The Chemical Record

Cover image for Vol. 17 Issue 6

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

Editor-in-Chief: Hisashi Yamamoto, Managing Editor: Brian Johnson

Impact Factor: 3.855

ISI Journal Citation Reports © Ranking: 2016: 45/166 (Chemistry Multidisciplinary)

Online ISSN: 1528-0691

Associated Title(s): Angewandte Chemie International Edition, Chemistry - A European Journal, Chemistry – An Asian Journal, Chinese Journal of Chemistry, Israel Journal of Chemistry, Journal of the Chinese Chemical Society

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  1. Personal Accounts

    1. Development of Proton-Responsive Catalysts

      Lin Wang, Ryoichi Kanega, Hajime Kawanami and Yuichiro Himeda

      Version of Record online: 26 JUN 2017 | DOI: 10.1002/tcr.201700023

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      In this account, we describe a successful strategy for a novel catalyst design and modification, which is based on an acid-base equilibrium between hydroxy group and oxyanion group on the ligands. In particular, the oxyanion group generated from the phenolic hydroxy group plays significant roles not only in catalytic activity and water solubility but also in the tuning of the catalytic performances during the course of the reaction.

    2. Tautomerization and Dissociation of Molecular Peptide Radical Cations

      Xiaoyan Mu, Tao Song, Chi-Kit Siu and Ivan K. Chu

      Version of Record online: 26 JUN 2017 | DOI: 10.1002/tcr.201700013

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      Gas phase molecular peptide radical cations [PEPTIDE]•+ exhibit rich chemistry of radical/charge migrations, resulting in a variety of radical tautomers. Their subsequent dissociations through specific radical-induced bond cleavages can generate a large array of fragment ions, giving invaluable sequence information for mass spectrometry–based protein identification.

    3. In-Situ Generated and Premade 1-Copper(I) Alkynes in Cycloadditions

      Prof. Xinyan Wang, Xingyong Wang, Xuesong Wang, Jianlan Zhang, Chulong Liu and Prof. Dr. Yuefei Hu

      Version of Record online: 22 JUN 2017 | DOI: 10.1002/tcr.201700011

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      Based on the investigation of the references and our works on CuAAC reaction, we found the difference and conversion between the in-situ generated and the premade 1-copper(I) alkynes. Finally, the novel carboxylic acid-promoted CuAAC strategy was developed, which has been proven to be the most convenient and highly efficient CuAAC method to date. Furthermore, the novel function of the premade 1-copper(I) alkynes as excellent dipolarophiles was first disclosed and applied. In this article, a series of works reported by our group for the in-situ generated and the premade 1-copper(I) alkynes in cycloadditions are reviewed.

    4. Precisely tailored DNA Nanostructures and their Theranostic Applications

      Bing Zhu, Lihua Wang, Jiang Li and Chunhai Fan

      Version of Record online: 13 JUN 2017 | DOI: 10.1002/tcr.201700019

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      DNA nanostructures with precisely tailorable structural parameters bring superior physical and chemical properties like controlled valences, anisotropy, and further lead to powerful functions in theranostic applications including ultrasensitive biosensing, cellular imaging, and intelligent drug delivery.

    5. Manganese-Mediated Homolytic Aromatic Substitution With Phosphinylidenes

      Dr. Olivier Berger and Prof. Jean-Luc Montchamp

      Version of Record online: 12 JUN 2017 | DOI: 10.1002/tcr.201700021

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      Carbon-phosphorus (C−P) bond-forming reactions via homolytic aromatic substitution (HAS) of non-functionalized substrates with phosphinylidene P(O)H compounds are becoming a useful synthetic tool for the preparation of aryl and heteroaryl phosphonates, phosphinates, and phosphine oxides. This review specifically covers recent work using manganese-mediated free radical processes.

