The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 6, 2025
A
water-controlled
geminal
phosphinoylation
of
enaminones
with
H-phosphine
oxides
has
been
established
through
AlCl3-mediated
C-N
bond
cleavage
in
this
work,
which
provides
a
novel
strategy
for
accessing
various
hydroxy
and
diphosphinoyl
products
3a
4a
high
yields.
The
transformation
features
excellent
functional
group
tolerance,
operational
simplicity,
atom
economy,
is
amenable
complex
molecule
skeletons.
Preliminary
mechanism
studies
suggest
the
conversion
from
to
involve
elimination
hydroxyl
group,
water
temperature
plays
critical
role
influencing
reaction
pathway
product
selectivity.
This
research
significant
value
functionalization
enaminones.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(15), С. 1727 - 1733
Опубликована: Март 26, 2024
Comprehensive
Summary
Chemodivergent
synthesis
of
benzofurans
and
2,3‐dihydrobenzofurans
has
been
realized.
Under
a
reaction
system
consisting
DBDMH
K
2
CO
3
as
promotors,
controlled
conditions
enabled
the
formation
two
sets
valuable
heterocycles
from
tandem
transformation
enaminones
salicylaldehydes.
The
key
to
success
was
identification
parameters,
in
which
imine
intermediate
formed
by
transient
halogenation
coupling
substitution
processes
underwent
either
aldol
condensation/annulation
or
hydrolysis/aldol
condensation.
additives
NH
4
Cl
Fe
(SO
)
unique
selectivity
this
reaction.
A
broad
substrate
scope
salicylaldehydes
employed
reaction,
demonstrating
excellent
functional
group
tolerance
versatility.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8521 - 8530
Опубликована: Июнь 3, 2024
An
oxidative
free-radical
C(sp2)–H
bond
chlorination
strategy
of
enaminones
has
been
developed
by
using
LiCl
as
a
chlorinating
reagent
and
K2S2O8
an
oxidant.
This
transformation
provides
new
straightforward
synthetic
methodology
to
afford
highly
functionalized
α-chlorinated
with
Z-configuration
in
good
excellent
yields.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(19), С. 13138 - 13153
Опубликована: Сен. 27, 2022
Electrochemical
synthesis
of
polysubstituted
sulfonated
pyrazoles
from
enaminones
and
sulfonyl
hydrazides
was
established
under
metal-free,
exogenous-oxidant-free,
mild
conditions.
By
judicious
choice
different
electrochemical
reaction
conditions,
NH2-functionalized
or
N,N-disubstituted
can
react
with
aryl/alkyl
to
afford
tetra-
trisubstituted
in
moderate
good
yields,
respectively.
The
gram-scale
transformation
demonstrated
the
efficiency
practicability
this
synthetic
strategy.
In
addition,
NH-pyrazole
be
obtained
via
dissociation
N-tosyl
group.
Mechanistic
studies
reveal
that
cascade
proceeded
sequence
intermolecular
condensation,
radical-radical
cross
coupling
sulfonylation,
pyrazole
annulation.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(21), С. 14957 - 14964
Опубликована: Окт. 19, 2022
The
Dess-Martin
periodinane
(DMP)
reagent-mediated
reactions
of
tertiary
enaminones
with
potassium
thiocyanate
for
the
synthesis
thiazole-5-carbaldehydes
are
developed.
product
formation
involves
cascade
hydroxyl
thiocyanation
C═C
double
bond,
intramolecular
hydroamination
C≡N
and
thiazole
annulation
by
condensation
on
ketone
carbonyl
site,
representing
novel
reaction
pathways
in
between
salt.
DMP
plays
dual
roles
mediating
free
radical
inducing
unconventional
selective
thiazole-5-carbaldehyde
masking
situ
generated
formyl
group
during
process.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(3), С. 1649 - 1664
Опубликована: Янв. 12, 2023
Isoflavones
were
synthesized
via
Suzuki–Miyaura
coupling
of
3-iodochromones
and
para-methoxybenzene-
para-phenolboronic
acid.
In
our
hands,
conditions
commonly
used
for
similar
cross
couplings
turned
out
to
be
unsuccessful
or
difficult
reproduce,
example,
due
the
unplanned
partial
cleavage
MOM-protecting
groups.
Using
Pd(dba)2
as
a
precatalyst
tricyclohexylphosphine
an
activating
ligand,
reliable
cross-coupling
identified.
all
cases,
notably
higher
yields
isoflavones
obtained
with
acid
than
para-methoxybenzene
boronic
This
observation
commercial
availability
suggest
that
synthesis
important
3′-prenyl-
3′,5′-diprenylisoflavone
substitution
pattern
synthetic
route
introduces
prenyl
substituents
after
Pd-catalyzed
step,
thereby
avoiding
laborious
protecting-group-intensive
multistep
syntheses
C-prenylated
arene
acids,
is
advantageous.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 216 - 223
Опубликована: Дек. 18, 2023
The
C–N
bond
transamidation
of
primary
amides
with
N,N-dimethyl
enaminones
has
been
efficiently
realized
by
heating
in
the
presence
trifluoromethanesulfonic
acid
(TfOH).
method
enables
practical
synthesis
valuable
enamides
without
use
any
metal
reagent.
In
addition,
this
protocol
can
also
be
expanded
to
reactions
sulfonamides,
and
late-stage
functionalization
on
sulfonamide
drugs
such
as
Celecoxib
Valdecoxib
verified.
Moreover,
participation
water
assisting
process
identified
isotope
labeling
experiments
using
D2O,
disclosing
a
new
possibility
designing
catalytic
tactic
other
reactions.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(9), С. 2607 - 2612
Опубликована: Янв. 1, 2024
A
metal-free,
scalable,
and
cascade
protocol
for
assembling
diverse
polysubstituted
pyridines
from
tertiary
enaminones
α,β-unsaturated
sulfonylketimines
by
cleaving
C–N/N–S
bonds
is
reported.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(28)
Опубликована: Май 1, 2024
Abstract
An
electrochemical
decarboxylative
addition
of
N
‐substituted
glycines
to
enaminones
has
been
developed
and
conducted
under
oxidant‐,
catalyst‐,
light‐free
conditions
in
acetonitrile
at
room
temperature
by
using
electron
as
the
traceless
oxidant,
which
provided
a
green
approach
access
C3‐aminomethyl
chromones.
The
resulting
products
were
formed
through
radical
addition/oxidation/cyclization
or
electrophilic
addition/cyclization
pathway
could
act
valuable
building
blocks
construct
polysubstituted
pyrimidine
derivatives.
