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Chemistry Lettershttp://www.csj.jp/journals/chem-lett/
Vol.35 No.2 CMLTAGFebruary, 2006 ISSN 0366-7022
Copyright � 2006 The Chemical Society of Japan
Highlight Review
142 Heterolytic Dissociation of C–H Bond ofMethane over Agþ-exchanged Zeolites andConversion of Methane into Higher Hydro-carbons in the Presence of Ethene or Benzene
Ag+-exchanged Zeolite
ZO−Agn+ CH4
ZOδ-CH3δ+ + Agn-H
oror
CH3
ZO-H + Agn-H
H2
(ZO−: Zeolite lattice)
CC2H6 C2H4Toshihide Baba and Koji Inazu
Formation of highly polarized methoxy groups (ZO��CH3�þ) and silver hydride species (Agn–H) over Ag
þ-exchangedzeolites and reaction of the CH3
�þ with ethene and benzene form propene and toluene, respectively.
148 Chiral Symmetry Breaking in Chiral Crys-tallization and Soai Autocatalytic Reaction
N N
OH
R
N N
OH
R
N N
OH
R
N N
OH
R
SYMMETRY BREAKING
Ilya D. Gridnev
Complete chiral crystallization and absolute chiral synthesis are both fascinating phenomena shedding light on the pos-sible origins of homochirality in Nature and opening perspectives for efficient preparations of optically pure materials. Orig-inally, these two phenomena have been considered mechanistically quite different belonging to the hetero- and homogeneoussystems, respectively. However, the results of the active research in both fields undertaken in the last few years suggest thatthere may be a much closer likeness of the most important mechanistic features of these two phenomena. The present reviewbrings together the latest data on the complete chiral crystallization and absolute chiral synthesis including our own data onthe mechanism and spontaneous break of chirality in the Soai asymmetric autocatalysis.
C-20 Chemistry Letters Vol.35, No.2 (2006)
Copyright � 2006 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
Letter
154 Syntheses and Characterization of Palla-dium(II) Complexes with Tridentate N-Heterocyclic Carbene Ligands ContainingAryloxy Groups and Their Application toHeck Reaction
Cl1
O1N1 Pd1
C1
Palladium carbene complex 1
I+ +
up to TON of 135,000
Heck reaction
Takeyoshi Yagyu, Shoko Oya, MasunobuMaeda, and Koichiro Jitsukawa
156 Anomalous 13CNMR Chemical Shifts ofHigh-spin Saddle Shaped Manganese(III)Octaethyltetraphenylporphyrin Complexes N
N
N
R R
R
R
R R
R
RMn
L
L'
(a) R = Et,(b) R = H,
L = CD3ODL = CD3OD
-600-400-2000200400
δ/ppm
meso(b)
meso(a)
Akira Ikezaki, Mikio Nakamura, and Ru-JenCheng
158 An Efficient Energy Transfer Found inTriphenylene/Hexaazatriphenylene Systemwith Electronic Complimentarity and Struc-tural Similarity
N
N
NN
NN
Ar
Ar
ArAr
ArAr
N O
Ar
Ar
ArAr
ArAr
Ar =
TP-excitation HAT-emissionEN-transfer
Tsutomu Ishi-i, Hiroshi Tashiro, RempeiKuwahara, Shuntaro Mataka, ToshitadaYoshihara, and Seiji Tobita
Electronic Supporting Information
160 Effect of Fluorine Substituent on theChitinase-catalyzed Polymerization of SugarOxazoline Derivatives
-2 -1 +1 +2 +3 +4
-2 -1 +1 +2 +3 +4
Fluorinated disaccharide oxazoline derivative
Fluorinated monosaccharide oxazoline derivative
HO OHO
N
F
CH3
O
1
O OHO
N
OH
CH3
O
HO OHO
NH
F
H3CO
2O
O OHO
NH
OH
H3CO
HO OHO
NH
F
H3CO
O OHO
NH
OH
H3CO
OHO
NH
F
H3CO
chitinase from Bacillus sp.
chitinase from Bacillus sp.
