Angewandte Chemie,
Journal Year:
2022,
Volume and Issue:
134(42)
Published: July 25, 2022
Abstract
Die
weite
Verbreitung
von
C
‐Arylglykosiden
in
biologisch
aktiven
Naturstoffen
und
zugelassenen
Arzneimitteln
hat
seit
langem
zur
Entwicklung
effizienter
Strategien
für
ihre
selektive
Synthese
motiviert.
Kreuzkupplungen
wurden
häufig
verwendet,
waren
aber
größtenteils
auf
Palladiumkatalysatoren
vorfunktionalisierten
Substraten
angewiesen,
während
sich
die
Ruthenium‐katalysierte
Herstellung
bisher
als
schwer
zugänglich
erwiesen
hat.
Wir
stellen
hier
eine
vielseitige
Ruthenium(II)‐katalysierte
meta
‐C−H‐Glykosylierung
vor,
um
‐
‐Arylglykoside
aus
leicht
verfügbaren
Glykosylhalogenid‐Donoren
zu
gewinnen.
Robustheit
der
Ruthenium‐Katalyse
zeigte
milden
Reaktionsbedingungen,
hervorragender
anomerer
Selektivität
ausschließlicher
‐Selektivität.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(26)
Published: April 22, 2023
Twofold
distal
C-H
functionalization
was
accomplished
by
difunctionalization
of
nonactivated
alkenes
to
provide
rapid
access
multifunctionalized
molecules.
The
multicomponent
ruthenium-catalyzed
remote
1,n-difunctionalization
(n=6,7)
with
fluoroalkyl
halides
and
heteroarenes
in
a
modular
manner
is
reported.
meta-C(sp2
)-H/C-6(sp3
)-H
featured
mild
conditions,
unique
selectivity,
broad
substrate
scope
domino
process
for
twofold
C(sp2
)-H/C(sp3
activation
the
sequential
formation
three
different
carbon-centered
radicals.
A
plausible
mechanism
proposed
based
on
detailed
experimental
computational
studies.
ChemSusChem,
Journal Year:
2023,
Volume and Issue:
16(12)
Published: March 7, 2023
Electrochemically
promoted
transition
metal-catalyzed
C-H
functionalization
has
emerged
as
a
promising
area
of
research
over
the
last
few
decades.
However,
development
in
this
field
is
still
at
an
early
stage
compared
to
traditional
reactions
using
chemical-based
oxidizing
agents.
Recent
reports
have
shown
increased
attention
on
electrochemically
functionalization.
From
standpoint
sustainability,
environmental
friendliness,
and
cost
effectiveness,
oxidation
metal
catalyst
offers
mild,
efficient,
atom-economical
alternative
chemical
oxidants.
This
Review
discusses
advances
metal-electrocatalyzed
past
decade
describes
how
unique
features
electricity
enable
economic
sustainable
way.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 12, 2024
An
efficient
approach
for
the
remote
C-H
alkylation
of
arenes,
employing
a
variety
N-directing
groups
is
described.
This
method
facilitates
straightforward
synthesis
valuable
phenylethylamine
derivatives
by
exclusively
cleaving
benzylic
C-N
bond
in
aziridines.
Furthermore,
these
products
can
easily
remove
protecting
groups,
resulting
meta-substituted
compounds,
such
as
amines
and
ketones,
which
hold
significance
synthetic
chemistry.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(19), P. 7353 - 7358
Published: Sept. 14, 2021
Herein,
we
present
m-C–H
olefination
on
derivatives
of
phenylacetic
acids
by
tethering
with
a
simple
nitrile-based
template
through
palladium
catalysis.
Notably,
the
versatility
method
is
evaluated
wide
range
acid
for
obtaining
meta-olefination
products
in
fair
to
excellent
yields
outstanding
selectivities
under
mild
conditions.
Significantly,
strategy
successfully
exemplified
synthesis
drugs/natural
product
analogues
(naproxen,
ibuprofen,
paracetamol,
and
cholesterol).
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(12), P. 2376 - 2380
Published: March 23, 2022
Herein,
we
describe
a
nickel-catalyzed
reductive
deaminative
arylalkylation
of
tethered
alkenes
with
pyridinium
salts
as
C(sp3)
electrophiles.
This
two-component
dicarbofunctionalization
reaction
enables
the
efficient
synthesis
various
benzene-fused
cyclic
compounds
bearing
all-carbon
quaternary
centers.
The
approach
presented
in
this
paper
proceeds
under
mild
conditions,
tolerating
wide
variety
functional
groups
and
heterocycles.
It
has
been
used
to
functionalize
complicated
molecules
at
late
stage.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(44)
Published: May 23, 2023
A
ruthenium-catalyzed
para-selective
alkylation
of
protected
anilines
to
construct
α-arylacetonitrile
skeletons
has
been
reported.
We
firstly
disclosed
the
ethyl
2-bromo-2-cyanopropanoate
was
an
effective
alkylating
reagent
in
ruthenmuim-catalyzed
remote-selective
C-H
functionalization.
wide
variety
can
be
directly
obtained
with
moderate
good
yields.
Importantly,
products
contain
both
nitrile
and
ester
groups
guaranteeing
its
direct
transformation
into
other
useful
synthetic
units,
indicating
importance
this
method.
Angewandte Chemie,
Journal Year:
2022,
Volume and Issue:
134(32)
Published: June 8, 2022
Abstract
C‐aryl
glycosides
are
popular
basic
skeletons
in
biochemistry
and
pharmaceutical
chemistry.
Herein,
ruthenium‐catalyzed
highly
stereo‐
site‐selective
ortho
‐
meta
‐C
Ar
−H
glycosylation
is
described.
A
series
of
pyranosides
furanosides
were
synthesized
by
this
method.
The
strategy
showed
good
substrate
scope,
various
N
‐heterocyclic
directing
groups
compatible
with
the
reaction
system.
mechanistic
study
suggested
that
key
pathway
might
involve
oxidative
addition/reduction
elimination,
whereas
aryl
‐C−H
was
mediated
σ
‐activation.
Density
functional
theory
calculations
also
high
stereoselectivity
due
to
steric
hindrance.