    6. Conformational Dynamics of mRNA in Gene Expression as New Pharmaceutical Target

      Tamaki Endoh and Naoki Sugimoto

      Version of Record online: 17 MAY 2017 | DOI: 10.1002/tcr.201700016

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      Recent functional studies demonstrate the importance of mRNA conformational dynamics in the regulation of gene expression and protein function. The structure, stability, and kinetic properties of nucleic acids are sensitive to the intracellular molecular environment, such as the concentrations of molecular crowding agents and molecules that interact with mRNA. Here, we review the roles of mRNA conformational dynamics in consecutive and concurrent processes involved in gene expression and discuss the possibility of using nucleic acid conformational dynamics as a basis of pharmaceutical drug development.

    7. Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels−Alder Reactions

      Dr. Mingsheng Xie, Dr. Lili Lin and Prof. Dr. Xiaoming Feng

      Version of Record online: 16 MAY 2017 | DOI: 10.1002/tcr.201700006

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      In this review, the recent developments in catalytic asymmetric inverse-electron-demand hetero-Diels−Alder reaction, which is recognized as one of the most powerful routes to construct highly functionalized and enantioenriched six-membered heterocycles, are described. The article is organized on the basis of different kinds of electron-deficient heterodienes, including α,β-unsaturated ketones/aldehydes, o-benzoquinones, α,β-unsaturated imines, N-aryl imines, o-benzoqinone imides, and other aza-olefins.

    8. Cascades of Interrupted Pummerer Reaction-Sigmatropic Rearrangement

      Prof. Dr. Hideki Yorimitsu

      Version of Record online: 10 MAY 2017 | DOI: 10.1002/tcr.201700017

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      New Pummerer technology has been devised, consisting of a beautiful cascade of an interrupted Pummerer reaction of unsaturated sulfoxide and the subsequent charge-accelerated [3,3] sigmatropic rearrangement. The reactions are uniquely useful for the synthesis of heteroaromatic compounds and biaryls because they are efficient, robust, redox-neutral, regioselective, and metal-free, which perfectly fits the need of modern organic synthesis.

    9. Physicochemical Nature of Perfluoroalkyl Compounds Induced by Fluorine

      Prof. Takeshi Hasegawa

      Version of Record online: 9 MAY 2017 | DOI: 10.1002/tcr.201700018

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      Perfluoroalkyl (Rf) compounds exhibit unique bulk properties, which cannot be explained by an extended or corrected concept of normal alkyl compounds depending on the dispersion force. The helical conformation of an Rf group induces two-dimensional tight molecular aggregation generated cooperatively with the dipole-dipole interaction, which results in invisible dipoles in a bulk scale accounting for the Rf-specific properties comprehensively.

    10. Helical Mesoporous Tantalum Oxide Nanotubes: Formation, Optical Activity, and Applications

      Yangyang He and Prof. Yonggang Yang

      Version of Record online: 8 MAY 2017 | DOI: 10.1002/tcr.201700012

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      Single–handed helical Ta2O5 nanotubes are prepared using chiral low-molecular-weight gelators. The morphologies are controlled by both the morphology and distribution of the cationic ions of the organic self-assemblies. Mesopores on the surfaces and within the walls are formed owing to the amorphous-to-crystalline transformation. The optical activity is proposed to partially originate from chiral point defects on the inner surfaces of the nanotubes.

    11. Luminescent Strategies for Label-free G-quadruplex-based Enzyme Activity Sensing

      Dr. Dik-Lung Ma, Zhen-Zhen Dong, Dr. Kasipandi Vellaisamy, Ka-Man Cheung, Guanjun Yang and Dr. Chung-Hang Leung

      Version of Record online: 3 MAY 2017 | DOI: 10.1002/tcr.201700014

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      This Personal Accounts describes our group's recent efforts in the development of G-quadruplex-based sensing platforms for enzyme activity. The highlighted studies showcase the versatility of the G-quadruplex motif for developing sensing assays for a variety of different enzymes.

