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

Vol.42 No.2 CMLTAGFebruary, 2013 ISSN 0366-7022

Copyright © 2013 The Chemical Society of Japan

Highlight Review

94 Heterocyclic Carbene­Metal-catalyzed Csp2­Csp2 and Csp­Csp2 Couplings Using Non-metallic Substrates

HR3

R2

R4

HR2

+R1 NHC-Metalcomplex

XR1

R3

R2 R4

R1

R2or

Miguel Yus* and Isidro M. Pastor*doi:10.1246/cl.2013.94

The use of carbene ligands for transition-metal complexes has been developed in the last decades, being of special interest thosecarbenes derived from a nitrogen-containing heterocyclic system. An interesting variety of carbene­metal complexes has been testedin the Mizoroki­Heck reaction. In comparison, few examples can be found for the Matsuda­Heck version of this coupling reaction.Additionally, the Sonogashira coupling has been also catalyzed with different carbene­metal catalysts.

Letter

109 Ethyl Imidazole-1-carboxylate (EImC) as aCarbonylating Agent: Efficient Synthesis ofOxazolidin-2-ones from Amino Alcohols

OHR2

NH

R3

R1

NO

R1

R2

R3

ON

N

O

O

K2CO3 / THF

R1 = Different alkyl groupsR2 = Different alkyl (or) aryl groupsR3 = Different alkyl (or) aryl groups

S. Veeraswamy, K. Indrasena Reddy, R. VenkatRagavan,* Satyanarayana Yennam, and A.Jayashreedoi:10.1246/cl.2013.109Electronic Supporting Information

112 Synthesis of Silyl-substituted AnthraceneDerivatives via Birch-type Silylation

Li (excess)Me3SiCl (12 equiv)

THF, rt, 24 h

Me3Si

Me3Si

SiMe3

1 (30%)

DDQ (3 equiv)

toluene80 °C, 12 h

SiMe3

SiMe3

5 (89%)

SiMe3

SiMe3

SiMe3

Ken-ichiro Kanno,* Yumika Maemura, NaotakaKobayashi, and Soichiro Kyushin*doi:10.1246/cl.2013.112Electronic Supporting Information

115 Elongation of Circulation Time of a Dia-tomic Molecule Receptor in Bloodstream byAttachment to Small Gold Nanoparticles

Keiichi Karasugi, Hiroaki Kitagishi, and KojiKano*doi:10.1246/cl.2013.115Electronic Supporting Information

118 Carbon Combustion over Synthetic Potas-sium Aluminosilicate with ­LIT Structure K

Si

AlH

Without catalyst

C + O2 CO220

10

0

CO

2 fo

rmat

ion/

μmol

min

–1

900800700600500Temperature/K

–LIT type zeolite

Norihito Hiyoshi,* Takuji Ikeda, and TakakoNagasedoi:10.1246/cl.2013.118Electronic Supporting Information

121 Internally Modified Halloysite Nanotubes asInorganic Nanocontainers for a Flame Re-tardant

flame retardant(BDP)

Al

PO OO

O P OO

O

OPOO

O

Hui Jing, Yuji Higaki, Wei Ma, Hui Wu,Weng On Yah, Hideyuki Otsuka, Yuri M.Lvov, and Atsushi Takahara*doi:10.1246/cl.2013.121Electronic Supporting Information

124 Quantitative Analysis of Coke Formationduring Steam Reforming of Methane on aNickel­Hydrotalcite Catalyst under PracticalOperation Conditions

Mg-Al oxide

Ni Ni Ni Ni

Ni-incorporated hydrotalcite

CH4

Mg-Al oxide

Coke

CO2

rem

ova

l

CH4

Water vapor

Tatsuya Takeguchi,* Hiroshi Watanabe, ToruMurayama, Hiroki Takahashi, and Wataru Uedadoi:10.1246/cl.2013.124

Chemistry Letters Vol.42, No.2 (2013)C-10

http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan

127 Systematic Exploration of Lipophilic TagsThat Allow Efficient Anchoring of Aptamersto Live Cell Surfaces

Takeshi Tokunaga, Kohei Kuwahata, andShinsuke Sando*doi:10.1246/cl.2013.127Electronic Supporting Information

130 Enhanced Tumor Targeting and Photo-cytotoxicity of Folate­Poly(ethylene glycol)­Chlorin Photosensitizer Mediated by FolateReceptor

A549HeLa

Hep-20

20

40

60

80 II+FAA+F

Flu

ore

scen

ce in

ters

ity

NH N

N HN

OH

OH

OH

CONH O NHR

A R = -Boc,

I R = -Fol,

n

n =75

F = folic acidDonghong Li,* Pengxi Li, Zonglin Jiang, andLinfeng Guodoi:10.1246/cl.2013.130Electronic Supporting Information

132 Localized Sn2+ Emission Center Independ-ent of the Optical Basicity of Zinc PhosphateGlass

We have demonstrated that emission of Sn2+ center is not affected by chemical composition of the glass, indicating that local coordination state of Sn2+ emission center is generated.

