Copper-Catalyzed Radical Relay 1,3-Carbocarbonylation across Two Distinct C═C Bonds
Nan‐Nan Dai,
No information about this author
Yue-Jiao Lu,
No information about this author
Zhong-Qi Wu
No information about this author
et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3014 - 3019
Published: March 28, 2024
The
radical
relay
provides
an
effective
paradigm
for
intermolecular
assembly
to
achieve
functionalization
across
remote
chemical
bonds.
Herein,
we
report
the
first
1,3-carbocarbonylation
of
α-carbonyl
alkyl
bromides
two
separate
C═C
reaction
is
highly
chemo-
and
regioselective,
with
C(sp3)–C(sp3)
bonds
one
C═O
bond
formed
in
a
single
orchestrated
operation.
In
addition,
synthesis
method
under
mild
conditions
using
inexpensive
copper
as
catalyst
allows
facile
access
structurally
diverse
products.
plausible
mechanism
investigated
through
series
control
experiments,
including
trapping,
clock
critical
intermediate
18O
labeling
experiment.
Language: Английский
Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles
Beilstein Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
21, P. 234 - 241
Published: Jan. 30, 2025
An
efficient
and
eco-friendly
approach
for
synthesizing
difluoromethyl-
aryldifluoromethyl-substituted
polycyclic
imidazoles
was
established
via
a
visible-light-promoted
radical
cyclization
reaction.
This
method
employed
the
readily
accessible
inexpensive
CF
2
HCO
H
or
PhCF
COOH,
along
with
benzimidazoles
bearing
unactivated
alkenes
PhI(OAc)
as
substrates,
proceeded
without
need
of
any
base,
metal
catalyst,
photocatalyst
additive.
In
total,
24
examples
were
examined,
all
them
successfully
underwent
reaction
to
produce
target
products
in
good
excellent
yields.
Mechanistic
studies
revealed
that
proceeds
pathway.
Language: Английский
Visible-light-induced decarboxylative cascade cyclization of acryloylbenzamides with N-hydroxyphthalimide esters via EDA complexes
Qing Li,
No information about this author
Zhi‐Qiang Zhu,
No information about this author
Wenyi Zhang
No information about this author
et al.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(5), P. 965 - 969
Published: Jan. 1, 2024
A
visible-light-induced,
electron
donor–acceptor
(EDA)
complex-enabled
decarboxylative
cascade
reaction
of
acryloylbenzamides
with
alkyl
N
-hydroxyphthalimide
esters
by
NaI/PPh
3
catalysis
was
developed.
Language: Английский
Pentafluorosulfanylation of Acrylamides: The Synthesis of SF5-Containing Isoquinolinediones with SF5Cl
Xinqiang Tan,
No information about this author
Yuezhen Li,
No information about this author
Ziyou Hao
No information about this author
et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(21), P. 15941 - 15952
Published: Oct. 24, 2024
We
disclose
herein
an
efficient
and
facile
method
for
the
synthesis
of
SF5-containing
isoquinolinediones
with
all-carbon
quaternary
stereocenter
via
intramolecular
pentafluorosulfanylation
acrylamides
using
SF5Cl
as
a
reagent.
The
protocol
proceeds
under
mild
reaction
conditions
enjoys
broad
substrate
scope,
wide
functional
group
compatibility,
high
atom-
step-economy.
A
radical
mechanism
involving
SF5
cascade
addition/cyclization
is
proposed.
Language: Английский
Recent developments for the synthesis of the dihydroisoquinolin-1(2H)-ones via cyclization of N-allylbenzamides
Tetrahedron,
Journal Year:
2025,
Volume and Issue:
unknown, P. 134497 - 134497
Published: Jan. 1, 2025
Language: Английский
Photocatalytic Proton-Coupled Electron Transfer Enabled Radical Cyclization for Isoquinoline-1,3-diones Synthesis
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(7), P. 5060 - 5068
Published: March 25, 2024
Radical
cyclization
has
been
demonstrated
to
be
an
efficient
method
access
functionalized
heterocycles
from
easily
accessible
raw
materials.
Described
herein
is
the
development
of
a
photocatalytic
proton-coupled
electron
transfer
(PCET)
strategy
for
synthesis
isoquinoline-1,3-diones
using
readily
prepared
naphthalimide
(NI)-based
organic
photocatalysts.
The
process
features
free
metal-complex
photocatalysts,
acids,
and
mild
reaction
conditions.
This
radical
protocol
broad
substrate
scope
can
effectively
applied
variety
medicinally
relevant
substrates.
Furthermore,
control
experiments
were
conducted
elucidate
mechanism
this
visible
light-induced
methodology.
Language: Английский
Copper-Catalyzed Trifluoromethylthiolaton and Radical Cyclization of N-Phenylpent-4-Enamides to Construct SCF3-Substituted γ-Lactams
Catalysts,
Journal Year:
2024,
Volume and Issue:
14(11), P. 797 - 797
Published: Nov. 7, 2024
An
efficient
method
involving
copper-catalyzed
trifluoromethylthiolation
and
radical
cyclization
of
N-phenylpent-4-enamides
using
readily
available
stable
AgSCF3
as
the
trifluoromethylthiolating
reagent
is
described.
The
enables
synthesis
a
series
potential
medicinally
valuable
trifluoromethylthio-substituted
γ-lactams
relative
2-oxazolidinone
derivatives
with
broad
functional
group
compatibility.
Mechanistic
investigations
indicated
that
this
reaction
involved
amidyl
radical-initiated
cascade
5-exo-trig
followed
by
trifluoromethylthiolation,
resulting
in
formation
new
C-N
C-S
bonds.
Language: Английский