    12. Practical Synthesis of Both Enantiomeric Amino Acid, Mannich, and Aldol Derivatives by Asymmetric Organocatalysis

      Yan Liu, Natarajan Arumugam, Abdulrahman I. Almansour, Raju Suresh Kumar and Keiji Maruoka

      Version of Record online: 27 APR 2017 | DOI: 10.1002/tcr.201700008

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      The recent development in three different, organocatalyzed asymmetric methodologies for the practical synthesis of both enantiomers is described. The synthesis of both enantiomeric products by using both enantiomeric catalysts is the most traditional way. In addition, use of two pseudoenantiomeric catalysts provides a more practical approach for the synthesis of both enantiomeric products. Even more efficient is the use of a single enantiomeric catalyst in the presence or absence of certain additives for obtaining both enantiomeric products.

    13. Supported Ionic Liquids: A Versatile and Useful Class of Materials

      Dr. Vincenzo Campisciano, Dr. Francesco Giacalone and Prof. Michelangelo Gruttadauria

      Version of Record online: 26 APR 2017 | DOI: 10.1002/tcr.201700005

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      The huge versatility of supported ionic liquids (SILs): SILs represent a very useful class of materials. In this account, we report some examples of our ongoing research dealing with the use of different SILs based catalysts for a wide range of applications such as asymmetric organocatalysis, alcohols oxidation and etherification, chemical fixation of CO2 and Pd-mediated C–C cross coupling reactions.

    14. Toward the Dark Matter of Natural Products

      Toshiyuki Wakimoto

      Version of Record online: 18 APR 2017 | DOI: 10.1002/tcr.201700009

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      Recent advancements in metabolomics, in concert with genomics analyses, have further extended the natural product diversity, prompting growing awareness of the existence of reactive or short-lived natural molecules. Nevertheless, discovering natural molecules with dynamic chemical or biological propensities from an extremely complex mixture is still challenging, even with modern analytical and isolation technologies. This personal account describes some characterizations of natural products that had not previously been isolable or detectable, due to their elusive nature.

    15. Frustrated Lewis Pair Chemistry: Searching for New Reactions

      Dr. Gerald Kehr and Prof. Gerhard Erker

      Version of Record online: 12 APR 2017 | DOI: 10.1002/tcr.201700010

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      Frustrated Lewis pairs show a number of surprising reaction modes with a variety of organic and inorganic substrates.

    16. Nanotechnology for Electroanalytical Biosensors of Reactive Oxygen and Nitrogen Species

      Dr. Rajesh Seenivasan, Charles Kolodziej, Prof. Chandran Karunakaran and Prof. Clemens Burda

      Version of Record online: 10 APR 2017 | DOI: 10.1002/tcr.201600143

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      Nanomaterials-based electroanalytical bioassays have been developed for monitoring ROS & RNS levels in cells and biological fluids to study their role in diseases and disorders. Improving their selectivity and sensitivity will make nanobio-sensors increasingly practical for wide-spread applications. This review describes recent efforts in this field toward the realization of personalized healthcare.

    17. Elucidation of biosynthetic pathways of natural products

      Shinji Kishimoto, Yuta Tsunematsu, Michio Sato and Kenji Watanabe

      Version of Record online: 7 APR 2017 | DOI: 10.1002/tcr.201700015

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      Biosynthetic pathways of fungal natural products having interesting chemical structures and valuable biological properties have been elucidated. Biosynthetic genes are identified through genome mining and genetic manipulation of the producing organism. Those genes are used for heterologous reconstitution of the biosynthetic pathway being studied in yeast or engineered fungi for preparing pathway products and intermediates. Lastly, detailed in vivo, in vitro and structural characterizations of the enzymes result in elucidation of unexpected mechanisms of secondary metabolite biosynthesis.

