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Graphical Abstract Angew. Chem. Int. Ed. 122004

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Contents
The following articles are available online (in Wiley InterScience). You can find them at
www.angewandte.org, under Full Text, Early View.
J. Rzayev, J. Penelle*:
HP-RAFT: A Free-Radical Polymerization
Technique for Obtaining Living Polymers
of Ultrahigh Molecular Weights
DOI: 10.1002/anie.200353025
Published online: March 1, 2004
T. Kawase,* K. Tanaka, N. Shiono, Y. Seirai,
M. Oda*:
Onion-Type Complexation Based on
Carbon Nanorings and a Buckminsterfullerene
DOI: 10.1002/anie.200353517
Published online: February 27, 2004
T. S. van Erp, E. J. Meijer*:
Proton-Assisted Ethylene Hydration in
Aqueous Solution
DOI: 10.1002/anie.200353103
Published online: February 27, 2004
Articles judged by the referees or the editor as being either very important or very urgent are immediately edited, proof-read, and electronically
published once the manuscript has arrived in the editorial office in final form. As long as there is no page number available these articles should be
cited in the following manner:
Author(s) Angew. Chem. Int. Ed., online publication date, DOI.
News
Se Award to M. Verdaguer
1456
Prize for Coordination Chemistry to
A. Bousseksou
1456
Reviews 2003: Competition
Results
1456
Books
No Time to be Brief
1457
C. P. Enz
reviewed by W. Kutzelnigg
Magick, Mayhem, and Mavericks
1458
Cathy Cobb
reviewed by P. Atkins
Highlights
Catalytic Oxidation
A. Armstrong*
Some of the most promising systems
emerging for the catalytic asymmetric
epoxidation of alkenes involve the
activation of oxone (active constituent
KHSO5). The discovery of catalysis by
amines is an exciting development in this
area of organocatalysis, and a new mechanism for the activation of oxone has been
advanced with important consequences
(see scheme).
1460 – 1462
Amine-Catalyzed Epoxidation of Alkenes:
A New Mechanism for the Activation of
Oxone
Synthetic Methods
R. Kempe*
1463 – 1464
A New Arene Synthesis—Or: How Inert Is
the Cyclopentadienyl Ligand?
1446
A nice Cp recipe: The reaction of 1 with
benzonitrile is a novel arene synthesis
developed by Xi, Takahashi, and coworkers. Formally it is the breakdown of a
cyclopentadienyl ligand into a C2 fragment
and a C3 fragment which are then incorporated into a benzene and pyridine
derivative, respectively. This synthetic
variant has possible interesting applications in the preparation of oligoarenes.
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2004, 43, 1446 – 1454
Angewandte
Chemie
Reviews
Metal carboxylates form a variety of
fascinating open-framework structures
(see picture). In this Review the synthesis,
structure, and properties of various families of metal carboxylates, as well as
organic–inorganic hybrid structures
involving carboxylates, are presented. The
use of carboxylate ligands as linking
groups is of particularly interest.
Solid-State Structures
C. N. R. Rao,* S. Natarajan,
R. Vaidhyanathan
1466 – 1496
Metal Carboxylates with
Open Architectures
Communications
Completing RGB color space: The electrochemical and optical properties of the
first electrochemically prepared conducting polymer that is green in its neutral
form are reported. The extreme stability of
this polymer after 10 000 double potential
steps makes it the best and only candidate
for providing the missing third leg of RGB
color space (red, blue, and green reflection; see picture) required for polymeric
electrochromics.
Humidity-dependent electrical conductivity, which suggests possible applications
in sensors, is exhibited by OCF-6GaSe, an
open-framework gallium selenide assembled from T3 (Ga10Se2010 ) supertetrahedral clusters (picture, left). Furthermore,
materials based on T4 (Zn4Ga16Se3514 ,
right), the largest supertetrahedral selenide cluster so far, were also obtained.
