13
Chemistry Letters http://www.csj.jp/journals/chem-lett/ Vol.37 No.1 CMLTAG January, 2008 ISSN 0366-7022 Copyright Ó 2008 The Chemical Society of Japan 2 Development of Chiral Bicyclic Triazolium Salt Organic Catalysts: The Importance of the N-Aryl Substituent N N N O BF 4 N N N O BF 4 OMe F F F F F more nucleophilic less basic, longer lived Tomislav Rovis doi:10.1246/cl.2008.2 The development of a family of chiral bicyclic triazolium salts is described. Treatment of these salts with base provides a nucleophilic carbene which may be used as an organic catalyst for asymmetric acyl anion chemistry including the benzoin and Stetter reactions, and some recently developed redox chemistry. Throughout the development of these reactions, the nature of the N-aryl substituent on the triazole ring has proven to have a profound effect on both reactivity and selectivity. These observations have also paralleled those made by others using our family of catalysts. Highlight Review Letter 8 Base-promoted Condensation Polymeriza- tion of Aminoesters with Diphenylacetylene and trans-Stilbene Backbones Akihiro Yokoyama, Yuuki Shimizu, Jun-ichiro Saito, and Tsutomu Yokozawa doi:10.1246/cl.2008.8 Electronic Supporting Information

Chemistry Letters E–E Bonds (E = Si and Ge) BuLi Li Li ClR2EER2Cl 1:(E=Si,R=Me), 2a:(E=Ge,R=Me), 2b:(E=Ge,R=iPr) E E E R R R R RR R Et2O, -78 C r.t hν( λ=254 nm) Ge Ge Me Me Me

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Chemistry Lettershttp://www.csj.jp/journals/chem-lett/

Vol.37 No.1 CMLTAGJanuary, 2008 ISSN 0366-7022

Copyright � 2008 The Chemical Society of Japan

2 Development of Chiral Bicyclic TriazoliumSalt Organic Catalysts: The Importance ofthe N-Aryl Substituent

N

N N

O BF4 N

N N

O BF4

OMe

FF

F

FF

more nucleophilic less basic, longer lived

Tomislav Rovisdoi:10.1246/cl.2008.2

The development of a family of chiral bicyclic triazolium salts is described. Treatment of these salts with base provides anucleophilic carbene which may be used as an organic catalyst for asymmetric acyl anion chemistry including the benzoinand Stetter reactions, and some recently developed redox chemistry. Throughout the development of these reactions, thenature of the N-aryl substituent on the triazole ring has proven to have a profound effect on both reactivity and selectivity.These observations have also paralleled those made by others using our family of catalysts.

Highlight Review

Letter

8 Base-promoted Condensation Polymeriza-tion of Aminoesters with Diphenylacetyleneand trans-Stilbene Backbones

Akihiro Yokoyama, Yuuki Shimizu, Jun-ichiroSaito, and Tsutomu Yokozawadoi:10.1246/cl.2008.8Electronic Supporting Information

C-2 Chemistry Letters Vol.37, No.1 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

10 A Proline-based Macrocyclic Amide with S4Symmetry

Hee Choon Ahn, Sun-mi Yun, and Kihang Choidoi:10.1246/cl.2008.10

12 Tailoring Liquid-crystalline SupramolecularStructures by Ionic Interactions

SA Colhex

NNH2

NH2

H2N

HO

O

OC8H17

OC8H17

+

Takao Noguchi, Keiki Kishikawa, and ShigeoKohmotodoi:10.1246/cl.2008.12Electronic Supporting Information

14 Sustaining Effect of Gold Colloids on theAmorphous Titanium Dioxide Particles

Methyl Orange

CommercialTiO2

Au/TiO2

complex particles

Photoimage for decomposition of MO solution irradiated with visible light ( ≥470 nm).λ

Mariko Takayanagi, Yoko Imai, and KazuoTajimadoi:10.1246/cl.2008.14

16 Solvatochromic Luminescence Based on theExcimer Formation of Bipyridine Plati-num(II) Complexes with Linear AlkylChains

Masako Kato, Yasuko Shishido, Yukiko Ishida,and Shinobu Kishidoi:10.1246/cl.2008.16Electronic Supporting Information

18 Utilization of Nanometre-order DiameterColumns inside Porous Anodic Alumina forChromatography Chip System

Tomohisa Yamashita, Shuji Kodama, MikiyaOhto, Eriko Nakayama, Tomoko Kemmei,Tatsuya Muramoto, Akira Yamaguchi, NorioTeramae, and Nobutaka Takayanagidoi:10.1246/cl.2008.18Electronic Supporting Information

