Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(42), P. 9079 - 9084
Published: Oct. 15, 2024
We
report
a
novel
halogen-bond-assisted
NHC-catalyzed
(dynamic)
kinetic
resolution
strategy
for
the
synthesis
of
axially
chiral
heterobiaryls.
A
class
quinolines
are
prepared
efficiently
in
excellent
enantioselectivities
(≤98%
ee)
employing
3-5
mol
%
NHC
catalyst.
Mechanistic
studies
reveal
indispensability
5-bromo-2-iodobenzaldehyde
this
reaction,
which
pivotal
halogen
bonding
interaction
plays
crucial
role
process.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(31)
Published: May 11, 2024
The
use
of
noncovalent
interactions
based
on
electrophilic
halogen,
chalcogen,
pnictogen,
or
tetrel
centers
in
organocatalysis
has
gained
noticeable
attention.
Herein,
we
provide
an
overview
the
most
important
developments
last
years
with
a
clear
focus
experimental
studies
and
catalysts
which
act
via
such
non-transient
interactions.
Helvetica Chimica Acta,
Journal Year:
2024,
Volume and Issue:
107(5)
Published: March 6, 2024
Abstract
It
is
often
said
that
pnictogen‐bonding
catalysis,
and
σ
‐hole
catalysis
in
general,
would
not
work
aqueous
systems
because
the
solvent
interfere
as
an
overcompetitive
pnictogen‐bond
acceptor.
In
this
study,
we
show
transfer
of
from
hydrophobic
solvents
to
possible
by
replacing
only
with
hydrophilic
substrates,
without
changing
catalyst
or
reaction.
This
differs
conventional
covalent
Lewis
acid
catalysts,
which
are
instantaneously
destroyed
ligand
exchange.
With
their
water‐proof
substituents
place
exchangeable
ligands,
supramolecular
counterpart
evinced
catalyze
hydrogenation
quinolines
neutral
systems.
To
secure
these
results,
introduce
a
water‐soluble
fluorogenic
substrate
releases
coumarin
upon
reduction
instead
activated
quinolidiniums,
stiborane
catalysts
deepened
holes.
They
demonstrate
can
operate
higher‐order
architectures
for
under
biologically
relevant
conditions,
provide
operational
assay
high‐throughput
screening
fluorescence
imaging,
situ
conditions.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(45)
Published: July 5, 2024
Abstract
The
objective
of
this
study
was
to
create
artificial
enzymes
that
capitalize
on
pnictogen
bonding,
a
σ‐hole
interaction
is
essentially
absent
in
biocatalysis.
For
purpose,
stibine
catalysts
were
equipped
with
biotin
derivative
and
combined
streptavidin
mutants
identify
an
efficient
transfer
hydrogenation
catalyst
for
the
reduction
fluorogenic
quinoline
substrate.
Increased
catalytic
activity
from
wild‐type
best
coincides
depth
σ
hole
Sb(V)
center,
emergence
saturation
kinetic
behavior.
Michaelis–Menten
analysis
reveals
transition‐state
recognition
low
micromolar
range,
more
than
three
orders
magnitude
stronger
millimolar
substrate
recognition.
Carboxylates
preferred
by
contribute
hydrogen‐bonded
ion
pairing
anion‐π
interactions
emerging
pyridinium
product.
challenging
stereoselectivity
aqueous
systems
further
emphasizes
compatibility
bonding
higher
order
catalysis.
Journal of the Mexican Chemical Society,
Journal Year:
2025,
Volume and Issue:
69(1), P. 185 - 258
Published: Jan. 1, 2025
Almost
two
centuries
have
passed
since
Strecker
synthesized
for
the
first
time
α-aminoacid
DL-alanine
via
a
sequential
combination
of
acetaldehyde
with
aqueous
ammonia
and
hydrogen
cyanide,
coupled
to
further
hydrolysis
resulting
α-aminonitrile
using
an
acid
solution.