No oligomers
Fluorinated chitin polymerFluorinated chitin polymerAkira Makino, Junji Sakamoto, MasashiOhmae, and Shiro Kobayashi
162 Synthesis of Single-crystal BaMo2O7 Nano-wire Bundles: A General, Low-temperatureHydrothermal Approach to 1DMolybdenumOxide-based Nanostructures
Multicomponent BaMo2O7 single-crystalline nanowire bundles were synthesized by ahydrothermal crystallization process under mild conditions using cheap and simple bulky oxideand fluoride as precursors.
Peng Gao, Yi Xie, Lina Ye, Ying Chen, andZhen Li
Electronic Supporting Information
Chemistry Letters Vol.35, No.2 (2006) C-21
Copyright � 2006 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
164 Repetitive Two-step Method for OligoareneSynthesis through Rapid Cross-couplingof Hydroxyphenylboronic Acids and Anhy-drides
OTf
rapid cross-coupling
triflation
OH
R R
OTf
R n
(HO)2BOH
OBOH
OTf
R
Shunpei Ishikawa and Kei Manabe
166 Practical One-step Synthesis of SymmetricalLiquid Crystalline Dialkyloligothiophenesfor Molecular Electronic Applications
SS
S SS
SR R
1) n-BuLi,t-BuOK
n n2) RHal
80−93%Julie Leroy, Jeremy Levin, Sergey Sergeyev,and Yves Geerts
Electronic Supporting Information
168 Synthesis and Characterization of Cyclopen-tadienone-annelated Hexadehydrodibenzo-[12]annulene
t-But-Bu
t-Bu t-Bu
O t-But-Bu
t-Bu t-Bu
O
+
Tsumoru Morimoto, Shuji Nagano, DaishiYokoyama, Masutaka Shinmen, KiyomiKakiuchi, Takashi Yoshimura, MotohiroSonoda, and Yoshito Tobe
170 Ordered CoSb3 Nanowire Arrays Synthe-sized by Electrodeposition
20 40 60 80 1000
1000
2000
3000
4000
18 21 24 270
840
420
Inte
nsi
ty/a
rb u
nit
2 /degreeθ
420
The XRD exhibits that only (420) and (840) peaks are discernible corresponding to a bccstructure with the lattice constant of a = 9.024 Å. In the experiment, we found that thesimultaneity of the nucleation, for CoSb3 nanowire, may not affect filling ratio of poresseriously and only influence the wire length.
Lijie Chen, Haining Hu, Yangxian Li, GuifengChen, Shuyun Yu, and Guangheng Wu
172 Design of Chiral Macrocyclic ComplexesBased on trans-Chelation of n:n Metal–Bidentate P,N- or N,N-Ligands N
N
O
Pri
NN
O
Pri
Pd
Cl
Cl
NN
O
Pri
NN
O
Pri
Pd
Cl
Cl
Pd PdClCl Cl
Cl>99%N
N
O
Pri
(1 equiv. each)
4 PdCl2(MeCN)2
+
Chiral self-assembled metallomacrocyclewith trans-chelation
4
28-membered ring
Manabu Hatano, Takafumi Asai, and KazuakiIshihara
Electronic Supporting Information
C-22 Chemistry Letters Vol.35, No.2 (2006)
Copyright � 2006 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
174 Platelike Crystal Growth of Zn–Al LayeredDouble Hydroxide by Hot Water Treatmentof Sol–Gel Derived Al2O3–ZnO Films onGlass Substrate
XRD patterns of Al2O3−ZnO films (Al/Zn = 1)without the hot water treatment and with thehot water treatment for 15 min.
Inte
nsity
/ ar
b. u
nit
2θ / deg. ( Cu Kα)10 50403020
(a) without hot water treatment
[003
]
[006
]
(b) with hot water treatment
We have successfully immobilized Zn−Al
30 min, and then the films were immersed in
layered double hydroxide (LDH) filmsdirectly on glass substrates through thesol−gel method with hot water treatment.Porous Al2O3−ZnO thin films were originallyprepared on glass substrates by the sol−gelmethod with a heat treatment at 400 °C for
distilled water at 100 °C for 15 min to formnanocrystalline Zn−Al LDH with hexagonalstructure.
