Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 21, 2025
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.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(4), P. 790 - 790
Published: Feb. 8, 2024
Monofluoromethyl
(CH2F)
motifs
exhibit
unique
bioactivities
and
are
considered
privileged
units
in
drug
discovery.
The
radical
monofluoromethylative
difunctionalization
of
alkenes
stands
out
as
an
appealing
approach
to
access
CH2F-containing
compounds.
However,
this
strategy
remains
largely
underdeveloped,
particularly
under
metal-free
conditions.
In
study,
we
report
on
visible
light-mediated
three-component
monofluoromethylation/acylation
styrene
derivatives
employing
NHC
organic
photocatalyst
dual
catalysis.
A
diverse
array
α-aryl-β-monofluoromethyl
ketones
was
successfully
synthesized
with
excellent
functional
group
tolerance
selectivity.
mild
CH2F
generation
from
NaSO2CFH2
holds
potential
for
further
applications
fluoroalkyl
chemistry.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 14, 2024
Cyclobutanes
are
prominent
structural
components
in
natural
products
and
drug
molecules.
With
the
advent
of
strain-release-driven
synthesis,
ring-opening
reactions
bicyclo[1.1.0]butanes
(BCBs)
provide
an
attractive
pathway
to
construct
these
three-dimensional
structures.
However,
stereoselective
difunctionalization
central
C-C
σ-bonds
remains
challenging.
Reported
herein
is
a
covalent-based
organocatalytic
strategy
that
exploits
radical
NHC
catalysis
achieve
diastereoselective
acylfluoroalkylation
BCBs
under
mild
conditions.
The
Breslow
enolate
acts
as
single
electron
donor
provides
NHC-bound
ketyl
with
appropriate
steric
hindrance,
which
effectively
distinguishes
between
two
faces
transient
cyclobutyl
radicals.
This
operationally
simple
method
tolerates
various
fluoroalkyl
reagents
common
functional
groups,
providing
straightforward
access
polysubstituted
cyclobutanes
(75
examples,
up
>19
:
1
d.r.).
combined
experimental
theoretical
investigations
this
system
confirm
formation
NHC-derived
understanding
how
radical-radical
coupling
occurs.
Synlett,
Journal Year:
2023,
Volume and Issue:
35(04), P. 445 - 450
Published: Aug. 1, 2023
Abstract
Cooperative
NHC
and
photoredox
catalysis
has
gained
significant
attention
as
an
emerging
research
field
in
recent
years.
Herein,
we
report
a
cyclizing
aminoacylation
of
alkenes,
which
is
enabled
through
the
combination
these
two
catalytic
modes.
The
key
step
radical/radical
cross-coupling
between
persistent
ketyl
radical
transient
benzylic
or
aliphatic
C-radical,
generated
cyclization
oxidatively
formed
amidyl
radical.
Several
carbamates,
amides
sulfonamides
containing
alkene
moiety
different
acyl
fluorides
can
be
used
substrates.
resulting
products
are
obtained
moderate
to
good
yields.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(48), P. 8677 - 8682
Published: Nov. 23, 2023
Pyrroloindoline
is
a
privileged
heterocyclic
motif
that
widely
present
in
many
natural
products
and
pharmaceutical
compounds.
Herein,
we
report
an
amidyl
radical-mediated
dearomatization
for
synthesizing
series
of
pyrroloindolines
via
N-heterocyclic
carbene
catalysis.
In
this
organocatalytic
process,
the
Breslow
enolate
served
as
both
single
electron
donor
acyl
radical
equivalent
to
assemble
C3a-acyl
with
broad
substrate
scope.
Sequential
reduction
indole
derivatives
provided
analogues
(±)-desoxyeseroline,
which
exhibited
potential
anticancer
activity.
Catalysis Science & Technology,
Journal Year:
2024,
Volume and Issue:
14(18), P. 5143 - 5160
Published: Jan. 1, 2024
This
review
article
summarizes
the
visible
light
mediated
synthesis
of
allenes
from
substrates
like
1,3-enynes,
propargylic
carbonates,
homopropargylic
alcohols,
oxalates,
alkynyl
diazo
compounds,
and
terminal
aziridines.