Chemistry Letters Vol.37, No.1 (2008) C-3

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

20 Synthesis, Structural Characterization, andPhotolysis of Dibenzodehydro[16]annulenesContaining E–E � Bonds (E = Si and Ge)

BuLiLi

Li

ClR2EER2Cl

1:(E=Si,R=Me), 2a:(E=Ge,R=Me), 2b:(E=Ge,R=iPr)

E

E

E

ER R R R

R R R R

Et2O, -78 °C r.t

hν ( λ=254 nm)Ge

Ge

MeMe

Me Me

+C6D12 , r.t., 30 min

2a

3

:GeMe2

Kunio Mochida, Junichi Ohto, Matsuri Masuda,Masato Nanjo, Hidekazu Arii, and YasuhiroNakadairadoi:10.1246/cl.2008.20Electronic Supporting Information

22 A Facile KF/Al2O3-mediated, One-pot Syn-thesis of Symmetrical Trithiocarbonatesfrom Alkyl Halides and Carbon Disulfide

A facile, efficient, and convenient method has been developed for the one-pot synthesis ofsymmetrical trithiocarbonates from carbon disulfide and various alkyl halides in the presence ofKF/Al2O3 in DMF at room temperature.

2 R-X + 3 CS2

S

S

R

S

RKF/Al2O3

DMF, 25 °C, airBarahman Movassagh, Mohammad Soleiman-Beigi, and Mohammad Nazaridoi:10.1246/cl.2008.22

24 A Novel TTF-based Electron-donor withImidazole-annelation Having Hydrogen-bonding and Proton-transfer Abilities

Yasushi Morita, Yosuke Yamamoto, YumiYakiyama, Tsuyoshi Murata, and KazuhiroNakasujidoi:10.1246/cl.2008.24Electronic Supporting Information

26 Lewis Base Catalyzed 1,3-Dithiane Additionto Carbonyl Compounds Using 2-Trimethyl-silyl-1,3-dithiane

R1 R2

O+

(1.5 equiv.)S

STMS

R1 R2

HO S

SPhONn-Bu4 (30 mol %)

DMF, 0 °C−rt, 1 h

H+

up to 97%

Makoto Michida and Teruaki Mukaiyamadoi:10.1246/cl.2008.26

28 3-Iodo-3-trimethylsilylpropenal as a UsefulUnit for Pinacol Coupling and SubsequentFunctional Group Transformations

TiI4-mediated pinacol coupling reaction of (Z)-3-iodo-3-trimethylsilylpropenal is used for thepreparation of trans-4,5-bis[(Z)-2-iodo-2-(trimethylsilyl)vinyl]-2,2-dimethyl-1,3-dioxolane,which is utilized for the subsequent C−C bond-forming reactions.

O

TMS

I

TMS

I

TMS

I

H

O

TMS

I

TMS

I

HO

OH

TiI4 (2.0 equiv.)

EtCN

OO O

R

R'

R

R'Makoto Shimizu, Hisashi Okimura, NobuyukiManabe, and Iwao Hachiyadoi:10.1246/cl.2008.28

C-4 Chemistry Letters Vol.37, No.1 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

30 Intermediate-range Order in MesoporousSilicas Investigated by a High-energy X-rayDiffraction Technique

Toru Wakihara, Wei Fan, Shinji Kohara,Masaru Ogura, Gopinathan Sankar, and TatsuyaOkubodoi:10.1246/cl.2008.30Electronic Supporting Information

32 Observation of Arsenic Transfer in LeafTissue of Hyperaccumulator Fern by Utiliz-ing Synchrotron Radiation Micro-XRFImaging

As

100 µmIntensity(cps)0 2250

Ca

Intensity(cps)0 3850

K

Intensity(cps)0 5670100 µm 100 µm

Evidence of As transfer from root to leaf only in 1 h after feeding, as revealed by SR-micro-XRF imaging.

