The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2741 - 2747
Опубликована: Фев. 1, 2024
Acyl
radicals
have
been
generated
from
the
decarboxylation
of
α-oxocarboxylic
acids
by
using
a
readily
accessible
organic
pyrimidopteridine
photoredox
catalyst
under
ultraviolet-A
(UV-A)
light
irradiation.
These
reactive
acyl
were
smoothly
added
to
olefins
such
as
styrenes
and
diverse
Michael
acceptors,
with
assistance
H2O/D2O
hydrogen
donors,
enabling
easy
access
range
ketones/β-deuterio
ketones.
A
wide
are
compatible
this
reaction,
which
shows
reliable,
atom-economical,
eco-friendly
protocol.
Furthermore,
postsynthetic
diversifications
applications
presented.
Chemical Society Reviews,
Год журнала:
2022,
Номер
51(4), С. 1415 - 1453
Опубликована: Янв. 1, 2022
This
review
summarizes
recent
progress
on
using
carboxylic
acids
directly
as
convenient
precursors
for
the
1,4-radical
conjugate
addition
(Giese)
reaction.
Journal of the American Chemical Society,
Год журнала:
2022,
Номер
144(37), С. 17261 - 17268
Опубликована: Сен. 7, 2022
Direct
CAr-F
arylation
is
effective
and
sustainable
for
synthesis
of
polyfluorobiaryls
with
different
degrees
fluorination,
which
are
important
motifs
in
medical
material
chemistry.
However,
no
aid
transition
metals,
the
engagement
bond
activation
has
proved
difficult.
Herein,
an
unprecedented
transition-metal-free
strategy
reported
site-selective
polyfluoroarenes
simple
(het)arenes.
By
merging
N,N-bis(2,6-diisopropylphenyl)perylene-3,4,9,10-bis(dicarboximide)-catalyzed
electrophotocatalytic
reduction
anodic
nitroxyl
radical
oxidation
cell,
various
polyfluoroaromatics
(2F-6F
8F),
especially
inactive
partially
fluorinated
aromatics,
undergo
sacrificial-reagents-free
C-F
high
regioselectivity,
yields
comparable
to
those
transition-metal
catalysis.
This
atom-
step-economic
protocol
features
a
paired
electrocatalysis
organic
mediators
both
cathodic
processes.
The
broad
substrate
scope
good
functional-group
compatibility
highlight
merits
this
operationally
strategy.
Moreover,
easy
gram-scale
late-stage
functionalization
collectively
advocate
practical
value,
would
promote
vigorous
development
fluorine
Chemical Science,
Год журнала:
2022,
Номер
13(24), С. 7256 - 7263
Опубликована: Янв. 1, 2022
Various
commercially
available
acyl
chlorides,
aldehydes,
and
alkanes
were
exploited
for
versatile
three-component
1,2-carboacylations
of
alkenes
to
forge
two
vicinal
C-C
bonds
through
the
cooperative
action
nickel
sodium
decatungstate
catalysis.
A
wealth
ketones
with
high
levels
structural
complexity
was
rapidly
obtained
via
direct
functionalization
C(sp2)/C(sp3)-H
in
a
modular
manner.
Furthermore,
regioselective
late-stage
modification
natural
products
showcased
practical
utility
strategy,
generally
featuring
resource
economy
ample
substrate
scope.
ACS Catalysis,
Год журнала:
2022,
Номер
12(3), С. 1879 - 1885
Опубликована: Янв. 20, 2022
Transition-metal-catalyzed
cross-coupling
reactions
are
a
powerful
tool
to
construct
carbon–carbon
bonds
in
modern
synthetic
chemistry.
Chromium
catalysis
is
much
less
developed
compared
with
the
widely
used
palladium
and
nickel
catalysis.
Herein,
we
reported
an
efficient
flexible
chromium-catalyzed
radical
diacylation
of
alkenes
help
visible-light
photoredox
catalysis,
giving
access
valuable
1,4-,
1,6-,
1,7-diones
under
mild
conditions.
The
utility
this
methodology
was
proven
by
converting
diones
diverse
heterocycles.
Furthermore,
same
dual
system
can
be
successfully
applied
dienes
vinyl
cyclopropanes.
A
possible
mechanism
alkene
via
photoredox/chromium
proposed
according
control
experiments
DFT
calculations.
Organic Letters,
Год журнала:
2022,
Номер
24(32), С. 6018 - 6023
Опубликована: Авг. 10, 2022
We
disclosed
herein
a
straightforward
photochemical
method
for
the
construction
of
phenanthridines
containing
synthetically
useful
succinate
unit.
The
reaction
occurred
under
visible-light
irradiation
with
cheap
eosin
Y
Na
as
photoredox
catalyst
and
diazo
compound
precursor.
Under
optimal
conditions,
wide
range
were
obtained
in
moderate
to
good
yields.
Note
that
units
final
heterocycles
could
be
easily
transformed
into
many
valuable
structures,
such
γ-butyrolactone,
dihydrofuran-2(3H)-one,
tetrahydrofuran.
Mechanistic
experiments
performed
support
proposed
mechanism.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(18), С. 4488 - 4515
Опубликована: Янв. 1, 2023
This
review
highlights
the
recent
advances
in
radical
acylated
difunctionalization
of
unsaturated
carbon–carbon
bonds
and
focuses
on
mechanistic
insights
these
transformations.
Organic Letters,
Год журнала:
2023,
Номер
25(13), С. 2372 - 2376
Опубликована: Март 27, 2023
A
novel
trifluoromethylation
of
(hetero)arenes
and
polarized
alkenes
using
simple
trifluoroacetic
anhydride
(TFAA)
as
the
low
price
CF3
source
under
photoredox
catalysis
was
developed
without
additives
such
bases,
hyperstoichiometric
oxidant,
or
auxiliaries.
The
reaction
showed
excellent
tolerance,
including
to
some
important
natural
products
prodrugs,
even
on
gram
scale
extended
ketones.
This
protocol
provides
a
practical
utilization
TFAA.
Several
perfluoroalkylations
trifluoromethylation/cyclizations
were
successfully
achieved
identical
conditions.
ACS Catalysis,
Год журнала:
2022,
Номер
12(20), С. 12984 - 12992
Опубликована: Окт. 12, 2022
The
synthesis
of
chiral
ketones
has
been
a
long
focus
chemistry
research.
Enantioselective
radical
hydroacylation,
as
useful
strategy
to
access
various
ketones,
was
restricted
the
reaction
with
β-substituted
alkenes,
in
which
β-stereocenter
generated
via
stereocontrolled
addition
prochiral
alkene.
Herein,
we
realized
highly
enantioselective
hydroacylation
α-substituted
α,β-unsaturated
carbonyl
compounds
through
direct
hydrogen
atom
transfer
presence
photocatalyst
anthraquinone
and
N,N′-dioxide/metal
complexes.
This
mild,
robust
method
provided
facile
wide
array
α-tertiary
stereocenters
by
using
readily
available
aldehyde
reagent.
Based
on
spectroscopy
experiments
control
together
DFT
calculations,
transfer/radical
addition/enantioselective
reverse
sequence
proposed.
