lu, Chong-Lei Ji and Dr. Zhan Lu

      Version of Record online: 6 SEP 2017 | DOI: 10.1002/ajoc.201700446

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      It only costs a nickel! A nickel-catalyzed C−H heteroarylation at the 2 position of oxazolines with heteroaryl halides is described. This method is an efficient synthesis for various oxazoline-containing multidentate chiral ligands.

  29. Focus Reviews

    1. Click Chemistry

      Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

      Dr. Maulidan Firdaus

      Version of Record online: 29 AUG 2017 | DOI: 10.1002/ajoc.201700387

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      Clicking terpenes: This Focus Review covers the development of thiol–ene (click) chemistry for the preparation of platform chemicals, monomers, and polymers derived from terpenes. The use of this reaction has led to various advanced applications.

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