The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
85(23), С. 15667 - 15675
Опубликована: Ноя. 11, 2020
A
copper-catalyzed
bromodifluoroacetylative
cyclization
reaction
is
described.
The
treatment
of
bromodifluoroacete
derivatives
by
CuI
and
B2Pin2
enables
difluoroalkyl
radical
generation
triggers
the
addition/cyclization/bromination
sequences.
Bromodifluoroacetyl-derived
ester,
amide,
ketone
were
compatible
gave
various
vinyl
C-Br
bonds
containing
functionalized
heterocycles
in
good
yields.
Chemical Society Reviews,
Год журнала:
2020,
Номер
49(24), С. 9197 - 9219
Опубликована: Янв. 1, 2020
Halodifluoromethyl
and
trifluoromethyl-containing
compounds
can
act
various
rolesviaselective
cleavage
modes
to
access
more
valuable
fluorinated
or
nonfluorinated
molecules.
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
362(17), С. 3448 - 3484
Опубликована: Июнь 18, 2020
Abstract
It
is
well
known
that
heterocycles
are
among
the
most
significant
molecules
for
everyday
life,
ranging
from
natural
products
and
bioactive
substances
to
functional
materials.
This
review
will
focus
on
synthesis
of
by
reactions
involving
elemental
sulfur
published
2017
until
now.
magnified
image
Science China Chemistry,
Год журнала:
2021,
Номер
64(10), С. 1630 - 1659
Опубликована: Авг. 30, 2021
Abstract
The
unique
properties
of
fluorine-containing
organic
compounds
make
fluorine
substitution
attractive
for
the
development
pharmaceuticals
and
various
specialty
materials,
which
have
inspired
evolution
diverse
C-F
bond
activation
techniques.
Although
many
advances
been
made
in
functionalizations
activated
bonds
utilizing
transition
metal
complexes,
there
are
fewer
approaches
available
nonactivated
due
to
difficulty
oxidative
addition
metals
inert
bonds.
In
this
regard,
using
Lewis
acid
abstract
fluoride
light/radical
initiator
generate
radical
intermediate
emerged
as
powerful
tools
activating
those
Meanwhile,
these
transition-metal-free
processes
greener,
economical,
pharmaceutical
industry,
without
heavy
residues.
This
review
provides
an
overview
recent
activations
under
conditions.
key
mechanisms
involved
demonstrated
discussed
detail.
Finally,
a
brief
discussion
on
existing
limitations
field
our
perspective
presented.
Organic Letters,
Год журнала:
2023,
Номер
25(3), С. 512 - 516
Опубликована: Янв. 12, 2023
Switchable
multicomponent
reactions
have
been
attractive
tools
for
the
construction
of
compound
libraries
with
skeleton
diversity
and
complexity
by
slightly
changing
reaction
conditions.
Described
herein
is
a
regioselectivity-switchable
formal
[1
+
2
2]
cycloaddition
from
difluoroalkyl
compounds,
enaminones,
RNHNH2,
ultimately
using
1-methylindazol-3-amine
as
traceless
mediator
to
switch
inherent
regioselectivity
1,3,4-trisubstituted
pyrazole
formation
1,4,5-trisubstituted
pyrazoles.
Remarkable
features
this
work
include
mild
conditions,
simple
operation,
broad
scopes.
Journal of the American Chemical Society,
Год журнала:
2018,
Номер
140(29), С. 9061 - 9065
Опубликована: Июль 10, 2018
A
copper-catalyzed
system
has
been
introduced
for
the
enantioselective
defluoroalkylation
of
linear
1-(trifluoromethyl)alkenes
through
C-F
activation
to
synthesize
various
gem-difluoroalkenes
as
carbonyl
mimics.
For
first
time,
arylboronate-activated
alkyl
Grignard
reagents
were
uncovered
in
this
cross-coupling
reaction.
Mechanistic
studies
confirmed
that
tetraorganoborate
complexes
generated
situ
key
reactive
species
transformation.
ACS Central Science,
Год журнала:
2020,
Номер
6(10), С. 1819 - 1826
Опубликована: Авг. 31, 2020
Transition-metal-
or
oxidant-promoted
deconstructive
functionalizations
of
noncyclic
carbon–nitrogen
bonds
are
well
established,
usually
only
leaving
one
moiety
functionalized
toward
the
final
product.
In
contrast,
concomitant
C-
and
N-functionalizations
via
unstrained
C(sp3)–N
bond
under
metal-
oxidant-free
conditions
very
rare,
which
would
favorably
confer
versatility
product
diversity.
Disclosed
herein
is
first
difluorocarbene-induced
embodying
successive
cleavage
cyclic
amines
synchronous
functionalization
both
constituent
atoms
be
preserved
in
eventual
molecular
outputs
transition-metal-free
conditions.
Correspondent
access
to
deuterated
formamides
with
ample
isotopic
incorporation
was
demonstrated
by
a
switch
heavy
water
conceivably
useful
pharmaceutical
sciences.
The
current
strategy
remarkably
administers
convenient,
operationally
simple
novel
method
diversity
from
readily
available
starting
materials.
Therefore,
we
project
that
these
findings
broad
interest
research
endeavors
encompassing
fluorine
chemistry,
carbene
C–N
activation,
as
medicinal
chemistry.
Organic Letters,
Год журнала:
2020,
Номер
22(14), С. 5284 - 5288
Опубликована: Июнь 30, 2020
A
three-component
strategy
for
the
synthesis
of
thiazoles
and
isothiazoles
has
been
developed
by
employing
enaminoesters,
fluorodibromoiamides/ester,
sulfur.
The
were
formed
via
two
C–F
bond
cleavages
along
with
formation
new
C–S,
C–N,
N–S
bonds.
provides
high
selectivity
thiazoles/isothiazoles,
which
have
vital
applications
in
drug
discovery
development.
Organic Letters,
Год журнала:
2021,
Номер
23(21), С. 8343 - 8347
Опубликована: Окт. 12, 2021
Here
we
develop
a
novel
visible-light-driven
three-component
cyclization
by
trapping
an
1,3-vinylimine
ion
intermediate
for
the
direct
synthesis
of
pyrimido[1,2-b]indazole
derivatives
from
bromodifluoroacetic
acid
derivatives,
enaminones,
and
3-aminoindazoles
under
mild
conditions.
Notably,
robust
methodology
provides
valuable
opportunity
introduction
aliphatic
substituents
enables
good
compatibility
complex
bioactive
molecules.
Furthermore,
this
is
first
example
photoinduced
multicomponent
reaction
employing
as
C1-synthon.