Naoko Yamaguchi, Tomohiko Nakamura,Kiyoharu Tadanaga, Atsunori Matsuda,Tsutomu Minami, and Masahiro Tatsumisago
176 Asymmetric Addition of Alkynylzinc Re-agents to Nitrones Utilizing Tartaric AcidEster as a Chiral Auxiliary
Weilin Wei, Masato Kobayashi, Yutaka Ukaji,and Katsuhiko Inomata
178 Solution Phase Synthesis of Hollow SnO2Nanospheres at Room Temperature
Hollow SnO2 nanospheres with diameters ranging from 100–120 nm have beensynthesized via template-directed approach at room temperature. A possible formationmechanism of the hollow SnO2 nanospheres is briefly discussed.
Qinghui Cao, Yongqian Gao, Xiangying Chen,Li Mu, Weichao Yu, and Yitai Qian
Electronic Supporting Information
180 In situ Polymerization of Liquid CrystallineMonomers within Photoaligned MesoporousSilica Thin Film
Haruhiko Fukumoto, Shusaku Nagano, andTakahiro Seki
182 Hexa-, Hepta-, and Octacyclic Ladder Poly-silanes
R2Si
R2SiSiR SiR
RSi
RSi
SiR SiR
RSi
RSi
SiR
RSi
SiR
RSi
SiR SiR2
SiR2
RSiR2Si
R2SiSiR SiR
RSi
RSi
SiR SiR
RSi
RSi
SiR
RSi
SiR
RSi
SiR2
SiR2R2Si
R2SiSiR SiR
RSi
RSi
SiR SiR
RSi
RSi
SiR
RSi
SiR2
SiR2
5: R = i-Pr 6: R = i-Pr 7: R = i-Pr
Hexa-, hepta-, and octacyclic ladder polysilanes (5−7) were synthesized, and their structureswere determined by X-ray crystallography. These compounds have the double helix structureconsisting of two linear polysilane chains.
Soichiro Kyushin, Yoshinori Ueta, RyojiTanaka, and Hideyuki Matsumoto
Electronic Supporting Information
Chemistry Letters Vol.35, No.2 (2006) C-23
Copyright � 2006 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
184 Cation–�-driven Fluorescence Signalling ofAmmonium Cations by Naphthyl-substitutedZn10S16 and Cd10S16 Clusters
Zn10S16 and Cd10S16 clusters bearing twelve naphthalene units on the surface showedcharacteristic blue emission in response to the cation−π-mediated intercalative binding ofquaternary ammonium cations that allows the formation of ground-state naphthalene aggregates.
[Cd10S4(SNap)12Br4]4−
Q-ammonium ion
N++N
N+
N+N+
N+
N+
Weak Orange Emission Strong Blue EmissionKatsuaki Konishi and Takayuki Hiratani
186 Linear Relationship between Activity of aNew Ru-catalyst and Acidity of SubstitutedBenzoic Acids in the Dimerization of Acrylo-nitrile
y = −0.199x + 0.820R2 = 0.946
−0.1
−0.05
0
0.05
0.1
0.15
0.2
3.4 3.6 3.8 4.0 4.2 4.4 4.6
pKa
log(
VX
/VH
)
CNRCO2H
NCCN
NCCN
R O
OCN
NCCN
CN
2
3 4 5
Ru-based catalyst
11,4-dicyanobutene 1,4-dicyanobutane
1,4-dicyanobutadiene 2-cyanoethyl carboxylate propionitrile
A linear relationship between the activity of a ruthenium-catalyst and the acidity of m- and p-substituted benzoic acids in the dimerization of acrylonitrile was observed.
