γ-Butyrolactone Synthesis from Allylic Alcohols Using the CO2 Radical Anion
Precision Chemistry,
Год журнала:
2024,
Номер
2(3), С. 88 - 95
Опубликована: Фев. 16, 2024
γ-Butyrolactone
structures
are
commonly
found
in
various
natural
products
and
serve
as
crucial
building
blocks
organic
synthesis.
Consequently,
the
development
of
methods
for
synthesizing
γ-butyrolactones
has
garnered
significant
interest
within
synthesis
community.
In
this
study,
we
present
a
direct
highly
efficient
approach
from
allylic
alcohols.
Notably,
study
represents
first
instance
γ-butyrolactone
initiated
by
radical
hydrocarboxylation
using
CO2•–,
generated
metal
formates,
followed
cyclization.
This
two-step
process
is
achieved
through
synergistic
interaction
photoredox
hydrogen
atom
transfer
(HAT)
catalysis,
resulting
production
with
exceptional
efficiency.
Additionally,
when
employing
α,α-diaryl
alcohol
derivatives
substrates,
reaction
involves
1,2-aryl
migration,
which
occurs
concomitantly
CO2•–
addition,
leading
to
formation
4,5-substituted
lactones
good
yield.
The
artificial
force
induced
(AFIR)
method
identified
preferred
migration
pathway
along
potential
byproduct
pathways,
targeted
1,2-migration
was
be
most
plausible
pathway.
Язык: Английский
Copper-catalyzed trichloromethylative carbonylation of ethylene
Chemical Science,
Год журнала:
2023,
Номер
15(4), С. 1418 - 1423
Опубликована: Дек. 14, 2023
Difunctionalization
of
alkenes
is
an
efficient
strategy
for
the
synthesis
complex
compounds
from
readily
available
starting
materials.
Herein,
we
developed
a
copper-catalyzed
visible-light-mediated
trichloromethylative
carbonylation
ethylene
by
employing
commercially
CCl
Язык: Английский
Metal-free polychloromethylation/cyclization of unactivated alkenes towards ring-fused tricyclic indolones and benzoimidazoles
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(35), С. 7079 - 7084
Опубликована: Янв. 1, 2023
Polychloromethylative
cyclization
of
N-alkenyl
indoles
was
developed
under
metal-free
conditions
to
afford
tricyclic
pyridoindolones
and
pyrroloindolones
in
moderate
good
yields.
In
the
reaction,
commercially
available
CHCl3
CH2Cl2
were
employed
as
tri-
dichloromethyl
radical
sources.
Moreover,
dichloromethylated
polycyclic
benzoimidazoles
can
also
be
obtained
standard
conditions.
Язык: Английский
Decennary Update on Oxidative‐Rearrangement Involving 1,2‐Aryl C‐C Migration Around Alkenes: Synthetic and Mechanistic Insights
Chemistry - An Asian Journal,
Год журнала:
2024,
Номер
19(14)
Опубликована: Май 14, 2024
In
recent
years,
numerous
methodologies
on
oxidative
rearrangements
of
alkenes
have
been
investigated,
that
produce
multipurpose
synthons
and
heterocyclic
scaffolds
potential
applications.
The
present
review
focused
recently
established
for
transformation
via
1,2-aryl
migration
in
(2013-2023).
Special
emphasis
has
placed
mechanistic
pathways
to
understand
the
reactivity
pattern
different
substrates,
challenges
enhance
selectivity,
key
role
reagents,
effect
substituents,
how
they
affect
rearrangement
process.
Moreover,
synthetic
limitations
future
direction
also
discussed.
We
believe,
this
offers
new
insight
develop
elegant
precursors
approaches
explore
utilization
alkene-based
compounds
natural
product
synthesis
functional
materials.
Язык: Английский
Visible‐Light‐Mediated Oxidative Desulfurization‐Oxygenation in Cyclic Thio‐Amide
ChemistrySelect,
Год журнала:
2024,
Номер
9(18)
Опубликована: Май 6, 2024
Abstract
Visible‐light
assisted
a
very
simple
and
mild
protocol
for
photocatalytic
oxidative
transformation
of
thioamide
to
amide
group
has
been
realized
in
cyclic
system.
For
this
purpose
5‐arylalkylidene‐rhodanine
derivatives
were
chosen
as
model
substrates
afford
thiazolidine‐2,4‐diones.
Light
mediated
reactions
are
intrinsically
beneficial,
since
activation
occurs
by
cleanest
energy
source
light.
Here
K
2
S
O
8
is
used
terminal
oxidant
which
does
not
leave
any
hazardous
corrosive
waste
discard
after
the
reaction
fostering
practices
green
chemistry.
This
first
report
conversion
thioxo
rhodanine
into
corresponding
oxygen
analogue
visible
light
photo‐catalytic
method.
The
was
general
various
5‐arylalkylidene‐rhodanines
underwent
smoothly
affording
high
product
yields.
Moreover,
broadness
further
established
applying
on
other
systems
like
3,4‐dihydropyrimidine‐2(1H)‐(thio)ones.
Язык: Английский
Photoredox Polychloroalkylation/Spirocyclization of Activated Alkynes via C(sp3)‐H bond Cleavage
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
27(6)
Опубликована: Дек. 11, 2023
Abstract
A
novel
strategy
of
visible‐light
photoredox
catalysis
ipso
‐annulation
activated
alkynes
with
polychloroalkanes
for
the
synthesis
3‐polychloroalkyl
spiro[4,5]trienones,
which
used
4‐methoxybenzenediazonium
tetrafluoroborate
salt
as
a
hydrogen
atom
transfer
reagent,
is
described.
This
polychloroalkylation/
spirocyclization
offers
widely
range
3‐polychloroalkyl‐spiro[4,5]trienone
derivatives
in
high
yields
broad
substrate
scope
via
selective
C(sp
3
)‐H
homolytic
cleavage.
The
results
controlled
experiments
showed
that
this
method
involves
radical
process.
polyhaloalkyl
species
generated
from
intermolecular
(HAT)
between
aryl
and
polychloroalkanes.
Язык: Английский
Synthesis of 4-(trichloromethyl)pyrido[2′,1′:3,4]pyrazino[2,1-b]quinazolinones through a cyclized dearomatization and trichloromethylation cascade strategy
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(7), С. 1386 - 1390
Опубликована: Янв. 1, 2024
An
intramolecular
6-
endo-dig
cyclization
and
trichloromethylation
of
N
3-alkynyl-2-pyridinyl-tethered
quinazolinones
in
chloroform
was
developed
for
the
synthesis
various
4-trichloromethylated
pyrido-fused
moderate
to
good
yields
with
high
regioselectivity.
Язык: Английский
Photocatalytic Hydrodichloromethylation of Unactivated Alkenes with Chloroform
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 16, 2024
A
visible-light-induced
method
for
the
hydrodichloromethylation
of
unactivated
alkenes
using
chloroform
(CHCl3)
was
developed,
employing
pyridine·BH3
as
halogen
atom
transfer
(XAT)
reagent.
The
strategy
showed
a
broad
functional
group
tolerance,
and
29
examples
alkenes,
including
complex
natural
products
or
drug
derivatives,
have
been
established
with
good
yields.
Mechanistic
studies
indicated
that
CHCl3
serves
both
source
dichloromethyl
radical
hydrogen
(HAT)
reagent,
borane
short-chain
reaction
process
involved
in
this
system.
This
represents
novel
approach
without
an
additional
HAT
Язык: Английский