    18. Application of Fischer Indolization under Green Conditions using Deep Eutectic Solvents

      Sambasivarao Kotha and Chandravathi Chakkapalli

      Version of Record online: 5 APR 2017 | DOI: 10.1002/tcr.201600138

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      Indole containing polycycles such as aza-polyquinanes, cyclophanes, spirocycles and other heterocycles were synthesized by using deep eutectic media i. e. L-(+)-tartaric acid (TA) and dimethyl urea (DMU) via Fischer indolization (FI)

    19. Platinum Group Metal-free Catalysts for Hydrogen Evolution Reaction in Microbial Electrolysis Cells

      Heyang Yuan and Zhen He

      Version of Record online: 4 APR 2017 | DOI: 10.1002/tcr.201700007

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      Microbial electrolysis cells (MECs) can convert organic matter to hydrogen gas at low energy consumption. Cathode catalysts for the hydrogen evolution reaction (HER) present a major challenge for the practical applications of MECs. An ideal cathode catalyst should be catalytically active, simple to synthesize, durable in complex environment, and cost-effective. MECs in turn can serve as a research platform to study the durability of the HER catalysts.

    20. 1,8-Naphthalimide: A Potent DNA Intercalator and Target for Cancer Therapy

      Runjhun Tandon, Vijay Luxami, Harsovin Kaur, Nitin Tandon and Kamaldeep Paul

      Version of Record online: 4 APR 2017 | DOI: 10.1002/tcr.201600134

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      The development of functional 1,8-naphthalimide derivatives as DNA intercalation and anticancer agents is a fast growing area. This review gives an overwiew of the many discoveries and the progression of the use of 1,8-naphthalimides agents and their applications to date; focusing mainly on imide and ring substitution of naphthalimide and their conjugation, metal complexes with naphthalimide and bis-naphthalimide based structures. The rich photophysical properties of 1,8-naphthalimides make them prime candidates as the changes in spectroscopic properties such as absorption and fluorescence can all be used to monitor their binding.

    21. Synthesis of imidazo[1,2-a]pyridines: C-H functionalization in the direction of C-S bond formation

      Chitrakar Ravi and Dr. Prof. Subbarayappa Adimurthy

      Version of Record online: 20 MAR 2017 | DOI: 10.1002/tcr.201600146

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      In this account we described recent method developments on the synthesis of imidazo [1,2-a] pyridines using readily available starting substrates, and inexpensive catalysts under very mild conditions and their functionalization (C−S bond formation).

    22. Recent Developments in Total Syntheses of Cephalosporolides, Penisporolides, and Ascospiroketals

      Dr. Hongliang Yao, Jian Wang and Prof. Dr. Rongbiao Tong

      Version of Record online: 8 MAR 2017 | DOI: 10.1002/tcr.201700001

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      Mimicking biosynthetic hypothesis led to develop a general synthetic strategy for the total synthesis of both decanolide-type cephalosporolides and SAFL-type natural products. This biomimetic strategy features two key transformations: i) oxidative ring expansion of bicyclic β-hydroxy tetrahydropyrans to the decanolides and ii) ring contraction rearrangement of the decanolides to the tricyclic SAFLs. In particular, the phenol derivatives are exploited as the starting materials for the decanolides and then the SAFLs.

    23. Squaramide-Catalyzed Asymmetric Reactions

      Bo-Liang Zhao, Jun-Hua Li and Prof.Dr. Da-Ming Du

      Version of Record online: 7 MAR 2017 | DOI: 10.1002/tcr.201600140

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      Bifunctional squaramides have emerged as powerful hydrogen-bonding catalysts for promoting a wide array of useful asymmetric reactions, which provides convenient methods for the construction of complex molecular structures and chiral biologically active compounds. This review highlights the recent advances of our research group in the chiral squaramide-catalyzed asymmetric reactions, including Michael addition, Mannich reaction, aza-Henry reaction, Strecker reaction as well as cascade or sequential reactions.

