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Contents list for Chemical Communications, issue 34, 2009

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Front cover
Chem. Commun., 2009, 5045
DOI: 10.1039/b915904p

front cover image for Chemical Communications, Issue 34, 2009

Inside front cover
Chem. Commun., 2009, 5046
DOI: 10.1039/b915905n

Contents and Highlights in Chemical Technology
Chem. Commun., 2009, 5047
DOI: 10.1039/b915906c

Feature Articles

Catalytic C–H amination: recent progress and future directions
Florence Collet, Robert H. Dodd and Philippe Dauban,  Chem. Commun., 2009, 5061
DOI: 10.1039/b905820f

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Recent developments within the last three years in catalytic C–H amination via either C–H insertion or activation are discussed. Particular emphasis is laid on the efficiency, as well as the chemo-, regio- and stereoselectivity of the newly discovered protocols.

Alkyne activation with Brønsted acids, iodine, or gold complexes, and its fate leading to synthetic application
Yoshinori Yamamoto, Ilya D. Gridnev, Nitin T. Patil and Tienan Jin,  Chem. Commun., 2009, 5075
DOI: 10.1039/b909978f

graphical abstract image (ID: b909978f)

Cyclization processes catalyzed or promoted by H+, I+ and transition-metal (mainly gold and platinum) salts and complexes have been described.

Communications

Ruthenium-catalyzed transformation of alkenyl triflates to alkenyl halides
Eiji Shirakawa, Yusuke Imazaki and Tamio Hayashi,  Chem. Commun., 2009, 5088
DOI: 10.1039/b907761h
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Various cyclic and acyclic alkenyl triflates, which can be prepared from readily available ketones or aldehydes in a regioselective manner, are transformed to the corresponding halides by simply mixing with a lithium halide in the presence of a ruthenium catalyst. This is the first direct transformation of alkenyl triflates to halides under transition metal catalysis.

Oligobenzamide proteomimetic inhibitors of the p53–hDM2 protein–protein interaction
Jeffrey P. Plante, Thomas Burnley, Barbora Malkova, Michael E. Webb, Stuart L. Warriner, Thomas A. Edwards and Andrew J. Wilson,  Chem. Commun., 2009, 5091
DOI: 10.1039/b908207g
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Developing general strategies for inhibition of protein–protein interactions is a key challenge in chemical biology. Herein we describe oligobenzamide inhibitors of the p53–hDM2 protein–protein interaction.

Dialysis process for the removal of surfactants to form colloidal mesoporous silica nanoparticles
Chihiro Urata, Yuko Aoyama, Akihisa Tonegawa, Yusuke Yamauchi and Kazuyuki Kuroda,  Chem. Commun., 2009, 5094
DOI: 10.1039/b908625k
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Colloidal mesoporous silica nanoparticles less than 20 nm in diameter are prepared by dialysis; this simple surfactant removal route can avoid aggregation by sedimentation–redispersion and remove cationic surfactants, which is applicable to the preparation of primary nanoparticles carrying functional organic substances.

A block PCP crystal: anisotropic hybridization of porous coordination polymers by face-selective epitaxial growth
Shuhei Furukawa, Kenji Hirai, Yohei Takashima, Keiji Nakagawa, Mio Kondo, Takaaki Tsuruoka, Osami Sakata and Susumu Kitagawa,  Chem. Commun., 2009, 5097
DOI: 10.1039/b909993j

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By face-selective epitaxial growth, two porous coordination polymers (PCPs) were anisotropically integrated into one single crystal. Similar to block copolymers, this type of crystal configuration can be recognized as a block PCP crystal.

Silica nanoparticle supported lipid bilayers for gene delivery
Juewen Liu, Alison Stace-Naughton and C. Jeffrey Brinker,  Chem. Commun., 2009, 5100
DOI: 10.1039/b911472f
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Silica nanoparticles fuse with cationic liposomes to form supported bilayers, which are effective transfection agents for delivering plasmid DNAs to mammalian cells.

Perfluorinated nitrosopyrazolone-based erbium chelates: a new efficient solution processable NIR emitter
Luca Beverina, Maurizio Crippa, Mauro Sassi, Angelo Monguzzi, Francesco Meinardi, Riccardo Tubino and Giorgio A. Pagani,  Chem. Commun., 2009, 5103
DOI: 10.1039/b906494j
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We show the design and synthesis of new solution processable perfluorinated erbium chelates possessing a NIR emission with lifetimes as long as 16 s.