For the USA and Canada:
ANGEWANDTE CHEMIE International
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Angew. Chem. Int. Ed. 2004, 43, 1446 – 1454
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Conducting Polymers
G. Sonmez, C. K. F. Shen, Y. Rubin,
F. Wudl*
1498 – 1502
A Red, Green, and Blue (RGB) Polymeric
Electrochromic Device (PECD):
The Dawning of the PECD Era
Supertetrahedral Clusters
X. Bu, N. Zheng, X. Wang, B. Wang,
P. Feng*
1502 – 1505
Three-Dimensional Frameworks of
Gallium Selenide Supertetrahedral
Clusters
individuals who are personal members of a
national chemical society, or whose institution
already subscribes, or who are retired or selfemployed consultants, print only: Europe
E 248.00/outside Europe US$ 378.00. Postage
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2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1447
Contents
Mesoporous Materials
P. R. Giunta, R. P. Washington,
T. D. Campbell, O. Steinbock,*
A. E. Stiegman*
1505 – 1507
Preparation of Mesoporous Silica
Monoliths with Ordered Arrays of
Macrochannels Templated from
Electric-Field-Oriented Hydrogels
Silica monoliths with ordered arrays of
micrometer-scale columns were fabricated from polyacrylamide gel templates.
The preparation of the template involves
the charged comonomer, N-acryloyl glycine, and is controlled by an externally
applied electric field. This approach gives
rise to the self-organization of columnar
density patterns in the template (left;
bar = 10mm) that are recovered in the
silica monoliths upon impregnation with
tetramethylorthosilicate and subsequent
calcination (right).
Microporous Materials
R. GarcLa-Zarracino,
H. HMpfl*
The hole story: A microporous material
with cavities that have an internal volume
of 1850 N3 has been formed from simple
starting materials by combining them first
through covalent coordination, and then
through hydrogen-bonding interactions.
The capsules in the 3D network can
function as hosts for guest molecules
such as triphenylmethane, sodium
tetraphenylborate, and triptycene (see
picture).
1507 – 1511
A 3D Hybrid Network Containing Large
Spherical Cavities Formed through a
Combination of Metal Coordination and
Hydrogen Bonding
Fullerenes
S. H. Kang, H. Ma, M.-S. Kang, K.-S. Kim,
A. K.-Y. Jen,* M. H. Zareie,
M. Sarikaya*
1512 – 1516
Ordered Self-Assembly and Electronic
Behavior of C60–Anthrylphenylacetylene
Hybrid
A functional hybrid molecule, C60–MPAA,
has been designed and synthesized by
taking advantage of the excellent physical
and chemical properties of C60 and nanoscale ordering of anthryl-based self-
Drug Design
More gain, less pain: A new long-acting
insulin (see structure) was created by the
enzymatic introduction of sialyllactose
into mutant insulins. The glycosylation
site was introduced into the insulin by
point mutation without loss of biological
activity. The experimental results with
mice clearly demonstrated that the introduction of a sialic acid residue is crucial in
prolonging glucose-lowering activity in
the blood.
M. Sato, R. Sadamoto, K. Niikura,
K. Monde, H. Kondo,
S.-I. Nishimura*
1516 – 1520
Site-Specific Introduction of Sialic Acid
into Insulin
1448
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
assembled monolayers (SAMs). The SAM
of C60–MPAA exhibits stable and highly
ordered 2D arrays that form an oblique
lattice at room temperature and exhibit
interesting electronic properties.
www.angewandte.org
Angew. Chem. Int. Ed. 2004, 43, 1446 – 1454
Angewandte
Chemie
Bimetallic Catalysts
L. Quebatte, R. Scopelliti,
K. Severin*
A radical alternative? Two highly efficient
catalysts for atom-transfer radical additions were discovered in a parallel
screening of bimetallic complexes. Both
Combinatorial Catalysis with Bimetallic
Complexes: Robust and Efficient Catalysts
for Atom-Transfer Radical Additions
catalysts contain a rhodium-centered
fragment (blue), which is connected
through three chloro bridges to a
ruthenium-centered fragment (red).
Molecular Switches
Switching colors: 4’,7-Dihydroxyflavylium
(AH+) in water–ionic liquid biphasic systems can be used as a write–read–erase
system. In acid media, the chalcone (Ct)
form is soluble in ionic liquids and is
thermally metastable, but reacts photochemically (write) to give the yellow
flavylium salt, which can be optically read
without being erased. The system is
prepared for a new cycle by two
consecutive pH “jumps”.