Nobuyuki Kitajima, Teruhiko Kashiwabara,Naoki Fukuda, Satoshi Endo, Akiko Hokura,Yasuko Terada, and Izumi Nakaidoi:10.1246/cl.2008.32

34 Solvo-thermal Preparation of Cadmium Tel-luride Nanoparticles from a Novel SingleSource Molecular Precursor

A convenient solvo-thermal route has been developed for the preparation of cadmium telluridenanoparticles using a novel single-source molecular precursor. The prepared nanoparticles havebeen characterized by X-ray diffraction, SEM, and TEM.

a) SEM and b) TEM images of cadmium telluride nanoparticles.

a b

D. Selvakumar, Santosh Kumar Tripathi,Rajendra Singh, and M. Nasimdoi:10.1246/cl.2008.34

36 Quasi-solid Polymer Electrolytes Based onPolyacrylonitrile and Plasticizers for Indo-line Dye Sensitized Solar Cells of Efficiency5.3%

0

2

4

6

8

10

12

14

16

0.0 0.2 0.4 0.6 0.8

Voltage/V

Cur

rent

den

sity

/mA

cm

-2

Fabrication of quasi-solid-state solar

sensitized by the organic dye indoline

polymer with ethylene carbonate and

incorporating tetrabutylammonium

achieved under AM1.5 irradiation.

cells based on nanostructured TiO2

is reported here for the first time. Theelectrolyte is based on polyacrylonitrile

propylene carbonate as plasticisers

iodide (0.70 M) and iodine (0.14 M).Conversion efficiency of 5.3% was

Oliver A. Ileperuma, G. R. Asoka Kumara, andKenji Murakamidoi:10.1246/cl.2008.36

38 Deuteration and Dimerization of Acetylenewith a Nieuwland Catalyst in DeuteriumOxide

HC CH HC CD DC CD CDCD2=C(D)C

a Nieuwland Catalyst/D2O

Takashi Tachiyama, Makoto Yoshida,Tatsuhiro Aoyagi, and Shunichi Fukuzumidoi:10.1246/cl.2008.38

Chemistry Letters Vol.37, No.1 (2008) C-5

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

40 Regio- and Stereoselective HydrothiolationReactions of Ynamides with Diphenyldithio-phosphinic Acid: Straightforward Synthesisof Ketene N,S-Acetal Derivatives

C CR NTs

MeP

S

HS PhPh

DME, rt, 1 hN

S

TsMe

P

S

PhPh

(1.2 equiv.)R

R = H, Me, Ar, TMS

+

Hiroto Yasui, Hideki Yorimitsu, and KoichiroOshimadoi:10.1246/cl.2008.40

42 Complete Oxidation of Ethylene at Temper-atures below 100 �C over a Pt/Ce0:64Zr0:16-Bi0:20O1:90/�-Al2O3 Catalyst

Nobuhito Imanaka, Toshiyuki Masui, AsakoTerada, and Hayato Imadzudoi:10.1246/cl.2008.42Electronic Supporting Information

44 Micrometer-scaled Channel Lengths ofOrganic Field-effect Transistors Patternedby Using PEDOT/PSS Microfibers Channel patterns of organic

ca. 5 µm, were easily fabricated

microfibers with diameters of ca.

field-effect transistors (OFET),in which channel lengths were

by using wet-spun poly(3,4-

styrenesulfonate) (PEDOT/PSS)

5 µm.

ethylenedioxythiophene)/poly(4-

Hu Yan, Tsubasa Kagata, Yusaku Mori, YukoHarashina, Yusuke Hara, and Hidenori Okuzakidoi:10.1246/cl.2008.44Electronic Supporting Information

46 Overall Water Splitting by RuO2-loadedHexagonal YInO3 with a Distorted TrigonalBipyramid

Naoki Arai, Nobuo Saito, Hiroshi Nishiyama,Yoshiki Shimodaira, Hisayoshi Kobayashi,Yasunobu Inoue, and Kazunori Satodoi:10.1246/cl.2008.46

48 Separation of AmIII from EuIII Using anImproved System of Flow-counterbalancedCapillary Electrophoresis

241AmIII was completely separated from 152,154EuIII using an improved system of FCCE in anaqueous thiocyanate medium.