Enhanced fluorescence sensing of amine vapor based on ultrathin nanofibers
Yanke Che and Ling Zang,  Chem. Commun., 2009, 5106
DOI: 10.1039/b913138h
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The fluoresence sensing sensitivity of perylene based nanofibril films for amine vapor was largely enhanced upon using ultrathin nanofibers, which were fabricated through a new solution-based self-assembly process. The unprecedented sensitivity obtained hereby may provide the sensing system broad applications in the practical trace vapor detection of amines.

Robust synthesis of bismuth titanate pyrochlore nanorods and their photocatalytic applications
Sankaran Murugesan and Vaidyanathan (Ravi) Subramanian,  Chem. Commun., 2009, 5109
DOI: 10.1039/b904539b
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A facile and template-free reverse micelle-based method to synthesize highly crystalline and pure stoichiometric bismuth titanate (Bi2Ti2O7) pyrochlore nanorods 400–500 nm long and 40–50 nm in diameter which demonstrate promising photoactivity.

Oxidative degradation of oligo(ethylene glycol)-terminated monolayers
Guoting Qin and Chengzhi Cai,  Chem. Commun., 2009, 5112
DOI: 10.1039/b911155g

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The observation that oligo(ethylene glycol) (OEG)-terminated monolayers remained highly protein-resistant for a month at 37 °C in PBS buffer while they degraded faster in air can be rationalized by a proposed mechanism formulated from a model study using the first internal hydroperoxide of OEG.

Brookite TiO2 nanoflowers
Bin Zhao, Feng Chen, Qiwei Huang and Jinlong Zhang,  Chem. Commun., 2009, 5115
DOI: 10.1039/b909883f

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Pure brookite TiO2 nanoflowers consisting of single crystalline nanorods were synthesized for the first time using a facile one-step hydrothermal route, and a formation mechanism was proposed based on our experimental results.

Microwave synthesis of fluorescent carbon nanoparticles with electrochemiluminescence properties
Hui Zhu, Xiaolei Wang, Yali Li, Zhongjun Wang, Fan Yang and Xiurong Yang,  Chem. Commun., 2009, 5118
DOI: 10.1039/b907612c

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In this study, we present a facile, economical microwave pyrolysis approach to synthesize fluorescent carbon nanoparticles with electrochemiluminescence properties.

Inversion of product selectivity in an enzyme-inspired metallosupramolecular tweezer catalyzed epoxidation reaction
Pirmin A. Ulmann, Adam B. Braunschweig, One-Sun Lee, Michael J. Wiester, George C. Schatz and Chad A. Mirkin,  Chem. Commun., 2009, 5121
DOI: 10.1039/b908852k
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A heteroligated PtII–P,S tweezer coordination complex that combines an epoxidation catalyst with an amidopyridine receptor leads to an inversion of the product distribution.

Growth of germanium nanowires using liquid GeCl4 as a precursor: the critical role of Si impurities
Hyun Jae Song, Seok Min Yoon, Hyun-Joon Shin, Hyunseob Lim, Chibeom Park and Hee Cheul Choi,  Chem. Commun., 2009, 5124
DOI: 10.1039/b908361h
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Liquid GeCl4 precursors have been employed to grow into one dimensional Ge nanowires (NWs) via a vapor–liquid–solid (VLS) process, in which Si, supplied as a form of liquid SiCl4, plays a critical role for the successful formation of Ge NWs.

Glycosyl–nucleoside–lipid based supramolecular assembly as a nanostructured material with nucleic acid delivery capabilities
Guilhem Godeau, Julie Bernard, Cathy Staedel and Philippe Barthélémy,  Chem. Commun., 2009, 5127
DOI: 10.1039/b906212b

graphical abstract image (ID: b906212b)

Glycosyl–nucleoside–lipids self assemble to give highly organized structures such as fibers and nanotubes, which can stabilize hydrogels. Carbohydrate moieties provide a suitable environment to complex, transport and deliver nucleic acids into human cells.