Relationship between log(VX/VH) and pKaof substituted benzoic acids
R: m- and p-X-C6H4
m-CN
m-Cl
m-MeO
p-Clm-Me
p-Me
p-MeO
o-PhCO
H
Kohichi Kashiwagi, Ryoji Sugise, ToshihiroShimakawa, Tunao Matuura, and MasashiShirai
Electronic Supporting Information
188 Stereoselective Hydrogenation of Tetralin tocis-Decalin over a Carbon-supported Rhodi-um Catalyst in Supercritical Carbon DioxideSolvent
cis-Decalin was selectivelyobtained with high cis/transratio (83%) over a carbon-supported rhodium catalyst at 333 K under 6 MPa of hydrogen and 15 MPa of carbon dioxide.
H
H
H
H
83%
17%Norihito Hiyoshi, Eiichi Mine, ChandrashekharV. Rode, Osamu Sato, and Masayuki Shirai
190 An Efficient Synthesis of Helical MesoporousSilica Nanorods
Helical mesoporous silica nanorods have been synthesized with high efficiency by simply
using primary alcohol or amine as a cosurfactant during the synthesis of MCM-41.
Qinghong Zhang, Fei Lü, Changli Li, YeWang,and Huilin Wan
192 Fabrication of Ordered Nanostructuresin Ta Films Using 2D Array of FerritinMolecules as Template
Hideki Masuda, Yoshitaka Matsui, TetsuyaMiwa, Mitsutaka Nagae, Miyuki Tanji, andKazuyuki Nishio
C-24 Chemistry Letters Vol.35, No.2 (2006)
Copyright � 2006 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
194 (Inorganic Nanofiber/Enzyme) Hybrid Hy-drogel: Preparation, Characterization, andEnzymatic Activity of Imogolite/PepsinConjugate
Pepsin
HybridHydrogel
Imogolite: natural aluminosilicate nanofiber
Al-OH groupson surface
-PO3H2 group
Nozomi Inoue, Hideyuki Otsuka, Shin-IchiroWada, and Atsushi Takahara
196 Prediction of the Octanol/Water PartitionCoefficients of Petroporphyrin Model Com-pounds
The log POW values range from 5.8 (for 1a) to 10.1 (for 2c).
N N
NNVO
N N
NNVOR
R1
R2
1a−1b 2a−2c
R
R
R
R2
R2
R2R1
R1
R1
1a: R = CH3 1b: R = C6H52a: R1 = R2 = CH3 2b: R1 = CH3, R2 = C2H5 2c: R1 = R2 = C2H5Satsuki Asami and Koichi Saitoh
198 Palladium Catalyzed Conjugate 1,4-Additionof Organoboronic Acids to �,�-UnsaturatedKetones
Addition of chloroform is essencial for catalysis.
R2
O
R1
R2
O
R1
R2
O
R1
+
Ar Ar
ArB(OH)2
CHCl3, Base
Pd(0) / Phosphine
Tetsuya Yamamoto, Michiko Iizuka, TetsuoOhta, and Yoshihiko Ito
200 Kabob-like Carbon Nanotube Hybrids SEM image of the kabob-like carbon nanotube hybrids.
Yuyang Liu, Ronghua Wang, Wei Chen,Xianqiong Chen, Zhigang Hu, Xiaoyin Cheng,and Haozhong John Xin
202 Solid Synthesis of CsxH3�xPW12O40 Saltsand Their Catalytic Activity for the Isomeri-zation of n-Butane
5 0 -5 -10 -15 -20 -25
e
d
c
b
a
ppm
CsxH3−xPW12O40 salts were prepared by asolid-synthesis method and characterized withXRD, IR, N2 sorption, and
31P MAS NMR.They exhibit comparable catalytic activityfor n-butane isomerization to that preparedvia the liquid method.