Sn2+

Ca2+

Mg2+

Sr2+

Ba2+

5.04.03.02.0Energy/eV

Nor

mal

ized

inte

nsity

(ar

b un

it)Mg

BaSr

Ca

Zn

PL PLE

Hirokazu Masai,* Toshiro Tanimoto, TakumiFujiwara, SyujiMatsumoto, Yomei Tokuda, andToshinobu Yokodoi:10.1246/cl.2013.132

135 A New Method for Estimating Surface BandEnergies of a Semiconductor Electrode inContact with an Electrolyte Solution

A new graphical method is presented to estimate surface band energies (or the flat-band potential, Ufb) of a semiconductor electrode unambiguously and consistently under conditions that various kinds of surface charges exist simultaneously. Surface band energies are a key quantity for knowing the reactivity of electrons and holes in bands, and the present method will be of fundamental importance in analyzing and developing high-performance semiconductor devices such as solar cells.Yoshihiro Nakato

doi:10.1246/cl.2013.135

137 (3-Fluoro-4-methoxyanilinium)+([18]Crown-6)Supramolecular Cation Salt of Ferromag-netic [MnIICrIII(oxalate)3]¹

Toru Endo, Kazuya Kubo,* Masashi Yoshitake,Shin-ichiro Noro, Tomoyuki Akutagawa, andTakayoshi Nakamura*doi:10.1246/cl.2013.137Electronic Supporting Information

Chemistry Letters Vol.42, No.2 (2013) C-11

http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan

140 New Organic Sensitizers with N-Substitutedor Nonsubstituted Pyrrole Units for Dye-sensitized Solar Cells

hνν

NN

CN

R n

O

O

n = 1~2R = H, Me, Bu, Oct, Dod

e

02468

1012

0 0.2 0.4 0.6 0.8Cu

rren

t d

ensi

ty /

mA

cm

-2

Voltage / V

n = 1, R = Hη = 5.1%TiO2

Masaki Hara, Daisuke Kondo, TomohiroShono, Yoshihito Kunugi, and HidenoriAihara*doi:10.1246/cl.2013.140Electronic Supporting Information

143 Inclusion Crystals of 3¡,7¡,12¡,24-Tetra-hydroxycholane with Haloaromatic Com-pounds: Pitches and Stability of HerringboneAssemblies in Channels

Wen-Tzu Liu, Yute Kin, Kazunori Nakano,Ichiro Hisaki,* Norimitsu Tohnai, and MikijiMiyata*doi:10.1246/cl.2013.143Electronic Supporting Information

146 Acetals of N,N-Dimethylformamides: Ambi-philic Behavior in Converting Carbon Di-oxide to Dialkyl Carbonates

Carbon dioxide is immobilized into dialkyl carbonate using acetals of N,N-dimethylformamide under atmospheric pressure. No special treatment with tailor-made catalysts is needed. Use of dimethyl sulfoxide as a solvent is critical. An ambiphilic mechanism is proposed for the direct synthesis of dialkyl carbonates from acetals and carbon dioxide.

Yuki Takada, Aki Matsuoka, Ya Du, HiroshiNaka, and Susumu Saito*doi:10.1246/cl.2013.146Electronic Supporting Information

148 Fabricating Perovskite BaHfO3 HollowNanospheres through a Mild Reflux Route

Yongzheng Lu, Hua Huang, Tiannan Ye,Jianguo Yu, Guodong Li, and Yongnan Zhao*doi:10.1246/cl.2013.148Electronic Supporting Information

150 Low-temperature Hydrothermal Synthesis ofBismuth Nanoflowers and Their Applicationfor Heavy Metal Detection Utilizing a low-temperature hydrothermal

method, pure bismuth nanoflowers were synthesized for the first time with remarkable productivity. The obtained nanostructures were used to prepare modified electrode, which have shown high sensibility for the detection of heavy metal ions in aqueous solution by stripping analysis.