Synthesis and characterization of highly pure azido-functionalized polyhedral oligomeric silsesquioxanes (POSS)
Vuthichai Ervithayasuporn, Xin Wang and Yusuke Kawakami,  Chem. Commun., 2009, 5130
DOI: 10.1039/b909802j

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Cage rearrangement of polyhedral oligomeric silsesquioxane (POSS) T8 toward T10 and T12 structures was firstly discovered in the azidation reaction.

A triblock fluorous surfactant as a specific gelator for perfluorocarbons
Jiaan Gan, Mounir El Bakkari, Colette Belin, Chrystèle Margottin, Pascale Godard, Jean-Luc Pozzo and Jean-Marc Vincent,  Chem. Commun., 2009, 5133
DOI: 10.1039/b908820b
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The double-tailed triblock surfactant 1-Na represents a new type of gelator for perfluorocarbons which can gelate at low concentration both bromoperfluorooctane and perfluorodecalin, two of the most appealing perfluorinated fluids for pharmaceutical applications.

Total synthesis of (+)-virgatusin via AlCl3-catalyzed [3+2] cycloaddition
Shanina D. Sanders, Andrea Ruiz-Olalla and Jeffrey S. Johnson,  Chem. Commun., 2009, 5135
DOI: 10.1039/b911765b
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A stereocontrolled asymmetric synthesis of virgatusin was achieved in five steps from donor–acceptor cyclopropane 1 employing a Lewis acid-catalyzed cyclopropane–aldehyde addition reaction that constructs the tetrahydrofuran.

Direct catalytic asymmetric aldol reaction of -keto esters with formaldehyde promoted by a dinuclear Ni2-Schiff base complex
Shinsuke Mouri, Zhihua Chen, Shigeki Matsunaga and Masakatsu Shibasaki,  Chem. Commun., 2009, 5138
DOI: 10.1039/b912380f
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A homodinuclear Ni2-Schiff base-catalyzed direct asymmetric hydroxymethylation of -keto esters gave products in up to 94% ee with catalyst turnover number (TON) up to 940.

Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C–H bond cleavage
Tatsuya Fukutani, Nobuyoshi Umeda, Koji Hirano, Tetsuya Satoh and Masahiro Miura,  Chem. Commun., 2009, 5141
DOI: 10.1039/b910198e

graphical abstract image (ID: b910198e)

The rhodium-catalyzed oxidative coupling of aromatic imines with alkynes effectively proceeds via regioselective C–H bond cleavage to produce indenone imine and isoquinoline derivatives.

Boiling water-catalyzed neutral and selective N-Boc deprotection
Jia Wang, Yan-Liang Liang and Jin Qu,  Chem. Commun., 2009, 5144
DOI: 10.1039/b910239f

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A general protocol for removing Boc groups from various types of nitrogen is reported. A preliminary investigation of the reaction mechanism indicates that water acts as a dual acid/base catalyst at elevated temperature.

Spirocyclic boronium ions: precursors to persistent neutral radicals
Thomas K. Wood, Warren E. Piers, Brian A. Keay and Masood Parvez,  Chem. Commun., 2009, 5147
DOI: 10.1039/b911982e

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Reduction by one electron of two spirocyclic boronium ions stabilized by bipyridine donors leads to isolable, persistent boron-based neutral radicals.

One-pot cascade Michael–Michael–Aldol condensation for diastereoselective synthesis of nitro-substituted cyclohexanes
Yunfeng Chen, Cheng Zhong, Xiaohua Sun, Novruz G. Akhmedov, Jeffrey L. Petersen and Xiaodong Shi,  Chem. Commun., 2009, 5150
DOI: 10.1039/b909766j

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A highly efficient one-pot synthesis of functional group-enriched cyclohexanes for the stereoselective synthesis of poly-N-heterocycles.

Highly active gold-based catalyst for the reaction of benzaldehyde with ethyl diazoacetate
Manuel R. Fructos, M. Mar Díaz-Requejo and Pedro J. Pérez,  Chem. Commun., 2009, 5153
DOI: 10.1039/b908233f

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The gold complex [IPrAu(NCMe)]BF4 catalyzes the reaction of ethyl diazoacetate with benzaldehyde to give mixtures of ethyl 3-oxo-3-phenylpropanoate and ethyl 3-hydroxy-2-phenylacrylate in the first example of a group 11 metal-based catalyst for this transformation.