Angew. Chem. Int. Ed. 2004, 43, 1446 – 1454
1520 – 1524
F. Pina,* J. C. Lima, A. J. Parola,
C. A. M. Afonso
1525 – 1527
Thermal and Photochemical Properties of
4’,7-Dihydroxyflavylium in Water–
Ionic Liquid Biphasic Systems:
A Write–Read–Erase Molecular Switch
Dying to be seen: A series of water-soluble
and highly fluorescent perylenetetracarboxdiimides (PDIs) have been synthesized in high yields by introducing
charged groups into the bay region of PDI
(see picture; C gray, H white, S yellow, O
red). They can be used for staining living
cells as they are nontoxic.
Water-Soluble Dyes
The proof of the model is in the function:
A minimal model of hemostasis (a complex biochemical network responsible for
blood coagulation) may be implemented
with only three chemical reactions, which
creates a biomimetic functional microfluidic system that is capable of repairing
itself (as modeled in the figure). This
simple system shows threshold response
and sensitivity to flow similar to that
observed in hemostasis.
Biomimetics
www.angewandte.org
J. Qu, C. Kohl, M. Pottek,
K. Mllen*
1528 – 1531
Ionic Perylenetetracarboxdiimides:
Highly Fluorescent and Water-Soluble
Dyes for Biolabeling
M. K. Runyon, B. L. Johnson-Kerner,
R. F. Ismagilov*
1531 – 1536
Minimal Functional Model of Hemostasis
in a Biomimetic Microfluidic System
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1449
Contents
Nanostructures
N. R. Jana*
Particle anisotropy determines the way
nanoparticles self-assemble, as shown in
the picture. Gold and silver spheroids,
rods, and plates with length-to-width
ratios ranging from 1 to 25 show different
liquid-crystalline order structures. These
structures are analogous to the entropydriven ordering that occurs at high
volume fractions and is useful for largescale ordering or shape separation.
1536 – 1540
Shape Effect in Nanoparticle
Self-Assembly
Nanoparticles
A facile large-scale preparation of Pt
hollow nanospheres (see TEM image)
makes use of Co nanoparticle as sacrificial
templates. The nanospheres exhibit
enhanced electrocatalytic activity. This
method has been extended to the fabrication of industrially potentially useful Au,
Pd, and other mono- and multimetallic
hollow nanospheres.
H.-P. Liang, H.-M. Zhang, J.-S. Hu,
Y.-G. Guo, L.-J. Wan,*
C.-L. Bai*
1540 – 1543
Pt Hollow Nanospheres: Facile Synthesis
and Enhanced Electrocatalysts
Vinyl Cations
T. Mller,* M. Juhasz,
C. A. Reed*
Thermodynamic stabilization by two bsilyl substituents and essentially nonnucleophilic reaction conditions are prerequisites for the preparation of the first
structurally well-characterized vinyl cation
1 (see structure). The occurrence of
b-Si C hyperconjugation in 1 is indicated
by unusually long Si Cb bonds.
1543 – 1546
The X-ray Structure of a Vinyl Cation
Epoxidation of Propene
Direct selective gas-phase epoxidation of
propene with commercially viable conversion has been achieved with catalysts
consisting of gold nanoparticles (3–5 nm)
supported on large-pore (> 7 nm) silylated mesoporous titanosilicates with
Ba(NO3)2 as a promoter. The picture
provides a plausible mechanism for the
synergetic cooperation of the Au and Ti
sites, which is superimposed onto a TEM
image of the material.
A. K. Sinha, S. Seelan, S. Tsubota,
1546 – 1548
M. Haruta*
A Three-Dimensional Mesoporous
Titanosilicate Support for Gold
Nanoparticles: Vapor-Phase Epoxidation
of Propene with High Conversion
1450
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Angew. Chem. Int. Ed. 2004, 43, 1446 – 1454
Angewandte
Chemie
Alkane Production
G. W. Huber, R. D. Cortright,
J. A. Dumesic*
1549 – 1551
A clean stream of alkanes from renewable
biomass resources is obtained through
aqueous-phase reforming in a single
reactor. Alkanes are produced from biomass-derived sorbitol through a bifunctional pathway (see scheme) that involves
the dehydration of sorbitol on acid sites
(SiO2/Al2O3) and hydrogenation of intermediates on a metal catalyst under a H2
atmosphere. Hydrogen is produced from
sorbitol and water on the metal catalyst in
the same reactor.