0.0

0.2

0.4

0.6

0.8

1.0

Cathode bathAnode bathAmIIIAmIII EuIII

Rat

io o

f ra

dioa

ctiv

ity

EuIII

∆H = 0 cm ∆H = 5.5 cm

0.0

0.2

0.4

0.6

0.8

1.0

Cathode bathAnode bathAmIIIAmIII EuIII

Rat

io o

f ra

dioa

ctiv

ity

EuIII

Tomotaka Mori, Yasuo Ishii, KazunoriHayashi, Makoto Yanaga, Isamu Satoh, andHideo Suganumadoi:10.1246/cl.2008.48

C-6 Chemistry Letters Vol.37, No.1 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

50 One-step Synthesis of Dibutyl Furandicar-boxylates from Galactaric Acid

HOOC C

H

OH

C

OH

H

C

OH

H

C

H

OH

COOH C4H9OHH2SO4

O COOC4H9C4H9OOC O COOC4H9

COOC4H9

5 H2O

+Reflux with Dean-Stark trap

+

2 3

+

Yoichi Taguchi, Akihiro Oishi, and Hiroshi Iidadoi:10.1246/cl.2008.50

52 Synthesis of Staudinger-type MolecularProbe for Catch-and-release Purification ofthe Binding Protein for Potassium Isolespe-dezate, a Leaf-closing Substance of Legumi-nous Plant

Matrix

MeOOC

Ph2P

SS

HN

O

Ph2PMatrix

SHLinkerS

S N3Linker

DTT

ONH

HO

OHO

OH

OOC

O

OS

SHN

OO

HN

ON3

Azide-containing phtoaffinity probe (1)

BPH2N

O

Tomohiko Fujii, Nobuki Kato, Izumi Iwakura,Yoshiyuki Manabe, and Minoru Uedadoi:10.1246/cl.2008.52

54 Fabrication of Carbon Nanostructures byPulsed Electric Discharge between MetalElectrodes Using Fluorine-containing Or-ganic Liquid

Katsuhiko Hosoi, Shin-ichi Kuroda, and HitoshiKubotadoi:10.1246/cl.2008.54

56 Infrared Spectroscopic Study of MolecularFastening by Mechanical Compression inan Elastic Film

Hiroyuki Kakuda, Norihiro Yamada, MakiAkita, Sayaka Yoshida, Yukie Kiuchi, andTakeshi Hasegawadoi:10.1246/cl.2008.56

58 Slipping and Rolling Ratio of Sliding Accel-eration for a Water Droplet Sliding on Fluo-roalkylsilane Coatings of Different Rough-ness

Sheet-shaped Ar laser beam

Tilted at 35o

Droplet

Sample

High-speed camera

Fluorescent particle

Sheet-shaped laser beam (ca. 200 µm width)

Direct observation of internal fluidity

Shunsuke Suzuki, Akira Nakajima, MunetoshiSakai, Yuu Sakurada, Naoya Yoshida, AyakoHashimoto, Yoshikazu Kameshima, andKiyoshi Okadadoi:10.1246/cl.2008.58Electronic Supporting Information

Chemistry Letters Vol.37, No.1 (2008) C-7

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

60 Fluorescence Resonance Energy Transfer inHost–Guest Inclusion Complexes of Cyclo-dextrin–Porphyrin Composite in AqueousSolution

O

OHHO

OH

O

O

OH

HO

HNO

OOH

OH

OH

O

O

OHOH

OH

OO

OH

OH

HOO

OOH

OHHO

O

OOH

HO

HO

O

N

N N

N

ZnO

Guest

Fluorescence resonance energy transfer

1.00

0.95

0.90

0.85

0.80

0.75

0.70

ΦE

T

0.160.140.120.100.08ΦfS/τ

AN

MA

DMA

FRET efficiency vs. spectral overlapKiyotada Hosokawa, Yutaka Miura, TakayukiKiba, Toyoji Kakuchi, and Shin-ichiro Satodoi:10.1246/cl.2008.60

62 Studies of Germanium–Platinum Bonds inBis(aryl-substituted Germyl)platinum Com-plexes by Laser Flash Photolysis and Chemi-cal Trapping Experiments

Pt(Ar3Ge)2(PPhMe2)2 Ar3Geh

Ar = C6H5, p-t BuC6H4, p-Me3SiC6H4

ν

Kunio Mochida, Yusuke Masukawa, AtsukoYamada, Mai Yanaga, Masato Nanjo, HidekazuArii, Masao Gohdo, and Masanobu Wakasadoi:10.1246/cl.2008.62

64 A Homometallic Ferrimagnet Based onMixed Antiferromagnetic and Ferromag-netic Interactions through Oxamato andCarboxylato Bridges Ferromagnetic

chains

and

Antiferromaneticallycoupled

tricopper cores

Ferrimagnetic Ordering

Two novel coordination polymers, {Cu[Cu(L)(H2O)(py)]2}n (1) and {Cu[Cu(L)

oxamato-bridged tricopper units were

antiferromagnetic interaction of typical

toward ferrimagnetic ordering at 2.0 K

(MeOH)]2·2H2O}n (2), having different2-D layer structures consisting of

prepared. Compound 1 showed an

discrete tricopper complexes. Incontrast, 2 demonstrated a tendency

resulting from mixed antiferromagneticand ferromagnetic interactions throughoxamato and syn–anti-type carboxylatobridges.