Haifeng Yang, Yan Yan,* Junfang Li, XiaojingLu, Guangcheng Xi, Qing Zhang, and ChaoWangdoi:10.1246/cl.2013.150Electronic Supporting Information

Chemistry Letters Vol.42, No.2 (2013)C-12

http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan

153 Application of Graphene as a Sorbent forPreconcentration and Determination ofTrace Amounts of Cadmium

Scanning electron micrograph of graphene packed in SPE column at 30000 magnification.

Yunkun Wang, Yanli Dong, Jingwen Zhang,Chao Li, Jingci Li,* and Jingjun Ma*doi:10.1246/cl.2013.153

156 Titration Analysis of Electron Storage andDischarge Properties of Carbon Nanodots

Carbon nanodot

e-

Oxazine 725

Methylene blue

Thionine

Methyl viologen radical

Nile blue A

e-

e- e-e-

Ken-ichi Matsuoka,* Ryo Shibuya, andKatsuhiko Fujitadoi:10.1246/cl.2013.156Electronic Supporting Information

159 A Simple Synthetic Route for the Prepara-tion of Tetramethylglycolide from LacticAcid

Kohtaro Watanabe, Yoshito Andou,* YoshihitoShirai, and Haruo Nishida*doi:10.1246/cl.2013.159Electronic Supporting Information

162 Molecular Iodine in Aqueous Ammonia:Oxidative Fragmentation of Oxiranes toNitriles

R

OI2

Aqueous ammonia

Acetonitrile, 70 °CR

CN

R= alkyl, arylYield = 70-86 %19 examples

6-7 hRavindra R. Jadhav and Krishnacharya G.Akamanchi*doi:10.1246/cl.2013.162

165 Extraordinary Microwave Effect on atropo-Enantioselective Catalytic Reduction of Bi-aryl Lactones

O

CH3

O

OH3C

CH3

O

CH3

OHM MP

H3CH3C

NB

O

H PhPh

CH3

10 mol%

in THF 30 °C

Microwave2.45 GHz

Microwaveenhancement

Dynamic Kinetic Resolution

Reaction Acceleration

BH3•THF

86% yield, 92% eeConventional:

Microwave:82% yield, 91% ee

/ 4320 min

/ 20 minKeeping high enantioselectivity!!

OH

Kazuya Nushiro, Satoshi Kikuchi, and TohruYamada*doi:10.1246/cl.2013.165Electronic Supporting Information

Chemistry Letters Vol.42, No.2 (2013) C-13

http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan

168 Production of Oxidation-resistant CopperNanoparticles on Carbon Nanotubes byPhotoreduction

Naoki Nishida, Akira Miyashita, TatsuyaTsukuda, and Hideki Tanaka*doi:10.1246/cl.2013.168Electronic Supporting Information

171 Shape-controlled Synthesis of ZnS­CuInS2­AgInS2 Solid Solution Nanoparticles andTheir Photoluminescence Properties

ZnS−CuInS2−AgInS2 (Z-CAIS) nanoparticles with rod-like or spherical shapes were successfully synthesized, the band gap of which was dependent on the chemical compositions.

Meilin Dai, Taro Uematsu, Susumu Kuwabata,and Tsukasa Torimoto*doi:10.1246/cl.2013.171Electronic Supporting Information

174 Drawing Effect of Poly(vinyl alcohol) onCrystal Growth of Calcium Carbonate

The crystal form, morphology, orientation, and nucleation frequency of the calcium carbonate thin films which were formed on poly(vinyl alcohol) (PVA) have been changed by the drawing of PVA.

VateriteAragonite VateriteAragonite

nondrawn drawn

10μ μm 25 mNaoyuki Kubo and Masafumi Yamato*doi:10.1246/cl.2013.174

177 Facile Solubilization and Photovoltaic Ap-plication of C60 Fullerene­EthylenediamineAdduct

H2N

NH2

toluene

C60PC60

toluene

C9H19COCl

C60P-DC (n)

C60-EDA adduct particle

EDA DC

P3HT (p)S

C6H13

PEDOT:PSS(hole transportlayer)

S

OO

n SO3-

n

ITO (-)

TiO2

P3HT:C60P-DC

PEDOT:PSS

Au (+)

Brown Colored Solid

nTsuyoshi Akiyama,* Taiki Ueda, Yuji Ono,Kento Kimura, Ken-ichi Matsuoka, SunaoYamada, and Takeo Okudoi:10.1246/cl.2013.177Electronic Supporting Information