Since
then,
broad
variety
high
valued
products
in
various
fields
science
technology
been
three-component
reactions
(3CRs)
or
one-pot
methodologies
involving
3CRs
smartly
processes
like
functionalizations,
condensations,
cross
couplings,
cyclizations,
ring
openings,
so
on.
In
same
way,
very
interesting
useful
computational
calculations
behind
understanding
reaction
mechanisms
related
3CRs,
conformational
analyses,
energy
profiles
performed.
All
these
topics
are
on
scope
present
review,
which
covers
selected
elegant
based
(except
Ugi-3CR
its
variants),
other
unclassified
3CR-based
works
from
2010
nowadays.
Resumen.
Han
pasado
casi
dos
siglos
desde
que
sintetizó
por
primera
vez
el
α-aminoácido
DL-alanina
mediante
una
combinación
secuencial
de
acetaldehído
con
amoníaco
acuoso
y
cianuro
hidrógeno,
acoplada
hidrólisis
posterior
del
α-aminonitrilo
resultante
utilizando
solución
acuosa
ácida.
Desde
entonces,
se
ha
sintetizado
amplia
variedad
productos
gran
valor
en
diversos
campos
la
ciencia
tecnología
reacciones
tres
componentes
(3CR)
o
metodologías
un
mismo
reactor
implican
3CR
acopladas
procesos
posteriores
como
funcionalizaciones,
condensaciones,
acoplamientos
cruzados,
ciclizaciones,
aperturas
anillos,
etc.
Del
modo,
han
realizado
cálculos
computacionales
muy
interesantes
útiles
para
comprender
los
mecanismos
reacción
relacionados
3CR,
análisis
conformacionales
perfiles
energéticos.
Todos
estos
temas
están
dentro
alcance
presente
artículo
revisión,
considera
trabajos
seleccionados
elegantes
basados
(excepto
sus
variantes),
otras
no
clasificadas
hasta
actualidad.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 3, 2025
Halogen
bonding
has
been
established
as
a
promising
tool
in
organocatalysis.
Asymmetric
processes
are
nevertheless
scarce,
and
their
applications
limited
to
few
studies
applying
chiral
halogen
bond
donors.
Herein,
we
combine
with
asymmetric
counteranion-directed
catalysis,
providing
the
first
highly
enantioselective
example
of
such
an
approach.
A
strong
bidentate
iodine(III)-based
catalyst
disulfonimides
counteranions
is
applied
organocatalysis
Diels-Alder
reaction
between
cyclopentadiene
trans-β-nitrostyrene,
key
step
synthesis
drug
fencamfamine,
which
was
prepared
high
enantioselectivity.
Beilstein Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
21, P. 547 - 555
Published: March 12, 2025
β-Amino
cyanoesters
are
important
scaffolds
because
they
can
be
transformed
into
useful
chiral
amines,
amino
acids,
and
alcohols.
Halogen
bonding,
which
formed
between
halogen
atoms
electron-rich
chemical
species,
is
attractive
of
its
unique
interaction
in
organic
synthesis.
Chiral
halonium
salts
have
been
found
to
strong
halogen-bonding-donor
abilities
work
as
powerful
asymmetric
catalysts.
Recently,
we
developed
binaphthyl-based
applied
them
several
enantioselective
reactions,
the
corresponding
products
high
excellent
enantioselectivities.
In
this
paper,
synthesis
β-amino
with
contiguous
tetrasubstituted
carbon
stereogenic
centers
by
Mannich
reaction
through
salt
catalysis
presented,
provided
yields
up
86%
ee.
To
best
our
knowledge,
present
paper
first
report
construction
catalytic
reaction.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(20), P. 5938 - 5984
Published: Jan. 1, 2024
This
review
summarises
methods
to
synthesise
and
apply
fluorine-
polyfluoroalkyl/aryl-substituted
1,2,3-triazoles.
Focus
is
devoted
recent
examples
those
where
the
properties
of
both
1,2,3-triazole
fluorine
groups
are
important.