Renewable Alkanes by Aqueous-Phase
Reforming of Biomass-Derived
Oxygenates
Nanotubes
Z. Chen,* S. Nagase, A. Hirsch,
R. C. Haddon, W. Thiel,
P. von R. Schleyer*
1552 – 1554
In contrast to earlier theoretical studies
and experimental expectation, full highlevel (B3LYP/6-31G*) computations on
various nanotube models reveal that
SWCNTs with O, NH, CH2, and SiH2
addends favor opened structures rather
than three-membered rings. Furthermore,
the diagonal C C bonds in (8,0) zigzag
nanotubes, rather than C C bonds parallel to the axis, are the favorable sites for
chemical modification.
Side-Wall Opening of Single-Walled
Carbon Nanotubes (SWCNTs) by
Chemical Modification: A Critical
Theoretical Study
Nanostructures
Immunoglobulin G templates: Clusters of
gold nanoparticles are grown (see picture)
from templates formed from the selfassembly of immunoglobulin Gs (IgGs)
by using a synthetic divalent antigen.
Carbohydrates inherent to IgGs create
local nucleation centers for the electroless
deposition of gold.
J. Yang,* M. Mayer, J. K. Kriebel,
P. Garstecki,
G. M. Whitesides*
1555 – 1558
Self-Assembled Aggregates of IgGs as
Templates for the Growth of Clusters of
Gold Nanoparticles
Natural Product Synthesis
J. Shimokawa, K. Shirai, A. Tanatani,
Y. Hashimoto,
K. Nagasawa*
1559 – 1562
One-step formation of an enone from a
primary alcohol has been effectively
applied in the total synthesis of batzelladine A (1). Successive 1,3-dipolar cycloadditions with a subsequent cyclization
Angew. Chem. Int. Ed. 2004, 43, 1446 – 1454
were used to form the tricyclic guanidine
subunit of this natural product, which has
the strongest inhibitory activity of HIV
gp120-CD4 binding among the batzelladines.
www.angewandte.org
Enantioselective Total Synthesis of
Batzelladine A
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1451
Contents
Drug Design
F. Agnelli, S. J. Sucheck,* K. A. Marby,
D. Rabuka, S.-L. Yao, P. S. Sears,
F.-S. Liang, C.-H. Wong*
1562 – 1566
Dimeric Aminoglycosides as Antibiotics
Double duty: Dimeric aminoglycoside
antibiotics were designed by linking neamine or nebramine cores with various
tethers differing in length and composition. The resulting dimeric aminoglycosides displayed high affinity for the 16S
A site of ribosomal RNA (a representation
of the complex is shown here) and were
effective against various aminoglycosideresistant bacterial strains.
Asymmetric Synthesis
T. Akiyama,* J. Itoh, K. Yokota,
K. Fuchibe
1566 – 1568
Enantioselective Mannich-Type Reaction
Catalyzed by a Chiral Brønsted Acid
No metal required: The Mannich-type
reaction of ketene silyl acetals 2 with
aldimines 1 proceeded highly enantioselectively to afford the syn isomer of b-
aminoesters 3 with up to 96 % ee under
the influence of a chiral Brønsted acid 4
derived from (R)-BINOL.
Going native: A highly convergent synthetic strategy was established to prepare
a skeleton structure of sperm CD52 antigen (depicted), which represents the first
chemical synthesis of a complex, all
natively linked glycosylphosphatidylinositol (GPI)–glycopeptide conjugate.