Ko Yoneda, Yukari Hori, Masaaki Ohba, andSusumu Kitagawadoi:10.1246/cl.2008.64Electronic Supporting Information

66 Effect of an Asymmetrically Arranged Equa-torial Chelate Ring in an Active Site of Ni-trile Hydratase

"Asymmetric"

SS

Co

NN

OO

An effect of asymmetric chelate rings inNHase has been studied using CoIII complexwith a novel N2S2-type ligand arranged with6-5-5 chelate rings.

Takuma Yano, Yuko Wasada-Tsutsui, YujiKajita, Tomonori Shibayama, YasuhiroFunahasi, Tomohiro Ozawa, and HidekiMasudadoi:10.1246/cl.2008.66Electronic Supporting Information

68 Hybrid of Polyaniline/Iron Oxide Nanopar-ticles: Facile Preparation and CatalyticApplication H

NHNNN

n

PANI (emeraldine base)

PANI/ iron oxide nanoparticles

Fe(acac)3 +

thermal reaction

(redox catalyst)

Toru Amaya, Yumiko Nishina, Daisuke Saio,and Toshikazu Hiraodoi:10.1246/cl.2008.68Electronic Supporting Information

C-8 Chemistry Letters Vol.37, No.1 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

70 Fluorescent Tin(IV) Complexes with SchiffBase Ligands

Five novel fluorescent Schiff basetin(IV) complexes 1–5 of the type[SnCl3(L)] were synthesized andtheir properties were investigated:the emission wavelengths range

Emission spectra of 1 (), 2 (), from bluish green to orange (λ max:3 (), 4 (), and 5 (). 492–545 nm).

500 600Wavelength/nm

Nor

mal

ized

Em

issi

on

Kentaro Takano and Takashi Shibaharadoi:10.1246/cl.2008.70Electronic Supporting Information

72 Spherical Mesoporous Silica Particles withTitanium Dioxide Nanoparticles by anAerosol-assisted Coassembly

Yusuke Yamauchi, Futoshi Takeuchi, ShinichiTodoroki, Yoshio Sakka, and Satoru Inouedoi:10.1246/cl.2008.72Electronic Supporting Information

74 Highly Active and Selective Nickel–Ceri-um(IV) Oxide Catalyst for Water–Gas ShiftReaction

Ni–CeO2 catalyst prepared by coprecipitation−nitric-acid-leaching method, in which the Ni2+

ions were incorporated into CeO2 lattice and were surrounded by oxygen vacancies, was highlyactive and selective for high-temperature water–gas shift reaction in reforming.

Luhui Wang and Yuan Liudoi:10.1246/cl.2008.74

76 Controlled Photocatalytic Ability of Tita-nium Dioxide Particle by Coating with Nano-porous Silica

20 nm

(a) NPS@TiO2-L

NPS

TiO2

We have successfully deposited nanoporous silica layers

the reaction of P25 with aqueous mixture of TEOS

calcination. The thickness of nanoporous silica layer was

on titania nanoparticles, commercial P25 (Degussa), by

(silica source) and C12TAC (porogen) and the subsequent

controlled by changing the added amount of TEOS.

Risa Kato, Naoki Shimura, and Makoto Ogawadoi:10.1246/cl.2008.76

78 The Copper(II) Complex with Two DidentateSchiff Base Ligands. The Unique Rearrang-ment that Proceeds under Alcohol Vapor inthe Solid State to Construct NoninclusionStructure

A dried amorphous solid, which is a noninclusion compound prepared from an inclusioncomplex [Cu(mhsa)2]·2EtOH, does not regenerate the initial inclusion framework but yieldsa new noninclusion framework under EtOH vapor.

