ACS Catalysis,
Год журнала:
2024,
Номер
unknown, С. 17642 - 17653
Опубликована: Ноя. 15, 2024
The
combination
of
N-heterocyclic
carbene
(NHC)
organocatalysis
with
photochemical
activation
is
becoming
increasingly
established
as
an
approach
for
conducting
radical
organic
reactions
under
mild
and
practical
conditions.
As
comparatively
easy
to
prepare
handle
compounds,
alkyl
silanes
are
attractive
substrates
chemistry
desilylative
mesolysis
the
corresponding
cations
known
be
rapid.
Here,
we
report
successful
application
benzyl
silane
derivatives
source
radicals
in
dual
NHC/photoredox-catalyzed
radical–radical
coupling
acyl
fluorides.
Relatively
electron-rich
reacted
smoothly
afford
ketones
generally
good
yields,
while
optimization
NHC
photocatalyst
allowed
a
wider
scope
including
primary
substrates.
Furthermore,
initial
experiments
revealed
that
organosilanes
bearing
N-,
O-
S-heteroatoms
can
also
serve
sources
these
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(32), С. 22829 - 22839
Опубликована: Авг. 1, 2024
The
molecular
editing
of
ketones
represents
an
appealing
strategy
due
to
its
ability
maximize
the
structural
diversity
ketone
compounds
in
a
straightforward
manner.
However,
developing
efficient
methods
for
arbitrary
modification
ketonic
molecules,
particularly
those
integrated
within
complex
skeletons,
remains
significant
challenge.
Herein,
we
present
unique
recasting
that
involves
radical
acylation
Organic Letters,
Год журнала:
2024,
Номер
26(32), С. 6915 - 6920
Опубликована: Авг. 8, 2024
Ketones,
as
essential
functional
group
skeletons,
have
garnered
significant
interest
due
to
their
diverse
transformations.
Herein,
we
describe
a
versatile
photoredox
catalyzed
deacylation-aroylation
strategy
that
enables
the
direct
transformation
of
alkyl
ketones
aryl
ketones.
This
process
involves
deacylation
dihydroquinazolinones
derived
from
generate
radicals,
followed
by
subsequent
NHC-catalyzed
or
NHC-mediated
radical
aroylation.
ACS Catalysis,
Год журнала:
2025,
Номер
15(2), С. 1287 - 1293
Опубликована: Янв. 7, 2025
C(sp3)–H
bond
functionalization
is
a
powerful
strategy
for
the
synthesis
of
organic
compounds
due
their
abundance
in
simple
starting
materials.
Photoredox
catalysis
has
led
to
diverse
array
enabling
activation
strategies;
however,
general
platform
direct
carboxylic
acid
derivatives
remains
elusive.
Disclosed
herein
development
cooperative
NHC/photoredox-catalyzed
esterification
transformation.
This
method
enables
access
benzylic,
α-heteroatom,
and
formal
β-esterification
products
moderate
high
yields
under
mild
reaction
conditions.
ACS Catalysis,
Год журнала:
2025,
Номер
15(3), С. 1973 - 2001
Опубликована: Янв. 20, 2025
Chiral
quaternary
ammonium
ion-pair
organocatalysis
has
been
widely
used
in
the
facile
synthesis
of
chiral
molecules
with
challenging
stereocenters.
Especially,
numerous
asymmetric
nucleophilic
addition
reactions
have
facilitated
this
strategy.
This
review
systematically
summarizes
additions
promoted
by
salts
past
decade.
The
content
is
organized
according
to
types
electrophiles
involved
these
catalytic
transformations.
Our
own
perspectives
on
future
development
within
highly
active
research
field
are
also
provided.
Advanced Synthesis & Catalysis,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 23, 2025
Abstract
Imidazolium‐dithiocarboxylate
zwitterions
(NHC
⋅
CS
2
),
a
novel
organocatalyst
that
derived
from
N‐heterocyclic
carbene
(NHC),
was
used
to
activate
cyclopropenones.
Under
the
catalysis
of
10
mol%
NHC
2,
range
phenols,
alcohols,
primary
and
secondary
amines
react
with
cyclopropenones
produce
trisubstituted
α
,
β
‐unsaturated
esters
amides
in
46–95%
yield.
More
than
68
products,
including
7
natural
product
derivatives
have
been
synthesized
through
this
method.
Mechanism
study
showed
act
as
Lewis
base
C=C
double
bond
trigger
ring‐opening
reaction.
HRMS
analysis
indicated
formation
key
adduct
cyclopropenone.
importantly,
demonstrated
completely
different
catalytic
activity
catalysts,
latter
one
cannot
catalyse
these
reactions.
A
metal-free,
visible-light-induced
NHC-catalyzed
multiple-component
reaction
involving
aldehydes
and
aryl
thianthrenium
salts
for
the
carboacylation
of
alkenes
is
reported.
In
this
reaction,
NHC-activated
afforded
Breslow
intermediates,
which
reduced
generated
radicals.
The
resulting
radicals
underwent
radical
addition
reactions
to
yield
arylacylation
products,
in
presence
iodoalkane,
participated
halogen
atom
transfer
process
generate
alkyl
facilitate
olefin
alkylacylation.
