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Graphical Abstract Angew. Chem. Int. Ed. 422003

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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.
N. Guillou,* C. Livage, M. Drillon, G. Frey:
The Chirality, Porosity, and Ferromagnetism of a 3D Nickel Glutarate with Intersecting 20-Membered Ring Channels
DOI: 10.1002/anie.200352520
Published online: October 20, 2003
F. R. Harris, S. Standridge, C. Feik,
D. C. Johnson*:
Design and Synthesis of [(Bi2Te3)x(TiTe2)y]
Superlattices
DOI: 10.1002/anie.200351724
Published online: October 22, 2003
M. K)hn, R. Wacker, C. Peters, H. Schr)der,
L. Soulere, R. Breinbauer,* C. M. Niemeyer,*
H. Waldmann*:
Staudinger Ligation: A New Immobilization Strategy for the Preparation of SmallMolecule Arrays
DOI: 10.1002/anie.200352877
Published online: October 20, 2003
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
Nobel Prizes 2003: Magnetic-Resonance Imaging; Superconductors and -fluids; Ion Channels
5116
Books
Industrial Guide to Chemical and Drug
Safety
5117
T. S. S. Dikshith, Prakash V. Diwan
reviewed by B. Stock
Photochemical Purification of Water and
Air
5117
Thomas Oppenl-nder
reviewed by A. M. Braun
Highlights
Ni-Catalyzed Coupling Reactions
S.-i. Ikeda*
5120 ? 5122
Nickel-Catalyzed Coupling of Carbonyl
Compounds and Alkynes or 1,3-Dienes:
An Efficient Method for the Preparation of
Allylic, Homoallylic, and Bishomoallylic
Alcohols
5106
Nickel-catalyzed multicomponent
coupling of carbonyl compounds with
alkynes or 1,3-dienes and organometallic
reagents represents an efficient route to
allylic, homoallylic, and bishomoallylic
alcohols with good regio-, stereo-, and
enantioselectivity. The reaction proceeds
via the nickelacycle species I or I? (see
scheme), and not by the usual alkenylation, allylation, and homoallylation of
carbonyl compounds.
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2003, 42, 5106 ? 5112
Angewandte
Chemie
Minireviews
Lamellar inorganic compounds, in
analogy with the graphitic form of carbon,
are susceptible to folding forces that can
lead them to adopt fullerene-like or nanotubular structures. The development of
inorganic nanomaterials (such as the
assembly of the single-wall MoS2 nanotubes shown) has now reached the stage
where many important applications in
catalysis, lubrication, and nanotechnology
are within reach.
Fullerene-Like Nanomaterials
R. Tenne*
5124 ? 5132
Advances in the Synthesis of Inorganic
Nanotubes and Fullerene-Like
Nanoparticles
Reviews
Porphyrin Chemistry
As the name implies: Expanded porphyrins, that is, larger, extended porphyrin
derivatives (example shown), are fascinating synthetic additions to the world of
natural tetrapyrrolic pigments. Their
structural aesthetics, theoretical interest,
and potential practical utility have
resulted in a rapid blossoming of this
field. This Review provides an overview of
the latest developments, with a focus on
preparative chemistry.
J. L. Sessler,* D. Seidel
5134 ? 5175
Synthetic Expanded Porphyrin Chemistry
Communications
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Angew. Chem. Int. Ed. 2003, 42, 5106 ? 5112
One hand is better than two! Chirality
transfer from the single molecule into a
two-dimensional layer is investigated by
STM. The supramolecular handedness in
homochiral heptahelicene layers, generated on a single-crystal surface (see
picture), results from the orientations of
next-neighbor molecules. The intermolecular interaction is dominated by steric
repulsive forces between the rigid helices,
causing a direct transfer of chirality.
Chirality
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www.angewandte.org
R. Fasel,* M. Parschau,
K.-H. Ernst*
5178 ? 5181
Chirality Transfer from Single Molecules
into Self-Assembled Monolayers
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5107
Contents
Molecular Gears
Molecular flippers: The Ag3L2 complexes,
which are quantitatively formed from two
disk-shaped tridentate ligands (thiazolylor pyridyl-based) and three Ag+ ions, are
helical and twist between the P and M
forms (see scheme). The flip motion
includes a relative 1208 rotation between
the two disk-shaped ligands connected by
the Ag+ ions.