5,15-Bis(di-p-anisylamino)-10,20-diphenylporphyrin: distant and intense electronic communication between two amine sites
Ryota Sakamoto, Taishiro Sasaki, Norikazu Honda and Takeshi Yamamura,  Chem. Commun., 2009, 5156
DOI: 10.1039/b907413a
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Distant and intense electronic communication between two amine sites through a porphyrin -spacer was quantified for the first time with inter-valence charge transfer (IVCT) band analyses.

A simple and efficient oxidation of alcohols with ruthenium on carbon
Shigeki Mori, Masato Takubo, Kazuya Makida, Takayoshi Yanase, Satoka Aoyagi, Tomohiro Maegawa, Yasunari Monguchi and Hironao Sajiki,  Chem. Commun., 2009, 5159
DOI: 10.1039/b908451g

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A simple, efficient, and environmentally-friendly heterogeneous Ru/C-catalyzed oxidation of secondary and primary alcohols without additives under an atmosphere of oxygen has been established.

Photoisomerization of matrix isolated F2CS into cis and trans FCSF
Xiaoqing Zeng, Helmut Beckers and Helge Willner,  Chem. Commun., 2009, 5162
DOI: 10.1039/b911638a

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Both cis and trans isomers of FCSF were generated by irradiation of Ar matrix isolated F2CS at 16 K with an ArF excimer laser ( = 193 nm).

Rapid synthesis of 3-cyanopyridine-derived chromophores with two-dimensional tunability and solvatochromic photophysical properties
Mark C. Bagley, Zhifan Lin and Simon J. A. Pope,  Chem. Commun., 2009, 5165
DOI: 10.1039/b910664b
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Cyanopyridines with unusual and tunable photophysical and solvatochromic behaviour are produced rapidly and efficiently by a tandem oxidation/Bohlmann–Rahtz reaction under microwave irradiation followed by copper-mediated N-arylation.

Detection of low-populated reaction intermediates with hyperpolarized NMR
Pernille R. Jensen, Sebastian Meier, Jan H. Ardenkjær-Larsen, Jens Ø. Duus, Magnus Karlsson and Mathilde H. Lerche,  Chem. Commun., 2009, 5168
DOI: 10.1039/b910626j

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Nuclear spin polarization enhancement was applied in enzymatic in vitro assays for the detection of transient reaction intermediates. Otherwise elusive intermediates can become directly detectable at concentrations below micromolar to aid the determination of reaction mechanisms.

Catalytic dehydrative etherification and chlorination of benzyl alcohols in ionic liquids
Hassan A. Kalviri, Chad F. Petten and Francesca M. Kerton,  Chem. Commun., 2009, 5171
DOI: 10.1039/b909866f
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A simple catalytic system consisting of Pd(CH3CN)2Cl2 in a hydrophobic ionic liquid can perform the direct condensation of substituted benzyl alcohols to give ethers, while in the presence of NH4Cl, benzyl chloride is obtained in excellent yield.

Polyoxometalate-supported Pd nanoparticles as efficient catalysts for the direct synthesis of hydrogen peroxide in the absence of acid or halide promoters
Miao Sun, Jizhe Zhang, Qinghong Zhang, Ye Wang and Huilin Wan,  Chem. Commun., 2009, 5174
DOI: 10.1039/b910317a

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Keggin-type polyoxometalate (Cs1.5H1.5PW12O40)-supported Pd nanoparticles catalyse the direct synthesis of H2O2 efficiently in the absence of any acid or halide promoters.

Preparation of hollow silica spheres with holes on the shells
Yuanli Chen, Yi Li, Yuxia Chen, Xiaojuan Liu, Ming Zhang, Baozong Li and Yonggang Yang,  Chem. Commun., 2009, 5177
DOI: 10.1039/b903859k

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Hollow silica spheres with holes on the shells were prepared using L- 16Ala6PyBrvia a sol–gel method.

Catalytic asymmetric Strecker hydrocyanation of imines using Yb(OTf)3–pybox catalysts
Babak Karimi and Aziz Maleki,  Chem. Commun., 2009, 5180
DOI: 10.1039/b908854g

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Yb(OTf)3–pybox complexes have been used to catalyze the enantioselective Strecker hydrocyanation of a wide range of aldimines with good to excellent yields and up to 98% ee.

Back cover
Chem. Commun., 2009, 5183
DOI: 10.1039/b915908h