Organic Letters,
Год журнала:
2023,
Номер
25(38), С. 7057 - 7061
Опубликована: Сен. 13, 2023
A
TFA-catalyzed
dehydrofluorinative
cyclization
of
2,2-difluoro-3-hydroxy-1,4-diketones
has
been
developed
in
the
presence
amines
under
mild
conditions
which
difluorinated
substrates
are
readily
prepared
according
to
our
reported
literature.
This
protocol
provides
a
rapid
construction
fluoro
3(2H)-furanones
good
excellent
yields
with
functional
group
tolerance.
Easy
scale-up
synthesis
also
shows
practical
advantage.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8420 - 8434
Опубликована: Июнь 5, 2024
An
elegant
and
highly
concise
strategy
for
the
construction
of
coumarin-functionalized
pyrrolo[2,1-a]isoquinolines
from
available
propargylamines
isoquinolinium
N-ylides
has
been
disclosed.
In
this
reaction,
acted
as
a
C2
synthon
to
form
coumarin
ring
well
1,3-dipole
construct
pyrrole
in
single
pot.
This
cascade
process
involves
1,4-conjugate
addition/lactonization/1,3-dipolar
cycloaddition
four
chemical
bonds
(one
C–O
bond
three
C–C
bonds)
two
new
heterocyclic
skeletons.
Additionally,
most
these
compounds
showed
good
fluorescence
properties
exhibited
high
molar
extinction
coefficient
large
Stokes
shifts.
Organic Letters,
Год журнала:
2024,
Номер
26(3), С. 751 - 756
Опубликована: Янв. 12, 2024
A
highly
diastereoselective
[3
+
2]
cycloaddition
of
aziridines
with
difluorinated
silyl
enol
ethers
has
been
developed.
This
approach
provides
a
facile
methodology
for
functionalized
gem-difluorinated
pyrrolidines
in
good
to
excellent
yields
functional
group
tolerance.
one-pot,
two-step
synthesis
structurally
interesting
fluorinated
pyrroles
also
developed
through
cycloaddition/aromatization/desulfonation
sequence.
Moreover,
readily
available
substrates,
mild
reaction
conditions,
and
easy
scale-up
show
practical
advantages.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(5), С. 2847 - 2857
Опубликована: Фев. 16, 2024
In
recent
years,
the
application
of
fluorinated
alcohols
as
solvents,
cosolvents,
or
additives
has
become
important
in
modern
organic
synthesis.
However,
their
potential
efficient
catalysts
synthesis
not
been
well-explored.
this
article,
we
report
on
development
a
one-pot
sequential
cascade
reaction
p-quinone
methides
with
difluoroenoxysilanes
using
hexafluoroisopropanol
catalyst.
This
allows
for
preparation
multisubstituted
oxa-spiro[4,5]cyclohexadienones.
By
50
mol
%
1,1,1,3,3,3-Hexafluoroisopropanol
(HFIP),
proceeds
smoothly
to
yield
1,6-conjugated
products,
which
are
then
subjected
oxidative
dearomatization/hemiacetalization
PhI(OAc)2.
The
overall
process
affords
moderate
high
yields
and
excellent
diastereoselectivities.
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.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 19, 2025
A
straightforward
and
efficient
strategy
for
the
synthesis
of
fully
functionalized
indolizines
has
been
developed
through
a
transition
metal-
oxidant-free
[3
+
2]
cycloaddition
reaction
zwitterionic
ketenimines
pyridinium
salts.
This
versatile
method
proceeds
under
mild
conditions,
affording
in
moderate
to
good
yields.
approach
involves
an
intermolecular
cycloaddition,
followed
by
enamine/imine
tautomerization
aromatization.
Notably,
this
demonstrates
broad
functional
group
compatibility
allows
facile
scalability,
making
it
valuable
tool
indolizine-based
frameworks
organic
medicinal
chemistry.
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.
Chemical Communications,
Год журнала:
2023,
Номер
60(7), С. 831 - 834
Опубликована: Дек. 15, 2023
We
herein
report
regio-
and
enantioselective
arylation
of
β,γ-alkynyl-α-imino
esters
with
pyrroloisoquinolines.
Using
chiral
phosphoric
acid
catalysts,
a
wide
range
novel
axially
tetrasubstituted
α-amino
allenoates
were
accessed
in
good
yields
excellent
enantioselectivities.
Notably,
this
transformation
occurred
preferentially
at
the
sterically
more
hindered
C1-position
The
potential
scalability
late-stage
functionalization
demonstrated
utility
current
protocol.