S. Hiraoka, K. Harano, T. Tanaka, M. Shiro,
M. Shionoya*
5182 ? 5185
Quantitative Formation of SandwichShaped Trinuclear Silver(i) Complexes
and Dynamic Nature of Their P蠱 Flip
Motion in Solution
Cyclic Glycopeptides
Blocking flu: A cyclic peptide, cyclo(SerGly-Gly-Gln-Ser-His-Asp)3, is an excellent
scaffold for the synthesis of a cyclic
glycopeptide carrying GM3 oligosaccharides with a potent inhibitory effect on the
hemagglutination induced by the influenza virus. Tridentate binding of the
gylcopeptide is shown to produce a much
greater inhibitory effect than di- or monodentate binding. The shape of the
glycopeptide protein scaffold, which is
determined by the amino acid sequence
employed, is also found to be significant
in determining the inhibitory activity.
T. Ohta, N. Miura, N. Fujitani,
F. Nakajima, K. Niikura, R. Sadamoto,
C.-T. Guo, T. Suzuki, Y. Suzuki,
K. Monde, S.-I. Nishimura* 5186 ? 5189
Glycotentacles: Synthesis of Cyclic
Glycopeptides, Toward a Tailored Blocker
of Influenza Virus Hemagglutinin
Linker-Controlled Aggregation
Y. Saiki, K. Nakamura, Y. Nigorikawa,
M. Yamaguchi*
5190 ? 5192
[3�Cycloalkyne Oligomers: Linking
Groups Control Intra- and Intermolecular
Aggregation by p?p Interactions
Molecules get together: Two dimeric and
a trimeric [3�cycloalkyne (see picture)
are synthesized, and their aggregation
behavior in CHCl3 examined by 1H NMR
spectroscopy, circular dichroism, and
vapor pressure osmometry. The aggregate
structure of the oligomeric [3�cycloalkynes can be controlled by the structures
of the linker moiety.
Biomineralization
M. Sumper,* S. Lorenz,
E. Brunner
Diatom shells (see picture of cell of
Stephanopyxis turris) contain long-chain
polyamines attached either to putrescine
or to phosphorylated silaffin peptides.
These polyamines direct the in vitro formation of silica nanospheres from silicic
acid. The concentration of multivalent
anions (such as phosphate) defines the
diameter of the nanospheres produced.
5192 ? 5195
Biomimetic Control of Size in the
Polyamine-Directed Formation of
Silica Nanospheres
5108
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2003, 42, 5106 ? 5112
Angewandte
Chemie
Syngas Production
Two processes in one space: Methane, the
main component of natural gas, can be
converted into syngas efficiently in a twostage oxygen-permeable ceramic membrane reactor by means of integrated
oxidation and reforming processes (see
picture). This could be a cheaper alternative to the current steam-reforming of
methane.
C.-s. Chen,* S.-j. Feng, S. Ran, D.-c. Zhu,
W. Liu,
H. J. M. Bouwmeester
5196 ? 5198
Conversion of Methane to Syngas by a
Membrane-Based Oxidation?Reforming
Process
Glycal Cyclization
A new class of carbohydrate analogues,
benzo-fused heterobicycles 1, can be
prepared by cyclization of d-glucals with
aryl amines in the presence of 10 mol %
indium tribromide under mild and con-
venient reaction conditions [Eq. (1)]. The
structure and configuration of the products were established by extensive NMR
experiments and molecular modeling
studies.
J. S. Yadav,* B. V. S. Reddy, K. V. Rao,
K. Saritha Raj, A. R. Prasad,
S. Kiran Kumar,
A. C. Kunwar, P. Jayaprakash,
B. Jagannath
5198 ? 5201
InBr3-Catalyzed Cyclization of Glycals with
Aryl Amines
Group 11 Hydrides
Coinage metal hydrides are stabilized by
negative charge: Reactions of energized
laser-ablated gold, silver, and copper with
H2 in excess argon, neon, and pure
normal hydrogen during condensation at
3.5 K give the MH molecules, the (H2)MH
complexes, the MH2 ions, and the MH4
ion only for gold. The stable linear MH2
ions are unique in that their corresponding neutral MH2 molecules are higher in
energy and thus unstable to M + H2
decomposition.
