Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(6)
Опубликована: Апрель 26, 2023
Abstract
A
NaH‐promoted
domino
reaction
between
azadiene
bearing
an
indene
moiety
with
Nazarov
reagent
was
developed.
variety
of
spiro[4.5]decane
derivatives
were
obtained
via
[4+2]
cycloaddition
good
yields
and
high
diastereoselectivity.
The
strategy
benefited
from
mild
conditions
very
broad
substrate
scope.
Furthermore,
a
gram‐scale
experiment
transformation
the
product
carried
out.
Lastly,
density
functional
theory
(DFT)
calculations
have
been
performed
to
verify
proposed
mechanism
analyze
observed
Chemical Reviews,
Год журнала:
2022,
Номер
122(24), С. 17479 - 17646
Опубликована: Окт. 14, 2022
Alkenes
and
their
derivatives
are
featured
widely
in
a
variety
of
natural
products,
pharmaceuticals,
advanced
materials.
Significant
efforts
have
been
made
toward
the
development
new
practical
methods
to
access
this
important
class
compounds
by
selectively
activating
alkenyl
C(sp2)–H
bonds
recent
years.
In
comprehensive
review,
we
describe
state-of-the-art
strategies
for
direct
functionalization
sp2
C–H
C–F
until
June
2022.
Moreover,
metal-free,
photoredox,
electrochemical
also
covered.
For
clarity,
review
has
divided
into
two
parts;
first
part
focuses
on
currently
available
using
different
alkene
as
starting
materials,
second
describes
bond
easily
accessible
gem-difluoroalkenes
material.
This
includes
scope,
limitations,
mechanistic
studies,
stereoselective
control
(using
directing
groups
well
metal-migration
strategies),
applications
complex
molecule
synthesis
where
appropriate.
Overall,
aims
document
considerable
advancements,
current
status,
emerging
work
critically
summarizing
contributions
researchers
working
fascinating
area
is
expected
stimulate
novel,
innovative,
broadly
applicable
functionalizations
coming
Organic Letters,
Год журнала:
2023,
Номер
25(26), С. 4908 - 4912
Опубликована: Июнь 23, 2023
A
decarboxylative/dehydrofluorinative
formal
[3
+
2]
cycloaddition
aromatization
of
isoquinolinium
N-ylides
with
difluoroenoxysilanes
has
been
developed.
This
methodology
provides
a
facile
and
straightforward
synthetic
pathway
to
afford
highly
functionalized
fluorinated
pyrrolo[2,1-a]isoquinolines
in
good
excellent
yields
under
mild
conditions.
Moreover,
gram-scale
derivatization
experiments
for
the
late-stage
functionalization
drug
molecules
have
also
demonstrated.
Ring-fluorinated
azaheterocycles
have
wide
applications
in
agrochemicals,
pharmaceuticals,
and
synthesis,
which
prompt
continuous
endeavors
to
expand
such
heterocyclic
families.
However,
monofluorinated
triazaheterocycles
hardly
been
explored.
This
work
reported
a
novel
modular
synthesis
of
1,2,4-triazoles
1,3,5-triazines,
utilizes
N-CF3
imidoyl
chlorides
as
unique
polyfluoro
synthons
their
defluorinative
annulations
with
hydrazines/imidazines.
Further
modifications
these
fluorinated
heterocycles
highlight
the
potential
method
for
accessing
functional
molecules.
Organic Letters,
Год журнала:
2024,
Номер
26(7), С. 1447 - 1451
Опубликована: Фев. 14, 2024
Difluoroenoxysilane,
a
commonly
used
difluoroallylating
reagent,
has
attracted
considerable
attention
in
recent
years.
However,
its
application
the
annulation
reaction
for
construction
of
fluorinated
heterocyclic
compounds
remains
relatively
limited.
Presented
here
is
Brønsted
acid-catalyzed
efficient
formal
[4
+
2]
difluoroenoxysilanes
with
α-cyano
chalcones.
The
developed
protocol
demonstrates
tolerance
to
various
substituents
under
mild
conditions,
providing
reliable
approach
construct
gem-difluoro-3,4-dihydro-2H-pyrans
good
excellent
yields
high
diastereoselectivities.
