Abstract
A
computational
study
on
the
reaction
mechanism
of
effective
synthesis
sulfonated
benzo[
b
]oxepinones
and
chromanes
by
radical
cascade
cyclization
is
carried
out
employing
density
functional
theory
(DFT).
Based
our
computations,
rate‐determining
step
formation
arylsulfonyl
for
scheme.
Our
calculations
show
that
1,8‐
1,7‐enynes
with
proceeds
forming
more
thermodynamically
stable
intermediates.
Therefore,
1,8‐enynes
prefer
7‐
exo
‐trig
cyclization,
while
6‐
cyclization.
computations
are
consistent
experimental
results
1,7‐enynes.
Moreover,
if
in
a
proton‐free
solvent,
elimination
product
can
be
obtained
from
1,7‐enyne.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(15), С. 10614 - 10623
Опубликована: Июль 25, 2024
A
photocatalyst-free
and
EDA
complex-enabled
radical
cascade
cyclization
reaction
of
inactive
alkenes
with
bromodifluoroacetamides
was
reported
for
the
divergent
synthesis
fluorine-containing
tetralones
quinazolinones.
In
this
transformation,
persulfates
as
electron
donors
difluoro
bromamide
acceptors
generate
complex.
This
is
a
promising
photochemical
method
advantages
such
mild
conditions,
simple
operation,
being
metal-free,
excellent
functional
group
tolerance.
Organic Letters,
Год журнала:
2023,
Номер
25(32), С. 6072 - 6076
Опубликована: Авг. 8, 2023
A
novel
and
efficient
strategy
for
the
synthesis
of
a
series
structurally
interesting
benzazepine
derivatives
via
an
N-heterocyclic
carbene-catalyzed
regioselective
intramolecular
radical
cyclization
has
been
developed.
This
protocol
features
good
regioselectivity,
functional-group
compatibility,
wide
substrate
scope,
providing
transition-metal-
oxidant-free
pathway
to
access
seven-membered
rings
under
mild
reaction
conditions.
Additionally,
further
transformation
benzazepines
large-scale
experiment
were
also
conducted.
Chemical Communications,
Год журнала:
2024,
Номер
60(36), С. 4834 - 4837
Опубликована: Янв. 1, 2024
A
convenient
method
for
oxidant-promoted
radical
cascade
acylation
or
decarbonylative
alkylation
of
1,7-dienes
with
aldehydes
the
construction
tetracyclic
N-containing
skeletons
has
been
established.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2238 - 2246
Опубликована: Янв. 31, 2024
Visible-light-induced
regioselective
cascade
radical
cyclization
of
α-bromocarbonyls
for
the
synthesis
benzazepine
derivatives
is
described.
In
presence
fac-Ir(ppy)3
(2.0
mol
%)
as
a
photocatalyst,
2,6-lutidine
base,
and
dichloromethane
solvent,
reactions
proceed
smoothly
to
afford
seven-membered
rings
in
good
yields.
This
protocol
features
broad
substrate
scope,
excellent
functional
group
tolerance,
mild
reaction
conditions.
Preliminary
mechanistic
studies
reveal
that
generation
α-carbon
more
prone
react
with
1,1-diphenylethylene
tethered
acrylamide
generate
stable
heterocycle.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(8), С. 1833 - 1839
Опубликована: Фев. 8, 2024
Abstract
Herein,
we
report
a
photochemical
synthesis
of
1,4‐dicarbonyl
containing
quinoxalin‐2(1
H
)‐ones
through
consecutive
photoredox
catalysed
reactions.
A
wide
range
C3‐modified
were
obtained
in
53–91%
yields
by
this
approach.
Mechanistic
studies
including
radical
trapping,
EPR
studies,
D‐labelling
investigations,
and
many
other
control
experiments
well
explained
the
proposed
mechanism.
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 19, 2025
Comprehensive
Summary
This
study
presents
an
efficient
and
innovative
allylation
strategy
utilizing
C/N/O
nucleophilic
reagents
with
attenuated
reactivity,
enabling
the
construction
of
versatile
allyl
compounds.
The
approach
focuses
on
sequential
dihalides
in
large‐scale
chemical
manufacturing,
effectively
addressing
challenge
achieving
selectivity
cascade
reactions.
methodology
is
centered
Cu‐catalyzed
C
‐olefination
alkynes
dihalides,
significantly
expediting
synthesis
a
diverse
array
finely
conjugated
enyne
derivatives.
Furthermore,
base‐facilitated
condensation
process
has
been
developed
to
achieve
N
‐allylation
hydrazines,
yielding
wide
range
trisubstituted
alkenyl
hydrazones.
Additionally,
protocol
enables
high‐value
ester
compounds
through
O
or
esterification
dihalides.
transformation
also
facilitates
one‐step
variety
essential
pharmaceuticals,
demonstrating
its
broad
synthetic
utility
potential.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 152 - 162
Опубликована: Дек. 12, 2023
Reactions
with
diverse
C1
synthons
to
realize
homologation
were
well
explored.
However,
homologations
occurring
twice
one
synthon
in
a
reaction
less
reported.
We
disclose
herein
Cu(II)-catalyzed
novel
and
efficient
synthesis
of
2H-chromenes
from
2-naphthols,
1,3-diketones,
N,N-dimethylethanolamine
(DMEA)
as
dual
carbon
synthon.
Various
different
functional
groups
are
constructed
moderate
good
yields.
This
is
the
first
report
that
DMEA
acts
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(19), С. 2323 - 2328
Опубликована: Май 22, 2024
Comprehensive
Summary
A
novel
visible‐light‐induced
radical
cascade
6‐
endo
cyclization
of
dienes
(
N
‐(2‐vinylphenyl)acryl
amides)
is
developed
utilizing
α‐carbonyl
bromides
as
alkyl
reagents.
This
approach
affords
an
efficient
way
for
synthesizing
six‐membered
benzo‐fused
lactam
derivatives
with
chemo‐
and
regio‐selectivity
good
functional
group
tolerance.
Primary,
secondary,
tertiary
are
well‐compatible
this
reaction.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(13), С. 3313 - 3320
Опубликована: Янв. 1, 2023
A
novel
light
induced
8-endo
sulfonyl
cyclization
to
medium-sized
benzo[
b
]azocines
is
developed.
DFT
calculations
rationalize
the
rate-determining
step
and
chemoselectivity
observed
in
this
transformation.
