ACS Catalysis,
Год журнала:
2024,
Номер
15(2), С. 759 - 767
Опубликована: Дек. 25, 2024
A
synthetic
strategy
for
the
catalytic
cycloaddition
of
α-trifluoromethyl-α-diazoketones
with
nitriles
has
been
achieved
based
on
cobalt(II)
metalloradical
catalysis.
The
easily
accessible
starting
materials,
cost-effective
catalyst,
and
experimental
simplicity
rendered
this
protocol
a
robust
practical
approach
to
construct
diverse
functionalized
4-CF3-substituted
oxazoles
high
efficiency.
wide
substrate
scope
both
α-trifluoromethylated
diazoketones
is
amenable
system.
level
functional
group
tolerance
provides
several
opportunities
precise
late-stage
modifications
bioactive
drug-like
molecules.
Mechanistic
experiments
spectroscopic
investigations
confirm
radical
nature
reaction
reveal
involvement
monocarbene
biscarbene
intermediates
during
process.
Organic Letters,
Год журнала:
2023,
Номер
25(32), С. 6001 - 6005
Опубликована: Авг. 7, 2023
An
electrochemical
facilitated
three-component
trifluoromethylation/spirocyclization
reaction
of
N-(arylsulfonyl)acrylamides,
CF3SO2Na,
and
H2O
has
been
developed.
Without
the
requirement
chemical
oxidants,
a
number
unexplored
trifluoromethylated
4-azaspiro[4.5]decanes
were
obtained
in
satisfactory
yields
under
mild
conditions.
This
work
provides
new
synthetic
strategy
for
fluorine-containing
spirocyclic
compounds
shows
perspective
reactivity
study
N-(arylsulfonyl)acrylamides.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 20, 2025
In
this
paper,
the
application
of
α-methyl
secondary
enaminones
in
synthesis
tetrahydrofuropyridines
is
described.
The
key
step
methodology
situ
generation
1-azadiene
from
oxidation
enaminone,
followed
by
a
subsequent
inverse-electron-demand
hetero-Diels–Alder
reaction
proceeded
to
give
desired
product.
Mechanistic
studies
and
density
functional
theory
(DFT)
calculations
revealed
detailed
pathway.
Gram-scale
preparation
experiments
further
transformation
product
demonstrate
potential
applicability
method.
addition,
amide
derivatives
could
be
obtained
employing
β-methyl
as
substrates
under
similar
oxidative
conditions.
present
work
opens
new
window
rarely
reported
enaminones.
Enones
with
β-electron-donating
groups
can
exist
in
their
zwitterionic
resonance
forms,
which
favor
nucleophilic
attack
to
phosphenes
generated
from
phosphoryl
(aryl)diazomethanes
under
blue
light
irradiation
yield
intermediates.
The
intermediates
cyclize
afford
highly
stereoselective
trans-3,4-dihydro-1,2-oxaphosphinine
2-oxides
good
excellent
yields.
In
the
cyclic
transition
state
of
final
cyclization,
stereoelectronic
effect
and
Coulomb
force
control
high
stereoselectivity.
electron-donating
enones
play
double
roles
both
cyclization.
reaction
features
readily
available
starting
materials,
atom-economy,
no
catalyst,
a
fast
rate,
broad
functional
group-tolerance
substrate
scope,
yields
stereoselectivity,
mild
conditions.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(19), С. 4139 - 4144
Опубликована: Июль 2, 2024
Abstract
A
copper‐catalyzed
annulation
of
enaminones
with
maleimides
was
developed
to
synthesize
various
pyrrolo[3,4‐e]isoindoles.
In
this
strategy,
2‐aminopyridine
served
as
a
traceless
directing
group,
and
target
products
were
obtained
in
54–72%
yields.
Moreover,
plausible
mechanism
for
reaction
proposed
based
on
several
control
experiments,
deuterium
exchange
previous
reports.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
β-Enaminone
transformation
strategies
are
widely
employed
in
the
synthesis
of
numerous
biologically
active
drugs
and
natural
products,
highlighting
their
significance
medicinal
chemistry.
Authorea (Authorea),
Год журнала:
2024,
Номер
unknown
Опубликована: Июнь 8, 2024
An
efficient
copper-catalyzed
annulation
of
enaminones
with
maleimides
has
been
developed.
This
reaction
provides
a
practical
approach
towards
the
synthesis
various
pyrrolo[3,4-e]isoindoles
in
moderate
to
good
yields.
Notable
features
method
include
use
2-aminopyridine
group
as
traceless
directing
group,
wide
scope
substrates
functional
compatibility
and
applicability
gram
scale.
Abstract
We
herein
developed
a
base-promoted
cyclization
reaction
between
N-acyl
benzotriazoles
and
p-toluenesulfonylmethyl
isocyanide
(TosMIC)
to
afford
4,5-disubstituted
oxazoles.
In
the
presence
of
3
equiv
K3PO4,
two
readily
available
starting
materials
reacted
in
N,N-dimethylformamide
at
80
°C
give
28
examples
4-tosyl-5-aryl,
-alkyl,
or
-alkenyl-substituted
oxazoles
moderate
high
yields.
RSC Advances,
Год журнала:
2024,
Номер
14(38), С. 28210 - 28214
Опубликована: Янв. 1, 2024
A
strategy
for
C–O
bond
cleavage
of
ester
the
synthesis
substituted
oxazoles
was
developed.
The
proceeded
smoothly
under
metal-free
conditions,
combining
cleavage,
C–N
and
formation
in
one
pot.