Yuhki Shibuya, Keiko Nabari, Mitsuru Kondo,Sachie Yasue, Kenji Maeda, Fumio Uchida,and Hiroyuki Kawaguchidoi:10.1246/cl.2008.78Electronic Supporting Information

Chemistry Letters Vol.37, No.1 (2008) C-9

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

80 Novel Derivatization Reagent, (2,4,5-Tri-methyl-3-thienyl)acetic Acid, for Electrogen-erated Tris(2,20 -bipyridine)ruthenium(III)Chemiluminescence Detection

Hitoshi Kodamatani, Yu Komatsu, ShigeoYamazaki, and Keiitsu Saitodoi:10.1246/cl.2008.80

82 Synthesis and Properties of New Tetrathia-pentalene Donors Composed of VinylogousTTFs

S

SS

SS

SS

S

R2

R2

R1

R1

1a : R1 = R2 = H 1b : R1 = R2 = SMe 1c : R1 = H, R2 = SMe

1bShintaro Iwamoto, Shunsuke Watanabe,Hiroyuki Fueno, Kazuyoshi Tanaka, and YohjiMisakidoi:10.1246/cl.2008.82Electronic Supporting Information

84 New �-Electron Donors with a 2,2,5,5-Tetra-methylpyrrolin-1-yloxyl Radical Designedfor Magnetic Molecular Conductors

New TTF and TTP donors containing a stable 2,2,5,5-tetramethylpyrrolin-1-yloxyl radicalwithin a single molecule were synthesized for the development of magnetic molecularconductors. The CV result and MO calculation suggested the possibility of the formation oftheir cation radical salts with organic radical part.

Emiko Fujiwara, Shuji Aonuma, HidekiFujiwara, Toyonari Sugimoto, and YohjiMisakidoi:10.1246/cl.2008.84Electronic Supporting Information

86 Thermally Stable Polymer Gel ElectrolytesComposed of Branched Polyimide and IonicLiquid/Zwitterion Mixture Prepared by InSitu Polycondensation

Branched polyimide was synthesized by in situ polycondensation of 4,4′-oxydianiline,

pyromellitic dianhydride, and 1,3,5-tri(4-aminophenyl)benzene in ionic liquid/zwitterionmixture.

thermally stable ion conductive materials

Polyimide gel containing ionic liquid

Ionic liquid

high thermal stabilityhigh ionic conductivity

Branched polyimide

high thermal stabilityrigid

Low compatibility

designImproved compatibility + −+

− +

+

+

+−

Masahiro Tamada, Saori Ueda, TakahiroHayashi, and Hiroyuki Ohnodoi:10.1246/cl.2008.86

88 Robustolides H and I, Chlorinated Briaranesfrom the Gorgonian Ellisella robusta (Ellisel-lidae)

O

AcO

O

OH

H

OAc

AcO

1

23

6

7

1011

12

1314

4

5

9

15

16

208

17

18

19

Cl

chair

OAcO

O

O

OH

H

OAc

AcO

Cl

OAcO

Robustolides H (1) and I (2) The ORTEP plot of robustolide I (2)showing the absolute configuration

Ping-Jyun Sung, Wei-Tse Tsai, Mei-Ru Lin,Yin-Di Su, Chen-Hao Pai, Hsu-Ming Chung,Jui-Hsin Su, and Michael Y. Chiangdoi:10.1246/cl.2008.88

C-10 Chemistry Letters Vol.37, No.1 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

90 Hydrolase-catalyzed Kinetic Resolution of5-[4-(1-Hydroxyethyl)phenyl]-10,15,20-tris-(pentafluorophenyl)porphyrin in IonicLiquids

N

HNN

NHHO

FF

FF

F

F

F

F

F

F

FF

FF

F1b

Me N N

Me

n -Bu

[bdmim][PF6]

PF6–

+

Tadashi Ema, Tokuhiro Doi, and Takashi Sakaidoi:10.1246/cl.2008.90Electronic Supporting Information

92 Clustered CpG Sequences to Enhance Cyto-kine Secretion from Macrophages

We found that the clustered

a (dA)40 tail (CpG-A) and a

murine macrophage compared

CpG ODNs, which are formedfrom the CpG ODNs containing

poly(dT), show large amountsof cytokine secretion (IL-12) in

with unclustered CpG ODNs.Jusaku Minari, Naohiko Shimada, and KazuoSakuraidoi:10.1246/cl.2008.92

94 Photochemical Site-specific Mutation of5-Methylcytosine to Thymine

Takashi Matsumura, Masayuki Ogino, KangoNagayoshi, and Kenzo Fujimotodoi:10.1246/cl.2008.94Electronic Supporting Information

96 Hexagonal BCN Films Prepared by RFPlasma-enhanced CVD

180 190 200 210 220Photon energy/eV

Inte

nsity

(ar

b un

it)

θ

75ο

55ο

0ο

B4C

h-BN

B4

B3

B2

B1

B5

NEXAFS measurement showed

the B, C, and N atoms which had

that the h-BCN layer consisted ofdifferent configurations around

the single phase of graphite-likeBCN configuration although thehexagonal structure appeared in ashort-range order.