180 Primary ¢-Amino Acid Salt-catalyzed Asym-metric Michael Addition of Benzoylacetatesto Cyclic Enones and Its Application for theSynthesis of Enantioenriched 1,5-Diketones

LiO2C OTBDPS

NH2

Catalyst:

Ph

O

CO2t -Bu +( )n Ph

CO2t -Bu

O

O

*( )n

O

( )n Ph

O

O

*

Catalyst

yield up to 99%ee up to 98%

CF3CO2H

Masanori Yoshida,* Ami Kubara, and ShojiHaradoi:10.1246/cl.2013.180Electronic Supporting Information

Chemistry Letters Vol.42, No.2 (2013)C-14

http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan

183 Ligand-controlled Iron-catalyzed Cross Cou-pling of Benzylic Chlorides with ArylGrignard Reagents

Cl

MgBr

Fe

PAr2

Ar2P

Cl

Cl

PAr2

Ar2Pcat. A

cat. B

71% yield

86% yield

cat. A: Ar = 4-Me2NC6H4cat. B: Ar = 3,4,5-F3C6H4

MeO

MeO

cross/homo switching

Shintaro Kawamura and Masaharu Nakamura*doi:10.1246/cl.2013.183Electronic Supporting Information

186 Synthesis of Mordenite Nanocrystals byUsing a Hydrophobic Structure-directingAgent

(b)

100 nm

(a)

100 nm

Mordenite with micron or submicron size

Mordenite nanoparticlesRelatively hydrophobicstructure-directing agent(SDA)

A common SDA withless hydrophobicity

Higher catalytic activity

N+

N+N+

Satoshi Inagaki, Yasuhiro Watanabe, YujiNishita, and Yoshihiro Kubota*doi:10.1246/cl.2013.186Electronic Supporting Information

189 Solubilization of Chemically Reduced Gra-phene Oxide Using Coffee Catechol

HO

COOHO

OH

COOH

OOH

40 °C

Coffee Coffee/GO Coffee/RGO

ChlorogenicAcid (CA)

Jang Mi Lee, Geumbi Jeong, Mi Yeon Lee,So Yeon Kim, Young Ho Park, Sung YoungPark, Sang Chun Kim,* Byung-Gak Min,* andInsik In*doi:10.1246/cl.2013.189

191 Poly(dimethylsiloxane)-protected SilverNanowire Network for Transparent Conduc-tor with Enhanced Oxidation Resistance andAdhesion Properties

Sheet resistance on UV−ozone treatment of AgNW and PDMS-protected AgNW networks.

0 100 200 300 400 0

2000

4000

6000

8000

Sh

eet

Res

ista

nce

UV-Ozone Time/min

PET

PET

AgNWPDMS(Ω

/)

Won Jin Lee, Mi Yeon Lee, Arup Kumer Roy,Kang Seok Lee, Sung Young Park,* andInsik In*doi:10.1246/cl.2013.191

194 Colorimetric Chemosensor for BariumMetal Ions Using Tris(bipyridinium­crownether) Conjugate

Haocheng Guo and Tetsuo Kuwabara*doi:10.1246/cl.2013.194

Chemistry Letters Vol.42, No.2 (2013) C-15

http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan

197 Facile Synthesis of Oligosaccharide­Poly(L-lactide) Conjugates Forming Nanoparticleswith Saccharide Core and Shell

OO

OH

n

Direct azidation

Click chemistry

+NN

Cl Cl-

OOH

HOHO

O

HOO

HOHO

O

HO

H

m

OO

OH

n

NN

NO

HOHO

O

HOO

HOHO

O

HO

H

m

Tomonari Tanaka,* Hiroyuki Fukuhara,Shin-ichiro Shoda, and Yoshiharu Kimuradoi:10.1246/cl.2013.197Electronic Supporting Information

200 Chemically Reduced Graphene Oxide withCrosslinked Shell Showing Enhanced Envi-ronmental Stability Using Thiol-graftedPluronic

HO

COOHO

OH

COOH

OOH

SH

SH

S-S S-S

GO RGO/Plu-S-S

Plu-SHSH

SHSH

O2

DTT

RGO/Plu-SH

pH

2

pH

12

eth

ano

l

pH

2

pH

12

eth

ano

l

Shell Crosslinked RGO

Geumbi Jeong, Hyun Gu Kim, Jeong A Nam,Sung Young Park,* and Insik In*doi:10.1246/cl.2013.200

Chemistry Letters Vol.42, No.2 (2013)C-16

http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan