Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(38), С. 7821 - 7830
Опубликована: Янв. 1, 2023
A
new
approach
has
been
successfully
employed
to
synthesize
cyclic
ureas
via
carbonylation,
utilizing
Boc
anhydride
and
employing
K2CO3
as
a
base
along
with
N,N-dimethylformamide
the
solvent.
Remarkably
high
yields
were
achieved
using
in
conjunction
(Boc)2O,
enabling
streamlined
preparation
of
benzimidazolones
2-benzoxazolones
within
single
reaction
vessel.
Significantly,
this
obviates
necessity
for
any
dangerous
reagents,
rendering
it
environmentally
friendly,
its
key
benefit
lies
being
metal-free
system.
The
method
stands
out
efficiency,
concise
pathway,
optimization
from
readily
accessible
starting
materials,
ease
execution.
resulting
thoroughly
characterized
techniques
including
LCMS,
1H
NMR,
13C
NMR.
Organic Letters,
Год журнала:
2024,
Номер
26(15), С. 3014 - 3019
Опубликована: Март 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.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(6), С. 3857 - 3867
Опубликована: Фев. 22, 2024
In
the
present
study,
environment-friendly
visible-light-promoted
strategy
is
used
to
perform
an
efficient,
simple,
and
straightforward
photocatalytic
succinimide
derivative
synthesis
from
reaction
of
1,6-enynes
aryl
sulfonyl
bromide
at
room
temperature
under
air
ambient
conditions.
This
method
features
mild
conditions,
broad
substrate
scope,
high
yields,
excellent
configurational
selectivity.
addition,
all
atoms
substrates
involved
in
converge
product
structures,
showing
a
atomic
economy.
Moreover,
most
important
characteristic
this
study
that
no
photocatalyst
additives
are
used,
while
key
factor
triggers
visible
light,
indicating
has
practical
value.
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.
Herein,
we
report
a
visible
light-induced
difluoromethylation
cyclization
and
subsequent
amination-defluorination
reaction.
This
protocol
allows
efficient
to
valuable
3-fluoro-quinolinones
in
moderate
excellent
yields.
A
sequential
difluoromethylation-cyclization-amination-defluorination
mechanism
was
proposed
based
on
study.
Further
density
functional
theory
(DFT)
calculations
revealed
that
the
base
K
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.
Abstract
Synthesis
of
heterocyclic
compounds
is
fundamental
for
all
the
research
area
in
chemistry,
from
drug
synthesis
to
material
science.
In
this
framework,
catalysed
synthetic
methods
are
great
interest
effective
reach
such
important
building
blocks.
review,
we
will
report
on
some
selected
examples
last
five
years,
major
improvement
field,
focusing
most
conventional
catalytic
systems,
as
transition
metals,
organocatalysts,
more
sustainable
ones
photocatalysts,
iodine‐catalysed
reaction,
electrochemical
reactions
and
green
innovative
methods.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(21), С. 15374 - 15388
Опубликована: Окт. 23, 2023
We
report
an
organo-photocatalyzed
carboacylation
reaction
that
offers
a
springboard
to
create
chemical
complexity
in
diversity-driven
approach.
The
modular
one-pot
method
uses
feedstock
aldehydes
and
alcohols
as
acyl
surrogates
commercially
available
Eosin
Y
the
photoredox
catalyst,
making
it
simple
affordable
introduce
structural
diversity.
Several
biologically
relevant
skeletons
have
been
easily
synthesized
under
mild
conditions
presence
of
visible
light
irradiation
by
fostering
radical
acylation/cyclization
cascade.
proposed
mechanism
was
further
illuminated
number
spectroscopic
studies.
Furthermore,
we
applied
this
protocol
for
late-stage
functionalization
pharmaceuticals
blockbuster
drugs.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
22(1), С. 10 - 24
Опубликована: Ноя. 23, 2023
In
this
review,
we
conclude
recent
main
themes
in
trapping
SO
2
,
CO
or
O
by
cyanoalkyl
radicals,
which
are
produced
from
iminyl-radical-triggered
C–C
bond
cleavage
of
cyclobutanone
oxime
derivatives.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(8), С. 5328 - 5336
Опубликована: Апрель 10, 2024
The
thiazole-2-imine
derivatives
with
interesting
pharmacological
activities
have
attracted
significant
attention.
However,
previously
reported
synthesis
strategies
usually
suffered
from
some
drawbacks,
such
as
the
use
of
metals/additive
and
harsh
reaction
conditions.
Herein,
we
developed
a
metal-
photoinitiator-free
photocatalytic
strategy
for
various
selenium-substituted
first
time.
displayed
mild
conditions,
simple
operation,
broad
substrate
scope
(37
examples),
good
to
excellent
yields.
