Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(12)
Published: Jan. 12, 2023
Abstract
Fluoroarenes
are
abundant
and
readily
available
feedstocks.
However,
due
to
the
high
reduction
potentials
of
mono‐fluoroarenes,
their
photoreduction
remains
a
continuing
challenge,
motivating
development
efficient
activation
modes
address
this
issue.
This
report
presents
blue
light‐induced
N‐heterocyclic
carbene
(NHC)‐catalyzed
single
electron
mono‐fluoroarenes
for
biaryl
cross‐couplings.
We
discovered
that
under
light
irradiation,
NHC/
t
BuOK
combination
could
construct
powerful
photoactive
architectures
promote
transfer
C
aryl
−F
bond
via
forming
highly
reducing
NHC
radical
anion.
Notably,
strategy
was
also
successful
reduce
−O,
−N,
−S
bonds
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(9), P. 1845 - 1850
Published: Feb. 26, 2024
The
difunctionalization
of
alkenes
using
aryl
thianthrenium
salts
as
the
sources
has
been
reported
sporadically.
However,
four-component
on
basis
not
thus
far
and
still
remains
a
challenge.
Herein,
visible
light/copper
catalysis-enabled
reaction
salts,
DABCO·(SO
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(31)
Published: March 28, 2024
Abstract
Photoinduced
aryl
radical
generation
is
a
powerful
strategy
in
organic
synthesis
that
facilitates
the
formation
of
diverse
carbon‐carbon
and
carbon‐heteroatom
bonds.
The
synthetic
applications
photoinduced
complex
compounds,
including
natural
products,
physiologically
significant
molecules,
functional
materials,
have
received
immense
attention.
An
overview
current
developments
production
methods
their
uses
given
this
article.
A
generalized
idea
how
to
choose
reagents
approach
for
radicals
described,
along
with
techniques
associated
mechanistic
insights.
Overall,
article
offers
critical
assessment
results
as
well
selection
reaction
parameters
specific
context
cascades,
cross‐coupling
reactions,
functionalization,
selective
C−H
functionalization
substrates.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(25), P. 4598 - 4602
Published: June 16, 2022
N-Heterocyclic
nitrenium
(NHN)
salts,
the
analogues
of
N-heterocyclic
carbenes,
have
attracted
considerable
interest.
However,
relatively
little
is
known
about
their
catalytic
ability
beyond
Lewis
acid
catalysis.
Herein,
we
describe
that
NHNs
can
serve
as
electron
acceptors
for
charge
transfer
complex
photoactivations.
We
showcase
that,
under
blue
light
irradiation,
NHN
salts
could
catalyze
generation
aryl
radicals
from
halides.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(5), P. 3084 - 3091
Published: Feb. 9, 2024
Herein,
we
reported
a
general
strategy
for
the
synthesis
of
sulfur-containing
primary
alcohol
derivatives
by
base-promoted
ring-opening
hydroxylation
cyclic
sulfonium
salts.
A
variety
salts
were
successfully
transformed
into
desired
hydroxylated
products
in
moderate
to
excellent
yields
with
good
functional
group
tolerance.
Moreover,
one-pot
synthesis,
scale-up
reaction,
and
late-stage
functionalization
complex
molecules
demonstrated
practicability
this
synthetic
protocol
field
chemistry.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(31), P. 6652 - 6657
Published: July 26, 2024
We
report
a
visible-light-promoted
cyclization/sulfonylation
cascade
of
N-heterocycles
with
thianthrenium
salts
using
DABSO
as
the
SO2
surrogate.
This
method
features
excellent
functional
group
tolerance,
wide
substrate
scope,
and
late-stage
elaboration
bioactive
relevant
molecules.
Mechanistic
investigations
reveal
that
photoactive
electron
donor–acceptor
(EDA)
complexes
between
DABCO
are
capable
generation
aryl
radicals,
which
induce
following
insertion
by
attacking
DABSO,
thus
triggering
key
radical
cyclization
step.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(17), P. 3541 - 3546
Published: April 24, 2024
Rapid
and
efficient
construction
of
multifunctionalized
skeletons
through
a
one-pot
multicompound
domino
reaction
has
been
recognized
as
simple
practical
strategy.
Herein,
visible-light-enabled
three-component
isothiocyanates,
isocyanides,
thianthrenium
salt-functionalized
arenes
is
presented,
which
affords
facile
approach
to
sulfur-containing
trisubstituted
imidazoles
in
good
yields
with
broad
substrate
scope
excellent
functional
group
tolerance.
The
byproduct
thianthrene
recovered
quantity,
thereby
ultimately
reducing
the
production
chemical
waste.
developed
methodology
potential
value
for
discovery
development
thioimidazole-based
drugs.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(19), P. 13296 - 13305
Published: May 2, 2024
The
activation
of
esters
by
strong
Lewis
acids
via
the
formation
covalent
adducts
is
a
classic
strategy
to
give
reactivity;
however,
this
approach
frequently
incurs
limited
turnover
due
low
efficiency
in
dissociation
catalyst
from
stable
catalyst-product
complex.
While
use
some
weak
interaction
catalysts
that
can
easily
dissociate
any
bonding
complexes
reaction
system
would
solve
problem,
poor
catalytic
activity
ester
be
provided
these
noncovalent
forces
turn
sets
up
formidable
challenge.
Herein,
we
describe
and
transformation
interactions,
which
provides
promising
platform
reconcile
problems.
Several
tailored
chalcogen-bonding
were
developed
for
esters,
enabling
achieving
several
inherently
reactive
Diels–Alder
reactions
as
well
ring-opening
polymerization
lactones
through
chalcogen
interactions.
This
supramolecular
catalysis
particularly
highlighted
its
capability
promote
uncommon
involving
using
dienes
bearing
electron-withdrawing
groups
coupled
α,β-unsaturated
dienophiles
substrate
incorporating
competitive
basic
sites,
typical
showed
efficiency,
while
representative
hydrogen
halogen
inactive.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(37), P. 7949 - 7955
Published: Sept. 11, 2024
A
novel
electron
donor-acceptor
(EDA)
complex/copper
catalysis
model
has
been
proposed
for
the
construction
of
2,3-diarylpropionitriles
under
visible
light
conditions.
The
developed
protocol
proceeds
via
intermolecular
charge
transfer
between
photoactive
EDA
complex
dibutamine
(DBA),
aryl
thianthrenium
salts,
and
trimethylsilyl
cyanide
(TMSCN),
followed
by
a
copper
catalytic
cycle.
UV-vis
absorption
measurements
confirm
participation
complexes
as
reactive
intermediates.
This
three-component
process
smoothly
in
presence
pharmaceutically
relevant
core
structures
sensitive
functional
groups,
which
offers
possibility
precise
editing
drug
molecules
with
important
scaffolds.
Chalconium
and
halonium
salts
catalyze
Schiff
condensation.
Kinetic
data
DFT
calculations
show
that
the
catalytic
activity
correlates
with
maximum
electrostatic
potential
on
σ-holes,
whereas
other
factors
are
less
significant.