    24. Synthesis of Functionalized Pyrazoles via 1,3-Dipolar Cycloaddition of α-Diazo-ketophosphonates, Sufones and Esters with Electron-Deficient Alkenes

      T. V. Baiju and Irishi N. N. Namboothiri

      Version of Record online: 7 MAR 2017 | DOI: 10.1002/tcr.201600141

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      1,3-Dipolar cycloaddition of α-diazo-ketophosphonate (BOR), sufone and ester with various electron deficient alkenes have been utilized for the synthesis of diverse functionalized pyrazoles. Diverse dipolarophiles such as conjugated nitroalkenes, enones and vinyl sulfones were employed for the synthesis of phosphonyl/sulfonyl pyrazoles and pyrazole esters. Efficient synthetic strategies were established for the synthesis of Withasomnine, a pyrazole alkaloid, by using 1,3-dipolar cycloaddition of a diazo compound as the key step.

    25. Thioether-Derived Macrocycle for Peptide Secondary Structure Fixation

      Yuan Tian, Dan Yang, Xiyang Ye and Zigang Li

      Version of Record online: 3 MAR 2017 | DOI: 10.1002/tcr.201600137

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      In this personal account, thioether-derived macrocyclization methods developed by our group for stabilization of α-helix, type-III β turn and β-hairpin conformations are discussed.

    26. Towards More Efficient, Greener Syntheses Through Flow Chemistry

      Justin A.M. Lummiss, Peter D. Morse, Rachel L. Beingessner and Timothy F. Jamison

      Version of Record online: 28 FEB 2017 | DOI: 10.1002/tcr.201600139

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      Intersection of Green and Flow Chemistry. The principles of green chemistry identify the major challenges in achieving efficient, sustainable, and safe chemical transformations. Continuous flow platforms represent an enabling technology for improving reaction efficiency and reducing waste production. The intersection of these fields offers exciting possibilities for improved chemical synthesis.

    27. Self–assembly of renewable  nano–sized triterpenoids

      Prof. Braja Gopal Bag and Dr. Rakhi Majumdar

      Version of Record online: 14 FEB 2017 | DOI: 10.1002/tcr.201600123

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      Spontaneously self-assembly of renewable nano-sized triterpenoids has been demonstrated in different liquids yielding supramolecular architectures of nano- to micrometer dimensions.

    28. Organocatalytic Hydrophosphonylation Reaction of Carbonyl Groups

      Dr. Raquel P. Herrera

      Version of Record online: 7 FEB 2017 | DOI: 10.1002/tcr.201600129

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      This revision is covering the limited examples reported for a pivotal strategy in the formation of C−P bonds such as the asymmetric organocatalytic hydrophosphonylation of carbonyl groups (Pudovik reaction). The scope and limitations, and the proposed mechanisms for the scarce different possibilities of asymmetric induction are also shown. The recent evolution and future trends of this undeveloped approach are commented.

    29. Catalytic reaction assisted by plasma or electric field

      Shuhei Ogo and Yasushi Sekine

      Version of Record online: 1 FEB 2017 | DOI: 10.1002/tcr.201600127

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      Low-temperature conversion of methane and other hydrocarbons, as well as alcohol, can be achieved at lower temperatures using plasma or an electric field and catalysts. A hybrid system of non-equilibrium plasma and catalyst provided high conversion and selectivity for products by virtue of high electron temperature and strong adsorption on catalyst. Imposing a DC electric field on the catalyst bed also promotes a catalytic reaction, even at low temperatures.

    30. Hydrodynamic Effects in Soft-Matter Self-Assembly: The Case of J-Aggregates of Amphiphilic Porphyrins

      Prof. Josep M. Ribo, Dr. Zoubir El-Hachemi, Dr. Oriol Arteaga, Dr. Adolf Canillas and Dr. Joaquim Crusats

      Version of Record online: 20 JAN 2017 | DOI: 10.1002/tcr.201600133

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      The chiral J-aggregates of achiral amphiphilic porphyrins show hydrodynamic effects on their nanoparticles and selectivity on the nanoparticle growths, which represent a simple paradigm on the effect of macroscopic forces on the morphology and structure of supramolecular species obtained by self-assembly.

