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.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(22), P. 4610 - 4615
Published: May 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
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(16), P. 11783 - 11788
Published: July 26, 2024
The
construction
of
biologically
interesting
N-heterocycles
under
metal-free
conditions
is
a
constant
goal
in
industry
and
academia.
Herein,
we
have
developed
an
hexafluoroisopropanol
(HFIP)-mediated
intramolecular
cyclization
allenamides,
providing
tetrahydro-β-carboline
derivatives
embedded
with
C1-vinyl
functionality.
protocol
provided
atom-efficiently
room
temperature
broad
substrate
scope
good
to
excellent
yields.
potential
impact
the
further
highlighted
by
synthesizing
important
molecules
diversified
scaffolds
via
postsynthetic
modifications.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(30), P. 5557 - 5561
Published: July 22, 2022
An
efficient
method
for
the
synthesis
of
β,β-di(hetero)aryl-α,α-difluorinated
ketones
using
readily
available
organophosphonium
salts
and
difluoroenol
silyl
ethers
has
been
developed.
This
mild
reaction
features
a
good
functional
group
tolerance,
scaled-up
synthesis,
synthetic
simplicity.
By
taking
advantage
DMSO
as
less-toxic
promoter
solvent
difluoroalkylation
C–P
bond
functionalization,
use
transition-metal
catalysts
sensitive
additives
could
be
avoided.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(13), P. 2488 - 2493
Published: March 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.
A
facile
one-pot
synthesis
of
oxygen-
and
nitrogen-containing
benzoheterocycles
has
been
achieved
through
[4
+
1]
annulation
para
-quinone
methides,
followed
by
an
oxidation/elimination
sequence.
Chinese Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
42(11), P. 3562 - 3562
Published: Jan. 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.
Chemistry - A European Journal,
Journal Year:
2022,
Volume and Issue:
29(17)
Published: Dec. 28, 2022
The
solvent
effects
in
Friedel-Crafts
cycloalkylation
of
epoxides
and
Cope
rearrangement
aldimines
were
investigated
by
using
ab
initio
molecular
dynamics
simulations.
Explicit
treatments
applied
for
both
reactants
solvents.
reaction
mechanisms
elucidated
via
free
energy
calculations
based
on
metadynamics
results
reveal
that
reactions
proceed
a
concerted
fashion.
Key
solvent-substrate
interactions
are
identified
from
the
structures
transition
states
with
explicit
molecules.
remarkable
promotion
effect
hexafluoroisopropanol
is
ascribed
to
synergistic
H-bonding
networks
C-H/π
substrates.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(17), P. 4569 - 4574
Published: Jan. 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.
