ACS Catalysis,
Год журнала:
2023,
Номер
13(19), С. 12755 - 12765
Опубликована: Сен. 15, 2023
Typically,
trimethylsilyl
isothiocyanate
(TMSNCS)
is
used
as
a
nucleophilic
thiocyanate
building
block
(−S–C≡N)
that
reacts
with
various
electrophiles.
However,
it
has
been
less
explored
source
of
isothiocyanates
(−N═C═S),
which
can
usually
be
converted
by
thermal
isomerization
allyl
or
propargyl
thiocyanates.
Achieving
method
precise
site
control
even
more
challenging.
Here,
we
demonstrate
an
approach
uses
metal
catalysts
to
switchable
sites
and
provide
strategy
construct
CF3-containing
thiazoles
allenes
via
the
multicomponent
reaction
1,3-enynes,
TMSNCS,
electrophilic
trifluoromethyl
reagent.
In
presence
inexpensive
Fe(III)
Cu(II)
catalysts,
current
practical
convenient,
compatible
substrates
bearing
sensitive
functional
groups
readily
transferred
complex
scaffolds.
The
biological
evaluation
showed
two
developed
exhibited
dramatic
inhibitory
activities
for
three
human
cancer
cell
lines
beyond
those
5-fluorouracil.
Both
compounds
increased
level
reactive
oxygen
species
in
MCF-7
cells,
believed
early
step
tumor
apoptosis.
Chemical Reviews,
Год журнала:
2021,
Номер
122(2), С. 2487 - 2649
Опубликована: Ноя. 9, 2021
Redox
processes
are
at
the
heart
of
synthetic
methods
that
rely
on
either
electrochemistry
or
photoredox
catalysis,
but
how
do
and
catalysis
compare?
Both
approaches
provide
access
to
high
energy
intermediates
(e.g.,
radicals)
enable
bond
formations
not
constrained
by
rules
ionic
2
electron
(e)
mechanisms.
Instead,
they
1e
mechanisms
capable
bypassing
electronic
steric
limitations
protecting
group
requirements,
thus
enabling
chemists
disconnect
molecules
in
new
different
ways.
However,
while
providing
similar
intermediates,
differ
several
physical
chemistry
principles.
Understanding
those
differences
can
be
key
designing
transformations
forging
disconnections.
This
review
aims
highlight
these
similarities
between
comparing
their
underlying
principles
describing
impact
electrochemical
photochemical
methods.
Chinese Journal of Chemistry,
Год журнала:
2022,
Номер
40(21), С. 2582 - 2594
Опубликована: Июль 18, 2022
Comprehensive
Summary
Trifluoromethyl
group
is
one
of
the
most
frequently
available
and
promising
functional
groups
in
pharmaceutical,
agrochemical
as
well
material
molecules.
Developing
synthetic
methods
for
synthesis
trifluoromethyl
functionalized
compounds
by
trifluoromethylation
reactions
occupies
significant
position
modern
organic
chemistry.
On
other
hand,
a
typical
tool
sustainable
synthesis,
transition
metal‐free
possesses
unique
advantages
atom
economy,
easy
product
purification
excellent
eco‐tolerance.
Consequently,
constitute
important
approaches
accessing
trifluoromethylated
Herein,
advances
C—H
are
reviewed
first
time.
According
to
updated
state‐of‐art,
both
catalytic
conventional
heating
chemistry
more
photocatalysis
included,
covering
C(sp
3
)–H
bond,
aromatic
2
bond
non‐aromatic
different
substrates
over
last
five
years
(2017—2021).
Russian Chemical Reviews,
Год журнала:
2023,
Номер
92(12), С. RCR5104 - RCR5104
Опубликована: Дек. 1, 2023
After
the
appearance
of
green
chemistry
concept,
which
was
introduced
in
vocabulary
early
1990s,
its
main
statements
have
been
continuously
developed
and
modified.
Currently,
there
are
10–12
cornerstones
that
should
form
basis
for
an
ideal
chemical
process.
This
review
analyzes
accumulated
experience
achievements
towards
design
products
processes
reduce
or
eliminate
use
generation
hazardous
substances.
The
presents
views
leading
Russian
scientists
specializing
various
fields
this
subject,
including
homogeneous
heterogeneous
catalysis,
fine
basic
organic
synthesis,
electrochemistry,
polymer
chemistry,
based
on
bio-renewable
feedstocks
energetic
compounds
materials.
A
new
approach
to
quantitative
evaluation
environmental
friendliness
by
authors
is
described.
<br>
bibliography
includes
1761.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(28), С. 19286 - 19294
Опубликована: Июль 3, 2024
As
one
of
the
most
powerful
trifluoromethylation
reagents,
(trifluoromethyl)trimethylsilane
(TMSCF3)
has
been
widely
used
for
synthesis
fluorine-containing
molecules.
However,
to
best
our
knowledge,
simultaneous
incorporation
both
TMS-
and
CF3-
groups
this
reagent
onto
same
carbon
products
not
realized.
Herein,
we
report
an
unprecedented
SmI2/Sm
promoted
deoxygenative
difunctionalization
amides
with
TMSCF3,
in
which
silyl
trifluoromethyl
are
incorporated
into
final
product,
yielding
α-silyl-α-trifluoromethyl
amines
high
efficiency.
Notably,
group
could
be
further
transformed
other
functional
groups,
providing
a
new
method
α-quaternary
α-CF3-amines.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(15), С. 1691 - 1698
Опубликована: Март 19, 2024
Comprehensive
Summary
A
novel
electrochemical
multicomponent
cascade
reaction
of
indole‐tethered
alkenes
with
CF
3
SO
2
Na
and
n
‐Bu
4
NI
has
been
developed,
which
enables
the
rapid
assembly
spiropyrrolidinyl‐oxindoles
in
good
yields.
The
experimental
results
DFT
calculations
suggest
that
this
proceeds
through
oxidation
Na,
radical
coupling
alkene,
spirocyclization,
sulfinate,
iodide
substitution,
water
coupling.
This
strategy
features
mild
conditions,
easy‐to‐handle
reactants,
chemical
finding
not
only
enriches
research
contents
but
also
provides
a
green
for
construction
compared
existing
methodologies.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(15), С. 1679 - 1685
Опубликована: Март 15, 2024
Comprehensive
Summary
A
novel
and
eco‐friendly
electrochemical
activation
of
trifluoromethyl
thianthrenium
triflate
(TT–CF
3
+
OTf
−
)
for
trifluoromethylation
imidazole‐fused
heteroaromatic
compounds
was
established.
This
method
involves
the
direct
electrolysis
TT–CF
without
requirement
external
oxidants
or
catalysts,
aligning
with
principles
green
chemistry.
wide
range
including
imidazo[1,2‐
a
]pyridines
benzo[
d
]imidazo[2,1‐
b
]thiazoles
have
been
successfully
trifluoromethylated
using
this
technique,
exhibiting
excellent
compatibility
various
functional
groups
broad
substrate
scope.
Moreover,
method's
applicability
one‐pot
sequential
reactions
enables
reduction
waste
resource
consumption
by
eliminating
need
intermediate
purification
steps.
Chemical Science,
Год журнала:
2021,
Номер
12(36), С. 12036 - 12045
Опубликована: Янв. 1, 2021
DNA-encoded
library
(DEL)
technology
facilitates
the
rapid
identification
of
therapeutic
candidates
in
pharmaceutical
settings.
Herein,
development
photoredox-mediated
hydrocarbofunctionalization
protocols
olefins
is
described.