Yan Zou, Bin Yue, Bin Zhang, and Heyong He
Chemistry Letters Vol.35, No.2 (2006) C-25
Copyright � 2006 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
204 Development of Ordered Calcium CarbonateMicroarrays from Polymorph Specific Pla-nar Films
(a) (b)
(d)(c)
Ordered microarrays of rectangular
calcite, platy vaterite, and spicular
aragonite were selectively obtained
through overgrowth from planar films
prepared with polymeric species. We
successfully visualized the polymorphs
of the calcium carbonate films using the
overgrowth technique.Akiko Kotachi and Hiroaki Imai
Electronic Supporting Information
206 Liposomal Sorting onto Substrate throughIon Recognition by Gemini Peptide Lipids
Stimulus A
Tagged liposomewith gemini peptide lipid
Stimulus BMasashi Otsuki, Yoshihiro Sasaki, ShintaroIwamoto, and Jun-ichi Kikuchi
Electronic Supporting Information
208 Two-parameter Analysis of Solvent Effectson Selectivity in Chemical Reactions: Infor-mation of Polarity and Activation Volumeat the Transition State in Organic and Enzy-matic Reactions
The solvent effects on stereoselectivity (Σ) in theDiels−Alder reaction of cyclopentadiene (1), the[2 + 2]photodimerization of 2-cyclopentenone
(2), and the enzymatic asymmetrization of
prochiral 1,3-propanediols (3a−3c and 4) wereanalyzed by two-parameter treatment using both
the dielectric constant (ε) and the solubilityparameter (δ) to show a good linear relationship.
Σ = [major-isomer]/[minor-isomer]ln Σ = a[(ε − 1)/(2ε + 1)] + bδ2 + c
−1
2
3
4
1
0
ln Σ
(ob
s)
−1 10 2 3 4
Observed selectivity (ln Σ) vs calculatedselectivity (ln Σ), 1 ( ), 2 ( ), 3a ( ), 3b ( ),3c ( ), and 4 ( ).
ln Σ (calcd)
r = 0.985
Chunlei Lin, Yoshikazu Hiraga, and KatsuoOhkata
210 Protic, Imidazolium Ionic Liquids as Mediafor (Z)- to (E)-Alkene Isomerization
Ewa Janus, Marek Łożyński, and Juliusz Pernak
212 Rotaxane Synthesized by End-capping viaHydroruthenation of Axle Terminal Acety-lene and Its Derivation to �3-AllylrutheniumComplex-containing Rotaxane i) DB24C8ii) RuHCl(CO)(PPh3)3N
H2 O
PF6NH2
PF6O OO
O
OO
O
O
O
R
[Ru] Et2O
R
[Ru]
*[Ru] = RuCl(CO)(PPh3)2
R = Ph, Cy
"reactive" rotaxane
rotaxane formation
Hisahiro Sasabe, Nobuhiro Kihara, KazuhikoMizuno, Akiya Ogawa, and Toshikazu Takata
C-26 Chemistry Letters Vol.35, No.2 (2006)
Copyright � 2006 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
214 Fabrication of Gold Nanosheet and Nano-wire by Oxygen Plasma Induced Fusion ofDensely Arrayed Nanoparticles
One- and two-dimensionalfusion of densely packed goldnanoparticles was achieved byoxygen plasma treatment atroom temperature. Shin-ya Onoue, Junhui He, and Toyoki
Kunitake
Electronic Supporting Information
216 Production of COx-free Hydrogen by AlkaliEnhanced Hydrothermal Catalytic Reform-ing of Biomass-derived Alcohols COx-free hydrogen could be
produced by hydrothermalcatalytic reforming processwhen Ca(OH)2 was added intothe reaction, and biomass-derived alcohols were used asthe reactants.
Yunpeng Xu, Zhijian Tian, Guodong Wen,Zhusheng Xu, Wei Qu, and Liwu Lin
218 Fabrication of a Novel Microfluidic DeviceIncorporating 2-D Array of Microbeads
Thomas Gumpenberger, Tadatake Sato, RyozoKurosaki, Aiko Narazaki, Yoshizo Kawaguchi,and Hiroyuki Niino
220 Syntheses, Structures, and Properties ofthe First Stable 1,10-Bis(diphosphenyl)-ferrocenes
Noriyoshi Nagahora, Takahiro Sasamori, andNorihiro Tokitoh
Electronic Supporting Information
222 Bulk Synthesis of Poly(tert-butyl methacry-late) Long Macromonomer with NarrowDistribution by Atom Transfer Radical Poly-merization and Nucleophilic Substitution
1H NMR spectra of PtBMA macromonomer.