X. Wang, L. Andrews*
5201 ? 5206
Gold Is Noble but Gold Hydride Anions
Are Stable
Matrix Generation of C3N4
T. Sato,* A. Narazaki, Y. Kawaguchi,
H. Niino, G. Bucher
5206 ? 5209
Carbon nitride molecules: Photolysis
(l = 266 nm) of triazido-s-triazine (C3N12,
1) in a nitrogen matrix at 20 K yielded a
succession of reactive species (see
Angew. Chem. Int. Ed. 2003, 42, 5106 ? 5112
scheme), including, in order, an apparent
trinitrene, NCN, and a novel C3N4 isomer,
dicyanocarbodiimide NCN糃糔CN.
www.angewandte.org
Dicyanocarbodiimide and Trinitreno-s-triazine Generated by Consecutive
Photolysis of Triazido-s-triazine in a
Low-Temperature Nitrogen Matrix
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5109
Contents
Stereoselective C-Sialylation
Z. Abdallah, G. Doisneau,
J.-M. Beau*
5209 ? 5212
Synthesis of a Carbon-Linked Mimic of the
Disaccharide Component of the TumorRelated SialylTn Antigen
The right mix! When one considers the
many ways in which a polyfunctional
organometallic species may be quenched
before any productive CC bond formation can occur (two amide protons, five
esters), the samarium-promoted coupling
Self-Assembly of Cobalt Nanorods
between sulfide 1 and aldehyde 2 is
remarkably efficient (see scheme). This is
shown in the synthesis of a stable mimic
of the sialylTn (Tn = GalNAca1!O-Ser/
Thr) disaccharide.
Coalescence of initially produced nanospheres inside 3D super-lattices may be
the reason for the formation of ferromagnetic cobalt nanorods, monodisperse in
length and diameter, from [Co(h3C8H13)(h4-C8H12)] in the presence of stearic acid and hexadecylamine. The selforganization of these nanorods into
unprecedented hexagonal 2D and 3D
super-lattices has been studied by transmission electron microscopy (see
picture).
F. Dumestre, B. Chaudret,* C. Amiens,
M. Respaud, P. Fejes, P. Renaud,
P. Zurcher
5213 ? 5216
Unprecedented Crystalline Super-Lattices
of Monodisperse Cobalt Nanorods
Difluoromethylenation
G. K. S. Prakash,* J. Hu, T. Mathew,
G. A. Olah
5216 ? 5219
Difluoromethyl Phenyl Sulfone as a
Selective Difluoromethylene Dianion
Equivalent: One-Pot Stereoselective Synthesis of anti-2,2-Difluoropropane-1,3diols
Intramolecular charge?charge repulsion
rather than traditional steric control is
responsible for the high diastereoselectivity (up to 94 % de) obtained in tBuOKinduced difluoromethylenation of alde-
hydes 1 with difluoromethyl phenyl sulfone (2) to give symmetrical and unsymmetrical anti-2,2-difluoropropane-1,3diols 3.
Rational outer-sphere design can be used
to optimize heterogeneous catalysts.
Thus, imprinting of bulk silica was used to
prepare tethered active sites with hydrophilic (1) and hydrophobic environments
(2). In the Knoevenagel condensation of
isophthalaldehyde with malonitrile, for
example, 1 gave rate enhancements of
about 50 and 30 relative to 2 and a
commercial catalyst consisting of a monolayer of 3-aminopropyl groups on silica,
respectively.
Optimizing Heterogeneous Catalysts
J. D. Bass, S. L. Anderson,
A. Katz*
5219 ? 5222
The Effect of Outer-Sphere Acidity on
Chemical Reactivity in a Synthetic
Heterogeneous Base Catalyst
5110
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2003, 42, 5106 ? 5112
Angewandte
Chemie
s-Bond Metathesis
I. L. Fedushkin,* N. M. Khvoinova,
A. A. Skatova, G. K. Fukin
5223 ? 5226
The use of a rigid bidentate ligand allows
oxidative addition of an acetylene derivative to a non-transition-metal complex,
not through oxidation of the metal atom,
Oxidative Addition of Phenylacetylene
through CH Bond Cleavage To Form the
Mgii?dpp-bian Complex: Molecular Structure of [Mg{dpp-bian(H)}(CCPh)(thf)2]
and Its Diphenylketone Insertion Product
[Mg(dpp-bian)C{OC(Ph2)CCPh}(thf)]
but through s-bond metathesis from
ML: and HC to form HL贩稭C
(see scheme; Ar = 2,6-iPr2C6H3).
