Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(24), С. 4513 - 4519
Опубликована: Окт. 31, 2023
Abstract
An
oxidant‐free
photocatalytic
[2+2+m]
cyclization
of
2‐cyanoaryl
acrylamides
with
2‐bromocarbonyls
is
reported,
enabling
the
assembly
biologically
important
N‐heterocycle‐fused
quinolinones
including
benzo[1,6]naphthyridinones
and
pyrrolo[3,2‐
c
]‐quinolines.
This
protocol
proceeds
through
a
radical
relay
pathway
alkene
difunctionalization
along
an
intramolecular
cyano
insertion
subsequent
site‐specific
functionalization
inert
C(
sp
3
)−H
bond
enabled
by
cyano‐derived
iminyl
radical‐mediated
1,n‐hydrogen
atom
transfer.
Notably,
this
transformation
selectively
formed
two
distinct
C−C
bonds,
one
C−N
bond,
quaternary
carbon
center
in
one‐pot
procedure.
Organic Letters,
Год журнала:
2025,
Номер
27(4), С. 1030 - 1035
Опубликована: Янв. 20, 2025
Compared
with
the
energetically
favorable
5-
or
6-membered
fluoro-functionalized
heterocycles,
construction
of
medium-sized
fluoro-heterocycles
is
relatively
under-researched
because
their
inherently
unfavorable
enthalpic
and
entropic
nature.
Based
on
rational
design
DFT
calculations,
a
novel
photocatalytic
difluoromethyl
radical-initiated
intramolecular
7-endo-trig
cyclization
was
realized,
thus
affording
sustainable
route
for
synthesis
challenging
N-heterocycles.
Depending
atomic
dipole
moment
corrected
Hirshfeld
population
(ADCH)
charge
chemoselective
6-exo-trig
radical
cyclizations
were
further
replenished.
Large-scale
derivatization
demonstrated
wide
utility
this
method.
Chemical Communications,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
We
report
a
novel
visible-light-induced
sulfonylation
cyclization
and
aerobic
selenylation
reaction
for
the
rapid
construction
of
highly
functionalized
indole-fused
medium-sized
diazepinones
with
biomass
feedstock
2-Me-THF
as
medium.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 27, 2025
A
novel
visible-light-induced
sulfonylation
cyclization
to
indole-fused
medium-sized
N-heterocycles
was
established
under
room
temperature
with
biomass-derived
2-Me-THF
as
the
solvent.
This
reaction
proceeds
in
absence
of
external
photocatalyst,
additive,
metal
salts,
and
base.
Broad
substrate
scope,
good
functional
group
compatibility,
large-scale
synthesis
derivatization
via
iodination,
nitration,
chlorination,
cyanation,
selenylation
demonstrate
utility
this
protocol.
radical
route
proposed
based
on
inhibition
experiments,
visible-light
irradiation
on-off
test,
apparent
quantum
efficiency
calculation,
UV-vis
absorption
spectroscopic
studies.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(22), С. 15969 - 15974
Опубликована: Окт. 30, 2023
Described
herein
is
a
photoinduced
copper-catalyzed
1,2-difunctionalization
of
1,3-dienes.
The
selenium
atom
radical
was
generated
by
the
visible
light
irradiation
diselenides,
triggering
addition
with
1,3-dienes
to
form
allyl
intermediate.
Subsequent
rapid
Z/E
isomerization
allowed
for
thermodynamically
favorable
intermediate
formation
and
enabled
copper
catalyzed
stereoselective
functionalization
various
nucleophiles.
Organic Letters,
Год журнала:
2024,
Номер
26(3), С. 757 - 762
Опубликована: Янв. 17, 2024
A
dual
nickel-
and
iridium-photocatalyzed
radical
cascade
bicyclization
reaction
for
the
synthesis
of
highly
complex
molecular
structures
in
an
atom-
step-economic
manner
has
been
described.
series
precursors
are
utilized
divergent
diversely
substituted
fluorenes
indenoazepinones
bearing
quaternary
carbons
by
using
cyclization
reactions
1,5-enynes.
This
is
characterized
its
mild
conditions,
broad
substrate
scope,
excellent
selectivity,
satisfactory
yield
including
facile
scale-up
synthesis.
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
13(4)
Опубликована: Фев. 26, 2024
Abstract
A
convenient
visible–light–promoted
phosphorylation
reaction
of
α‐diazoesters
with
H‐phosphine
oxides
for
the
preparation
(
Z
)‐phosphinic
hydrazones
has
been
explored.
This
could
be
performed
under
mild
conditions
to
afford
a
series
in
moderate
good
yields
through
photoisomerization
C=N
bond.
A
100%
atom
economical
construction
of
hydroxyalkylated
N-heteroarenes
through
decatungstate-catalyzed
tandem
cyclization/self-hydrogenation
isocyanides
and
aldehydes
under
exogenous
hydrogen
reagent-
byproduct-free
conditions
was
developed.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(27)
Опубликована: Март 11, 2024
A
visible-light-induced
strategy
has
been
explored
for
the
synthesis
of
naphtho[2,1-d]thiazol-2-amines
through
ortho-C-H
sulfuration
2-isocyanonaphthalenes
with
elemental
sulfur
and
amines
under
external
photocatalyst-free
conditions.
This
three-component
reaction,
which
utilizes
as
odorless
source,
molecular
oxygen
clean
oxidant,
visible
light
energy
provides
a
mild
efficient
approach
to
construct
series
naphtho[2,1-d]thiazol-2-amines.
Preliminary
mechanistic
studies
indicated
that
visible-light-promoted
photoexcitation
reaction
intermediates
consisting
thioureas
DBU
might
be
involved
in
this
transformation.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(17)
Опубликована: Март 11, 2024
Abstract
Molecules
containing
ether
skeletons
are
widely
present
in
drugs,
natural
products,
functional
materials,
and
life
science.
Direct
C(sp
3
)−H
bond
functionalization
is
considered
a
powerful
strategy
for
the
construction
of
novel
derivatives.
Photo‐/electro‐chemical
technology
relatively
green
sustainable
synthesis
method,
which
opens
up
broad
application
prospect
field
direct
bonds.
In
recent
years,
photo‐/electro‐mediated
alkylation,
arylation,
alkynylation,
esterification,
mercaptoylation,
sulfidation,
amination
ethers
have
been
extensively
studied.
this
review,
research
progress
compounds
from
2014
to
2023
systematically
reviewed,
scope,
limitations,
mechanisms
some
reactions
discussed.