Md. Abdul Mannan, Masamitsu Nagano, NorieHirao, and Yuji Babadoi:10.1246/cl.2008.96

98 Molecular Assembly of BChl a Complexesonto ITO Electrode Using Synthetic Light-harvesting Model Polypeptides BearingSpermine Derivative

H

Zn

++++++

++

ZnZnZnZn ZnZnZnZn

ZnZnZnZn ZnZnZnZn

BChl a

[Zn]-BChl aITO

ITO

Light-harvesting

model polypeptide

sperminederivative

e-

νe-

MV2+

h

Tsuyoshi Ochiai, Mitsuhiro Ota, TakahideAsaoka, Tomoya Kato, Shinichiro Osaka,Takehisa Dewa, Keiji Yamashita, HidekiHashimoto, and Mamoru Nangodoi:10.1246/cl.2008.98Electronic Supporting Information

Chemistry Letters Vol.37, No.1 (2008) C-11

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

100 Syntheses of Mesoporous and MicroporousMaterials via 2-Methylpentamethylenedi-amine

The hydrothermal syntheses of the high-silica microporous zeoliteZSM-48 and the mesoporous crystalline germanium oxide SU-Musing 2-methylpentamethylenediamine (MPMD) are demonstrated.

ZSM-48 SU-MStanislav Ferdov, Zhi Lin, and Rute A. SaFerreiradoi:10.1246/cl.2008.100

102 Chemical Aminoacylation of RNA by anIntermolecular Adenosine Transfer Reaction

N

N

NN

NH2

OO

O

dC rC rA rG rG rCrC rG rC rC rCrGrGrCrC-32P-5'OP-S

O-

O

dGdGdTdCdCdGdGdCdGdG-3'S

O

O

ODonor

Acceptor

dGdGdTdCdCdGdGdCdGdG-3'S

O

O

HO

dCrCrArGrGrCrCrGrCrCrCrGrGrCrC-32P-5'OPS

O-

OProduct

Transfer of adenosine derivative

OH2N

N

NN

N

NH2

OO

O

OH2N

Mingzhe Liu, Hiroshi Jinmei, Hiroshi Abe, andYoshihiro Itodoi:10.1246/cl.2008.102Electronic Supporting Information

104 Novel Nontoxic and Environment-friendlyInorganic Yellow Pigments

Representative photograph of a yellow Ce0.36Si0.31Bi0.33O1.835 pigment.

Nobuhito Imanaka, Toshiyuki Masui, andShinya Furukawadoi:10.1246/cl.2008.104Electronic Supporting Information

106 Fabrication of Octahedral Gold Nanostruc-tures Using an Alcoholic Ionic Liquid

Lanzheng Ren, Lingjie Meng, and Qinghua Ludoi:10.1246/cl.2008.106

108 Platinum-catalyzed Generation of Silylenesfrom Hydrodisilanes and Their Addition to�,�-Unsaturated Ketones

PtCl2(cod) (3 mol %)

Toluene, 40 °C, 12 h

[Pt] Si

R

R

R2 R4

O

HSiR2SiR3

R1

R3

+ R1 R4

OSiR R

R3R2

Kazuhiro Okamoto and Tamio Hayashidoi:10.1246/cl.2008.108Electronic Supporting Information

C-12 Chemistry Letters Vol.37, No.1 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

110 Synthesis, Structure, and Properties of Alka-line-earth-substituted Tungstogermanate:[K2:5(H2O)1:5]2H3[Ca2(GeW11O39)(H2O)5]2 .7H2O A novel alkaline-earth-metal-substituted

tungstogermanate derivative [K2.5(H2O)1.5]2H3

synthesized in which an infinite 2D[Ca2(GeW11O39)(H2O)5]2·7H2O has been

arrangement built up of [a-GeW11O39]8–

anions connected by calcium cation is found.α

Jingping Wang, Ruijuan Han, Xiaodi Du, andJingyang Niudoi:10.1246/cl.2008.110Electronic Supporting Information

112 Novel Synthesis of meso-Tetraarylporphy-rins by Using I2 as Catalyst and Air as Oxi-dant under Thermal or UV Conditions

NH

4

+

4 ArCHO

I2

/CH2Cl2

rt heating or UV irradiating

porphyrinogen (3) porphyrin(4)

N

HN

N

NH

Ar Ar

ArAr

HN

HN

NH

NH

Ar Ar

ArAr

(1)

(2)

air(O2)

Le Duan, Yu-Lu Wang, Xue-Sen Fan, andJin-Ye Wangdoi:10.1246/cl.2008.112Electronic Supporting Information

114 Preparation of Cellulose Nanofibers/Nano-particles via Electrospray

Cellulose Nanofibers and Nanoparticles.