The abstraction reaction H + CD4 !CD3
+ HD is studied at a collision energy of
~ 2 eV under single-collision conditions
(see picture). Most of the available energy
appears in product translational motion,
and the CD3 product is scattered sideways
and backward with respect to the incident
H-atom direction. This behavior is unexpected based on simple atom?diatom
models.
Reaction Dynamics at a C Atom
J. P. Camden, H. A. Bechtel,
R. N. Zare*
5227 ? 5230
Dynamics of the Simplest Reaction of a
Carbon Atom in a Tetrahedral
Environment
A Macrosphelide Library
T. Takahashi,* S.-i. Kusaka, T. Doi,
T. Sunazuka, and S. O?mura 5230 ? 5234
A Combinatorial Synthesis of a
Macrosphelide Library Utilizing a
Palladium-Catalyzed Carbonylation on
a Polymer Support
Supported total synthesis: The combinatorial synthesis of a 122-membered macrosphelide library including macrosphelides A, C, E, and F (see picture) has been
achieved based on a unique strategy for a
three-component coupling utilizing a palladium-catalyzed chemoselective carbonylation and an unprecedented macrolactonization on a polymer support.
Binding Assays with Native Markers
G. HQfner, K. T. Wanner*
MS makes it possible: Competitive binding assays are a widely used tool in drug
research to characterize the affinity of a
ligand for a biological target. However,
these assays generally require special
ligands which can be detected with high
sensitivity, such as radioligands or ligands
Angew. Chem. Int. Ed. 2003, 42, 5106 ? 5112
coupled to a fluorophore. Now native
markers may be employed in conjunction
with mass spectrometric quantification.
First studies demonstrate this approach
in binding experiments at dopamine
D1-receptors.
www.angewandte.org
5235 ? 5237
Competitive Binding Assays Made Easy
with a Native Marker and Mass
Spectrometric Quantification
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5111
Contents
Carotenoid Aggregates
B. J. Foss, S. N. N鎠s, H.-R. Sliwka,*
V. Partali
5237 ? 5240
Stable and Highly Water-Dispersible,
Highly Unsaturated Carotenoid
Phospholipids?Surface Properties and
Aggregate Size
No additives are required for the study of
hydrophobic carotenoids in aqueous solutions, if these compounds are present as
highly unsaturated phospholipids (see
Alkene Hydrogenation
structure). These compounds form small,
highly water-dispersible carotenoid
aggregates.
Size matters: Under low-pressure conditions, hydrogenation of alkenes, such as
2-pentene and ethene, is shown to occur
on supported palladium nanoparticles,
whereas single-crystal palladium surfaces
are inactive. This finding is rationalized on
the basis of the accessibility of weakly
bound subsurface hydrogen (see picture),
which is enhanced on particles of nanometer dimensions.
A. M. Doyle, Sh. K. Shaikhutdinov,*
D. Jackson, H.-J. Freund
5240 ? 5243
Hydrogenation on Metal Surfaces:
Why are Nanoparticles More Active than
Single Crystals?
Stable N-Heterocyclic Carbenes
F. E. Hahn,* M. Paas, D. Le Van,
T. LVgger
5243 ? 5246
Simple Access to Unsymmetrically
Substituted, Saturated N-Heterocyclic
Carbenes
Secondary amines and imines were used
to prepare unsymmetrically substituted,
non-aromatic N-heterocyclic carbenes via
imidazolidine-2-thiones (rac-1) as inter-
mediates. The presence of only one sterically demanding substituent on one of the
N atoms in rac-2 is sufficient to prevent
dimerization to the enetetramine.
Communications labeled with this symbol have been judged by two referees as being ?very important papers?.
The publication of Communications labeled with this symbol has been accelerated because of their topical or highly competitive
nature.
Service
5112
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Keywords
5248
Authors
5249
Preview
5251
Angew. Chem. Int. Ed. 2003, 42, 5106 ? 5112
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