Glycopeptides
N. Shao, J. Xue, Z. Guo*
1569 – 1573
Chemical Synthesis of a Skeleton Structure of Sperm CD52—A GPI-Anchored
Glycopeptide
Computer Chemistry
L. Gagliardi,* P. PyykkM
1573 – 1576
Theoretical Search for Very Short Metal–
Actinide Bonds: NUIr and Isoelectronic
Systems
1452
Cumulated triple bonds: A new class of
molecules, the isoelectronic series of
NUIr, (depicted) has been postulated and
theoretically studied. The bond between
the actinide and the 5d-metal atom is very
short and is shown to correspond to triple
bonding. The N U bond is also a triple
bond.
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Angew. Chem. Int. Ed. 2004, 43, 1446 – 1454
Angewandte
Chemie
Catalytic Amide Synthesis
A broad range of amides is accessible in
excellent yield (> 99 %) by hydration of the
corresponding nitriles in water in the
presence of the supported ruthenium
catalyst Ru(OH)x/Al2O3 (see scheme). For
example, the industrially important con-
K. Yamaguchi, M. Matsushita,
N. Mizuno*
1576 – 1580
version of acrylonitrile into acrylamide
was achieved in quantitative yield and
better than 99 % selectivity. The catalyst
can be reused without loss of catalytic
activity and selectivity.
Efficient Hydration of Nitriles to Amides
in Water, Catalyzed by Ruthenium
Hydroxide Supported on Alumina
Bioinorganic Chemistry
A. Schmid, T. Lindel*
1581 – 1583
Modular Synthesis of Ruthenium-Labeled
Diaryl Ether Peptoids
A packet of sandwiches: A new concept of
modular assembly of novel, metal-labeled
biooligomers starting from amino acid
sandwich complexes is introduced. The
first diaryl ether tetrapeptoid containing
two ruthenium-sandwich labels is prepared (see picture; Boc = tert-butoxycarbonyl), it should now be possible to
prepare longer peptoids by repetitive
methods.
Self-Assembly
Two, three, four, or eight N-heterocycles
react in the coordination sphere of titanium(ii) compounds to give polynuclear
titanium complexes (see picture, red =
TiCp2, blue = N, white = C). Simultaneously occurring C C couplings mark a
new strategy for the synthesis of selfassembled compounds of the early transition metals.
S. Kraft, R. Beckhaus,* D. Haase,
W. Saak
1583 – 1587
Directed Reduction of Six-Membered
Nitrogen Heterocycles—Selective Formation of Polynuclear Titanium Complexes
Oxidation with Air
An additive is the key to success: Catalytic
amounts of N-methylimidazole are crucial
for the aerobic oxidation of primary aliphatic alcohols in the presence of CuCl,
1,10-phenanthroline (phen), and di-tert-
Angew. Chem. Int. Ed. 2004, 43, 1446 – 1454
butyl azodicarboxylate (DBAD). This
reaction, under neutral conditions, yields
the aldehydes quantitatively and selectively without overoxidation to the carboxylic acids.
www.angewandte.org
I. E. MarkT,* A. Gautier, R. Dumeunier,
K. Doda, F. Philippart, S. M. Brown,
C. J. Urch
1588 – 1591
Efficient, Copper-Catalyzed, Aerobic
Oxidation of Primary Alcohols
2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1453
Contents
Drug Design
On to the next round! A sensitive microarray of immobilized aminoglycosides
was used to study the binding of antibiotics to resistance-causing enzymes
(see picture). This, in combination with
other methods, will lead to the identification of new antibiotics that bind weakly to
these enzymes and strongly to the
therapeutic targets.
M. D. Disney, S. Magnet, J. S. Blanchard,
P. H. Seeberger*
1591 – 1594
Aminoglycoside Microarrays To Study
Antibiotic Resistance
Peptide Structures
C. Baldauf, R. Gnther,
H.-J. Hofmann*
1594 – 1597
Mixed Helices—A General Folding
Pattern in Homologous Peptides?
You may now exchange rings! “Mixed
helices” along a peptide sequence, in
which rings of different sizes are held
together by hydrogen bonds in alternating
directions (see picture), prove to be a
general folding principle in homologous
a-, b-, g-, and d-peptides.
Communications labeled with this symbol have been judged by two referees as being “very important papers”.
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1454
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1598 – 1599
1603
Angew. Chem. Int. Ed. 2004, 43, 1446 – 1454
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