Xiaofeng Sui, Jinying Yuan, Weizhong Yuan,and Mi Zhoudoi:10.1246/cl.2008.114

116 Core–Satellite Heterostruture of Fe3O4–PdNanocomposite: Selective and MagneticallyRecyclable Catalyst for DecarboxylativeCoupling Reaction in Aqueous Media

Fe3O4–Pd nanocomposite having core–satellite heterostructure, prepared through thereaction of Pluronic polymer (P123, PEO19–PPO69–PEO19)-coated Fe3O4 nanoparticle andNa2PdCl4, showed high catalytic activity, selectivity, and reusability for decarboxylativecoupling reactions in aqueous media.

Kyung Min Yeo, Sang Ick Lee, Young Tak Lee,Young Keun Chung, and In Su Leedoi:10.1246/cl.2008.116Electronic Supporting Information

118 Specific Fixed Aqueous Layer of Three-component Hybrid Liposomes Related toInhibition of Hepatoma Cells Growth

: Thickness of fixed aqueous layer (TFAL)

DMPC Tween 20

HLTFAL = 0.31 nm

THLTFAL = 0.58 nm

LactC10

Yoko Matsumoto, Yoshihiro Tanaka, KoichiGoto, and Ryuichi Ueokadoi:10.1246/cl.2008.118

Chemistry Letters Vol.37, No.1 (2008) C-13

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

120 Mixed-potential-type Zirconia-based SensorUsing In2O3 Sensing-Electrode for SelectiveDetection of Methane at High Temperature

A mixed-potential-type yttria-stabilizedzirconia (YSZ)-based sensor using In2O3

sensing electrode (SE) showed the highsensitivity as well as good selectivity toCH4 at 790 °C. The senor attached withthe 1300 °C-sintered In2O3-SE showedquicker response which was aboutfifteen times higher than that for the1400 °C-sintered In2O3-SE. -120

-90

-60

-30

0

30

60

Em

f / m

V

CO NO CH4 C3H8 C3H6

10 min

In2O3-SE (1400 °C-sintered)790 °C5 vol% H2Ogas conc.; 400 ppm eachNO; 200 ppm

Time

(a)

(b) 10 min

100

mV

400 ppmCH4

air air

(1300 °C-sintered SE)Taro Ueda, Perumal Elumalai, Vladimir V.Plashnitsa, and Norio Miuradoi:10.1246/cl.2008.120

122 Active Control of the Oxidization of a SiliconCantilever for the Characterization of Sili-con-based Semiconductors

Atsushi Ono, Kyoko Masui, Yuika Saito, TakaoSakata, Atsushi Taguchi, Masashi Motohashi,Taro Ichimura, Hidekazu Ishitobi, AlvaradoTarun, Norihiko Hayazawa, Prabhat Verma,Yasushi Inouye, and Satoshi Kawatadoi:10.1246/cl.2008.122

124 Catalytic Performance of Organically Func-tionalized Core/Shell Monodispersed Meso-porous Silica Spheres Containing an Adsorp-tion Layer

Core portion:Catalytic site

Shell portion:Adsorption/ Selective site

A new type of organically functionalized core/shellmonodispersed mesoporous silica spheres (MMSS)containing catalytic sites in the core portion andadsorption sites in the shell portion were successfullysynthesized by an expansion method.

Tomiko M. Suzuki, Tadashi Nakamura, YusukeAkimoto, and Kazuhisa Yanodoi:10.1246/cl.2008.124

Additions and Corrections

126 Stopped-flow-optical and -ESR Study on Ox-idative Reaction of Quercetin by Nitrosodi-sulfonate Radical as a Model of ReactiveOxygen Species

Hodaka Sanuki, Rushiru Komatsu-Watanabe,Tomoko Ideguchi, Shunji Sakamoto, KohjiIchimori, Kenji Kanaori, and Kunihiko Tajimadoi:10.1246/cl.2008.126