Wei Yang, Tatsuo Kaneko, Xiao-Ya Liu,Ming-Qing Chen, and Mitsuru Akashi
Electronic Supporting Information
Chemistry Letters Vol.35, No.2 (2006) C-27
Copyright � 2006 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
224 EXAFS Studies about the Sorption of Cad-mium Ions on Montmorillonite
Structural model for the Cd surface precipitate on montmorillonite.
3.39 Å3.39 Å
montmorillonite
surface precipitate
Rieko Takamatsu, Kiyotaka Asakura, Wang-Jae Chun, Tsuyoshi Miyazaki, and MasashiNakano
226 Ultrasound-promoted Highly Chemoselec-tive Reduction of Aromatic Nitro Com-pounds to the Corresponding N-Arylhydrox-ylamines Using Zinc and HCOONH4 inCH3CN
Zn/HCO2NH4,CH3CN,25-30°C
))))
NO2
R1
R2
NHOH
R1
R2Qi Xun Shi, Rong Wen Lu, Kun Jin, Zhu XiaZhang, and De Feng Zhao
Electronic Supporting Information
228 Amorphous Carbon-promoted Low-temper-ature Crystallization of Silica
Akihiro Okabe, Makiko Niki, TakanoriFukushima, and Takuzo Aida
Electronic Supporting Information
230 Photocatalytic Decomposition of Environ-mentally Persistent Perfluorooctanoic Acid
PFOA was photocatalytically decomposed by using TiO2/Ni−Cu, and a small bias potential (−0.1 V) applied on TiO2/Ni−Cu electrodegreatly enhanced its decomposition.
0
20
40
60
80
100
0 60 120 180 240 300 360Time/min
Dec
ompo
sitio
n /%
photolysisphotocatalysisphotoelectrocatalysis
Jing Chen, Pengyi Zhang, and Li Zhang
232 Importance of 30-Hydroxyl Group of theNucleosides for the Reactivity of ThymidinePhosphorylase from Escherichia coli
Thymidine phosphorylase replaced the base moiety of thymidine. We assume that this enzymerecognizes not only the base moiety but also the ribosyl hydroxyl group to fix the substrate.
Akihiko Hatano, Aiko Harano, and MasayukiKirihara
C-28 Chemistry Letters Vol.35, No.2 (2006)
Copyright � 2006 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
234 Oxygen Permeability of Surface-modifiedPoly(dimethylsiloxane) Characterized byScanning Electrochemical Microscopy
Scanning electrochemical microscopy (SECM) was employed to
quantitatively characterize the oxygen-permeation behaviors of
poly(dimethylsiloxane) (PDMS) and surface-modified PDMS by
positioning the microelectrode probe very close to sample surfaces.
The mass-transfer process of oxygen from the PDMS substrate to
the tip electrode is diffusion limited, whereas the oxygen permeability
of PDMS subjected to oxygen plasma treatment or albumin
adsorption is critically restricted. Our results suggest that PDMS-based
devices should be designed carefully since the oxygen permeability
of PDMS is possibly affected during a set of the device fabrication
procedure or cell culture within the PDMS microfluidic channels.
Hitoshi Shiku, Takeshi Saito, Ching-Chou Wu,Tomoyuki Yasukawa, Masaki Yokoo, HiroyukiAbe, Tomokazu Matsue, and Hiroshi Yamada
236 Separation of Americium(III) fromEuropium(III) by Dioctylammonium Dioc-tyldithiocarbamate/Nitrobenzene Extrac-tion
Am(III) is completely separated from Eu(III) in a neighborhood of pHeq = 6.
5 6 70
20
40
60
80
100
eq
Eu Am
%E
pH
Sunao Miyasita, Makoto Yanaga, Isamu Satoh,and Hideo Suganuma
238 Dehydrative Glycosylation in Water Using aBr�nsted Acid–Surfactant-Combined Cata-lyst
Naohiro Aoyama and Shū Kobayashi