Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(8), С. 2170 - 2176
Опубликована: Фев. 25, 2021
Abstract
Herein,
we
report
a
Palladium(0)‐catalyzed
C4
site‐selective
C−H
difluoroalkylation
of
isoquinolin‐1(
2H
)‐ones
through
radical
pathway.
The
present
reaction
enables
the
preparation
2,2‐difluoro‐2‐(1‐oxo‐1,2‐dihydroisoquinolin‐4‐yl)acetates/acetamides
direct
cross‐coupling
readily
available
with
2‐bromo‐2,2‐difluoroacetates
or
2‐bromo‐2,2‐difluoroacetamides.
Therefore,
this
method
provides
an
efficient
and
convenient
approach
to
install
difluoroacetate
difluoroacetamide
moiety
into
bioactive
molecules.
Bioassay
results
showed
that
introduction
these
difluorinated
groups
at
position
was
beneficial
improve
their
antiviral
activity
compound
5
ab
found
exhibit
similar
commercial
Ningnanmycin.
magnified
image
ACS Catalysis,
Год журнала:
2021,
Номер
11(9), С. 4929 - 4935
Опубликована: Апрель 8, 2021
Control
of
regioselectivity
that
defies
the
intrinsic
reactivity
arene
C–H
bonds
remains
a
formidable
challenge.
In
this
work,
dimeric
Rh(II)
complexes
have
been
applied
as
an
efficient
catalyst
for
regioselective
coupling
NH
indoles
with
diazo
compounds.
Two-substituted
mostly
reacted
C(6)
selectivity.
Mechanistic
studies
revealed
results
from
hydrogen-bonding
directing
effect,
and
C–C
bond
formation
proceeds
via
Friedel–Crafts-type
attack
indole
toward
carbene
species.
contrast,
reaction
4-methoxyindoles
occurred
exclusively
complementary
C(7)
Advanced Functional Materials,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 23, 2025
Abstract
Rice,
a
major
global
food
crop,
faces
considerable
challenges
from
herbicide
damage,
particularly
pre‐emergent
herbicides
like
Pretilachlor
(Pre).
Herbicide‐resistant
rice
varieties
and
efficient,
environmentally
friendly
safeners
for
Pre
are
still
lacking.
Substituted
salicylic
acid
show
the
potential
to
relieve
damage
but
limited
by
poor
solubility
penetration.
This
study
explores
novel
substituted
derivative
salt,
matrine
(MT)‐3‐nitrosalicylic
(3‐NO
2
SA)
salt
(MNS),
as
safener
Pre.
MNS,
with
enhanced
solubility,
demonstrated
better
penetration
in
cells
than
fenclorin
(Fen),
only
commercial
Pre,
which
is
less
effective
poses
environmental
risks.
MNS
activates
glutathione
metabolism
detoxification
pathway
more
effectively
Fen,
leading
superior
safening
effect.
To
further
enhance
plant
uptake,
loaded
into
supramolecular
nanocarrier,
beta‐hydroxycyclodextrin
(HBPCD),
fabricate
nanoformulation
(MNS@HBPCD).
In
field
trials,
MNS@HBPCD
outperformed
improving
26%
seedlings
number,
15%
shoot
height,
9%
root
length,
27%
fresh
weight,
14%
yield,
while
maintaining
Pre's
herbicidal
efficacy.
Toxicity
tests
indicated
that
it
significantly
toxic
zebrafish
embryos,
HepG2
cells,
HaCaT
Fen.
Thus,
shows
promise
an
crop
protection
material
mitigates
damage.
Chemical Science,
Год журнала:
2021,
Номер
12(11), С. 4126 - 4131
Опубликована: Янв. 1, 2021
Direct
para-selective
C-H
functionalization
of
arenes
remains
a
daunting
challenge
and
is
still
significantly
restricted
to
few
scaffolds.
Herein,
we
report
an
unprecedented
pyridine-based
para-directing
template
(DT)
assisted,
Pd-catalyzed
para-C-H
alkenylation
three
classes
arenes,
i.e.
phenylpropanoic
acids,
2-phenyl
benzoic
acids
benzyl
alcohols,
with
series
alkenes
including
perfluoroalkenes.
Notably,
the
para-DT
could
be
easily
synthesized
readily
recycled
under
mild
conditions.
These
results
may
find
application
in
rapid
construction
para-substituted
stimulate
exploration
novel
methods
for
arenes.
Angewandte Chemie International Edition,
Год журнала:
2021,
Номер
60(35), С. 19030 - 19034
Опубликована: Июнь 23, 2021
Abstract
The
direct
incorporation
of
a
trifluoromethyl
group
on
an
aromatic
ring
using
radical
pathway
has
been
extensively
investigated.
However,
the
highly
para
‐selective
C−H
trifluoromethylation
class
arenes
not
achieved.
In
this
study,
we
report
light‐promoted
4,5‐dichlorofluorescein
(DCFS)‐enabled
arylcarbamates
Langlois
reagent.
preliminary
mechanistic
study
revealed
that
activated
organic
photocatalyst
coordinated
with
arylcarbamate
led
to
trifluoromethylation.
Ten‐gram
scale
reaction
performs
well
highlighting
synthetic
importance
new
protocol.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(5), С. 3546 - 3554
Опубликована: Фев. 16, 2022
Visible-light-induced,
iridium
catalyzed,
para-selective
C-H
difluoroalkylation
of
aniline
derivatives
under
mild
reaction
conditions
is
reported.
Various
substrates
and
bioactive
compounds,
such
as
precursors
vorinostat
chlorpropham,
were
all
well
tolerated.
This
protocol
features
a
wide
substrate
scope,
high
regioselectivity,
low
catalyst
usage,
operational
simplicity.
Organic Letters,
Год журнала:
2022,
Номер
24(10), С. 2002 - 2007
Опубликована: Март 8, 2022
An
iridium-catalyzed,
reductive
alkylation
of
abundant
tertiary
lactams
and
amides
using
1–2
mol
%
Vaska's
complex
(IrCl(CO)(PPh3)2),
tetramethyldisiloxane
(TMDS),
difluoro-Reformatsky
reagents
(BrZnCF2R)
for
the
general
synthesis
medicinally
relevant
α-difluoroalkylated
amines
is
described.
A
broad
scope
(46
examples),
including
N-aryl-
N-heteroaryl-substituted
lactams,
demonstrated
an
excellent
functional
group
tolerance.
Furthermore,
late-stage
drug
functionalizations,
a
gram-scale
synthesis,
common
downstream
transformations
proved
potential
synthetic
relevance
this
new
methodology.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(17), С. 12585 - 12596
Опубликована: Авг. 16, 2023
The
development
of
sustainable
and
mild
protocols
for
the
fluoroalkylation
organic
backbones
is
current
interest
in
chemical
synthesis.
Herein,
we
present
operationally
simple
practical
transition-metal-free
methods
preparation
difluoroalkyl
anilines.
First,
a
visible-light
organophotocatalytic
system
working
via
oxidative
quenching
described,
providing
access
to
wide
range
anilines
under
conditions.
In
addition,
formation
an
unprecedented
electron
donor-acceptor
(EDA)
complex
between
ethyl
difluoroiodoacetate
reported
exploited
as
alternative,
efficient,
straightforward
strategy
prepare
derivatives.