    31. Functionalization of C-H Bonds by Photoredox Catalysis

      Functionalization of C-H Bonds by Photoredox Catalysis

      Qixue Qin, Heng Jiang, Zhentao Hu, Daan Ren and Shouyun Yu

      Version of Record online: 11 JAN 2017 | DOI: 10.1002/tcr.201600125

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      Visible-light photoredox-catalyzed functionalization of inert C−H bonds including C(sp2)-H bonds of arenes and C(sp3)-H bonds of aliphatic compounds has been reviewed.

    32. Azobenzene: A Photoactive Building Block for Supramolecular Architectures

      Massimo Baroncini and Giacomo Bergamini

      Version of Record online: 5 JAN 2017 | DOI: 10.1002/tcr.201600112

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      In this Account we report some examples in which azobenzene moieties are contained into supramolecular structures and how the photoisomerization achieves precise and clean control on some of their properties. These results highlight how this outstanding photochrome can be used to develop molecular devices and machines with light-induced functionalities.

    33. Emerging of Inorganic Hole Transporting Materials For Perovskite Solar Cells

      Ramireddy Rajeswari, Madoori Mrinalini, Seelam Prasanthkumar and Lingamallu Giribabu

      Version of Record online: 4 JAN 2017 | DOI: 10.1002/tcr.201600117

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      Recently, hole transport materials based on inorganic metal oxides have rapidly increased in place of organic materials like spiro due to stability, ease of synthesis and low cost for perovskite solar cells. The device efficiency using inorganic hole transport materials have crossed 19% which is on par with spiro based devices. This review covers recent developments on inorganic based hole transport materials for perovskite solar cells.

    34. Asymmetric Multicomponent Reactions Based on Trapping of Active Intermediates

      Asymmetric Multicomponent Reactions Based on Trapping of Active Intermediates

      Dan Zhang and Wenhao Hu

      Version of Record online: 4 JAN 2017 | DOI: 10.1002/tcr.201600124

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      In this personal account, novel asymmetric multicomponent reactions (MCRs) by trapping of active ylide/zwitterionic intermediates with electrophiles are presented. These novel MCRs not only provide experimental evidences to support the existence of protic onium ylides intermediates/zwitterionic intermediates, but also offer new approaches for the efficient and rapid construction of chiral polyfunctional molecules.

    35. Photodynamic Therapy: Past, Present and Future

      Ushasri Chilakamarthi and Lingamallu Giribabu

      Version of Record online: 2 JAN 2017 | DOI: 10.1002/tcr.201600121

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      Photodynamic therapy is emerging as an alternative treatment modality to treat cancer due to its affordability and accessibility. The delivery vehicles like liposomes and nanoparticles guided by tumor specific peptides are making this treatment more specific to cancer cells avoiding the undesirable side effects. In this review we have discussed the development of three generations of PS, delivery strategies, development of immunity, combination therapy and future prospects.

    36. Azidoimidazolinium Salts: Safe and Efficient Diazo-transfer Reagents and Unique Azido-donors

      Mitsuru Kitamura

      Version of Record online: 21 DEC 2016 | DOI: 10.1002/tcr.201600118

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      2-Azido-1,3-dimethylimidazolinium chloride (ADMC) and its corresponding hexafluorophosphate (ADMP) were found to be efficient diazo-transfer reagents to various organic compounds. ADMP was isolated as a crystal having thermal stability and low explosibility characteristics. In addition to their diazo-transfer ability (N2 donor), azidoimidazolinium salts showed unique reactivity for azidation (N3 donor) and migratory amidation.

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