Organic Letters,
Год журнала:
2024,
Номер
26(22), С. 4610 - 4615
Опубликована: Май 23, 2024
An
oxa-6π-electrocyclization
of
difluoroenoxysilanes
with
diaryl
2-indolylmethanols
has
been
developed.
In
addition,
a
rarely
reported
C3-nucleophilic
[3+2]
cycloaddition
dialkyl
disclosed.
This
divergent
approach
affording
readily
available
as
three-atom
and
C2
synthons
provides
rapid
access
to
fluoro
2
Organic Letters,
Год журнала:
2022,
Номер
24(13), С. 2488 - 2493
Опубликована: Март 28, 2022
A
new
efficient
formal
[2
+
3]
cyclization
of
p-hydroxybenzyl
alcohols
with
difluoroenoxysilanes
has
been
established.
This
convenient
one-pot
sequential
procedure
enables
the
divergent
construction
highly
functionalized
gem-difluorinated
oxa-spirocyclohexadienones
under
mild
conditions.
As
opposed
to
common
C1
synthons
in
previous
studies,
acted
as
3-atom
(CCO)
for
first
time
here.
The
AcOH
and
H2O
generated
reaction
are
critical
reactions
proceed
smoothly.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(17), С. 4569 - 4574
Опубликована: Янв. 1, 2022
A
visible
light
promoted
direct
benzylic
C–H
difluoroalkylation
with
difluoroenoxysilanes
catalyzed
by
Na
2
-eosin
Y
via
a
HAT-ORPC
pathway
has
been
developed,
providing
an
efficient
and
atom-economic
method
for
production
of
α-benzyl-α,α-difluoroketones.
Chinese Journal of Organic Chemistry,
Год журнала:
2022,
Номер
42(11), С. 3562 - 3562
Опубликована: Янв. 1, 2022
Organofluorine
compounds
have
been
widely
applied
in
various
fields
ranging
from
drug
discovery,
clinical
medicines,
agrochemistry,
and
materials
science
to
organic
synthesis,
due
their
special
chemical
physical
properties
when
compared
with
nonfluorinated
analogs.In
the
past
decades,
significant
progress
has
made
development
of
selective
fluorination
fluoroalkylation
for
synthesis
structurally
diverse
fluorine-containing
molecules.Among
them,
α-fluoroalkylated
carbonyl
group
represents
an
important
class
scaffold
components
biologically
active
druglike
compounds.In
this
context,
based
on
use
difluorinated
silyl
enol
ether
(DFSEE)
as
a
unique
fluoroaklylating
reagent,
variety
methods
incorporation
gem-difluoroalkylated
moiety
achieved,
including
aldol,
Mannich,
arylation,
allylation,
protonation,
halogenation,
conjugate
addition,
olefination
reactions.On
other
hand,
DFSEEs
could
also
merge
new
types
reactions
such
radical-type
difluoroalkylation
cascade
reaction
by
virtue
incredible
reactive
flexibility.In
O-site
addition
was
reported,
enabling
construction
versatile
gem-difluoroalkenes.Given
importance
organofluorine
synthetic
potential
these
avenues,
herein,
we
highlight
recent
advances
functionalization
gem-difluorinated
ethers,
which
serve
key
building
blocks
compounds.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(9), С. 1413 - 1418
Опубликована: Апрель 12, 2023
Abstract
Hexafluoroisopropanol
(HFIP)
has
been
extensively
applied
in
organic
synthesis
as
a
versatile
reaction
media.
However,
the
application
of
HFIP
an
catalyst
rarely
studied.
Presented
here,
is
example
HFIP‐catalyzed
Mannich‐type
between
quinoxalin‐2(1
H
)‐ones
and
difluoroenoxysilanes.
The
developed
protocol
tolerates
various
substituents
under
mild
conditions,
providing
divergent
approach
to
construction
difluoro‐substituted
3,4‐dihydroquinoxalin‐2(1
monofluoroquinoxalin‐2(1
51–92%
yields.
magnified
image
