Molecules,
Journal Year:
2023,
Volume and Issue:
28(14), P. 5529 - 5529
Published: July 20, 2023
An
unprecedented
N-alkylation
of
3-nitroindoles
with
para-quinone
methides
was
developed
for
the
first
time.
Using
potassium
carbonate
as
base,
a
wide
range
structurally
diverse
N-diarylmethylindole
derivatives
were
obtained
moderated
to
good
yields
via
protection
group
migration/aza-1,6-Michael
addition
sequences.
The
reaction
process
also
demonstrated
by
control
experiments.
Different
from
previous
advances
where
3-nitrodoles
served
electrophiles
trapping
various
nucleophiles,
herein
is
featured
that
defined
latent
N-centered
nucleophiles
react
ortho-hydrophenyl
p-QMs
construction
N-diarylmethylindoles.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(7), P. 4790 - 4798
Published: March 29, 2023
A
hexafluoroisopropanol
(HFIP)-promoted
hydroxydifluoromethylation
of
aniline,
indole,
and
pyrrole
derivatives
with
difluoroacetaldehyde
ethyl
hemiacetal
has
been
developed.
This
protocol
provides
a
facile
straightforward
approach
to
access
diverse
difluoromethylated
carbinols
in
good
excellent
yields
under
mild
conditions.
Furthermore,
gram-scale
synthetic
derivatization
experiments
have
also
demonstrated.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(3), P. 751 - 756
Published: Jan. 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.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(26), P. 4908 - 4912
Published: June 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.
Synthesis,
Journal Year:
2024,
Volume and Issue:
56(11), P. 1756 - 1764
Published: Jan. 25, 2024
Abstract
A
facile
and
efficient
method
for
the
synthesis
of
trifluoromethylated
carbinols
has
been
developed
from
imidazo[1,2-a]pyridines
trifluoroacetaldehyde.
The
direct
C(sp2)–H
hydroxytrifluoromethylation
is
successfully
implemented
at
room
temperature
using
HFIP
as
solvent
through
dehydrative
cross-coupling
process,
which
displays
a
broad
substrate
scope
functional
group
tolerance.
Furthermore,
gram-scale
synthetic
transformation
experiments
have
also
demonstrated,
indicate
its
potential
applicable
values
in
organic
synthesis.
This
green
protocol
features
operational
simplicity,
atom
economy,
mild
reaction
conditions
(e.g.,
temperature,
transition-metal-
oxidant-free,
without
inert
gas
protection),
wide
scope,
excellent
practicality.
Chemical Communications,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
A
cascade
of
two
C–C
bond
forming
reactions
promoted
alone
by
HFIP
is
described
delivering
tetrahydro-β-carboline
derivatives
embedded
with
an
allylic
amine
functionality.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(10), P. 7347 - 7351
Published: Jan. 2, 2024
Incorporating
fluorinated
moieties
into
organic
molecules
is
an
attractive
strategy
to
enhance
drug-like
properties.
Herein,
we
have
developed
a
simple
and
self-promoted
protocol
for
hexafluoroisopropoxylation
trifluoroethoxylation
of
allenamides
with
alcohols
such
as
HFIP
TFE.
The
reaction
provided
the
fluoroalkoxylated
products
in
regio-
stereoselective
manner
good
moderate
yields
under
mild
conditions.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 27, 2025
Herein,
we
present
an
acid-
and
base-mediated
approach
for
ring
opening
of
donor-acceptor
cyclopropanes
(DACs)
followed
by
(3+2)
annulation,
yielding
biologically
relevant
gem-difluorinated
cyclopentenes
via
α,α-difluoroketone
scaffolds.
Fluorinated
rings
are
essential
building
blocks
in
drug
discovery
materials
research.
This
methodology
has
a
broad
substrate
scope,
is
scalable,
provides
practical
synthetic
route
to
obtain
value-added
fluorinated
compounds.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(21), P. 14753 - 14762
Published: Oct. 18, 2022
The
synthesis
of
N-heterocycles
composes
a
significant
part
synthetic
chemistry.
In
this
report,
Cu(II)-catalyzed
green
and
efficient
pyrrolo[1,2-a]quinoxaline,
quinazolin-4-one,
benzo[4,5]imidazoquinazoline
derivatives
was
developed,
employing
N,N-dimethylethanolamine
(DMEA)
as
C1
synthon.
Green
oxidant
O2
is
critical
in
these
transformations,
facilitating
the
formation
key
intermediate─a
reactive
iminium
ion.
method
conducted
under
mild
conditions
compatible
with
diversity
functional
groups,
providing
an
appealing
alternative
to
previously
developed
protocols.
