Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(60)
Опубликована: Июль 28, 2023
The
recent
disclosure
of
the
ability
aromatic
isocyanides
to
harvest
visible
light
and
act
as
single
electron
acceptors
when
reacting
with
tertiary
amines
has
triggered
a
renewed
interest
in
their
application
development
green
photoredox
catalytic
methodologies.
Accordingly,
present
work
explores
promote
generation
both
alkyl
acyl
radicals
starting
from
radical
precursors
such
Hantzsch
esters,
potassium
alkyltrifluoroborates,
α-oxoacids.
Mechanistic
studies
involving
UV-visible
absorption
fluorescence
experiments,
electrochemical
measurements
ground-state
redox
potentials
along
computational
calculations
ground-
excited-state
set
nine
different
provide
key
insights
rationale
design
new
isocyanide-based
organic
catalysts.
Importantly,
potential
investigated
chemistry
is
demonstrated
by
direct
easy
access
deuterium
labeled
compounds.
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(49), С. 20863 - 20872
Опубликована: Дек. 1, 2021
Electrochemical
synthesis
has
been
rapidly
developed
over
the
past
few
years,
while
a
vast
majority
of
reactions
proceed
through
radical
pathway.
Understanding
properties
intermediates
is
crucial
in
mechanistic
study
electrochemical
transformations
and
will
be
beneficial
for
developing
new
reactions.
Nevertheless,
it
rather
difficult
to
determine
"live"
due
their
high
reactivity.
In
this
work,
formation
structure
sulfonamide
N-centered
radicals
have
researched
directly
by
using
time-resolved
electron
paramagnetic
resonance
(EPR)
technique
under
conditions.
Supported
EPR
results,
reactivity
as
mediator
hydrogen
atom
transfer
(HAT)
approach
discussed.
Subsequently,
these
results
successfully
utilized
discovery
an
unactivated
C(sp3)–H
arylation
reaction.
The
kinetic
experiments
revealed
rate-determined
step
anodic
oxidation
sulfonamides.
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(22), С. 12293 - 12304
Опубликована: Май 19, 2023
Recent
mechanistic
studies
of
dual
photoredox/Ni-catalyzed,
light-driven
cross-coupling
reactions
have
found
that
the
photocatalyst
(PC)
operates
through
either
reductive
quenching
or
energy
transfer
cycles.
To
date,
reports
invoking
oxidative
cycles
are
comparatively
rare
and
direct
observation
such
a
event
has
not
been
reported.
However,
when
PCs
with
highly
reducing
excited
states
used
(e.g.,
Ir(ppy)
Chemical Communications,
Год журнала:
2024,
Номер
60(50), С. 6340 - 6361
Опубликована: Янв. 1, 2024
In
this
review,
the
state-of-the-art
advances
in
radical-involved
C(sp
3
)–N
bond
formation
via
metallaphotoredox
catalysis
have
been
highlighted,
which
are
organized
according
to
different
catalytic
modes,
reaction
types,
and
substrate
classes.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(5), С. 3251 - 3258
Опубликована: Фев. 15, 2024
Aziridines
are
important
structural
motifs
and
intermediates,
several
synthetic
strategies
for
the
direct
aziridination
of
alkenes
have
been
introduced.
However,
many
these
require
an
excess
activated
alkene,
suffer
from
competing
side-reactions,
limited
functional
group
tolerance,
or
involve
precious
transition
metal-based
catalysts.
Herein,
we
demonstrate
by
combining
sulfonyl
azides
as
a
triplet
nitrene
source
with
catalytic
amount
organic
dye
functioning
photosensitizer.
We
show
how
nature
azide,
in
combination
triplet-excited
state
energy
photosensitizer,
affects
yield
provide
mechanistic
rationale
to
account
observed
dependence
reaction
on
azide
reagents.
The
optimized
conditions
enable
structurally
diverse
complex
alkenes,
carrying
various
groups,
alkene
limiting
reagent.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(9), С. 5556 - 5567
Опубликована: Апрель 20, 2022
An
efficient
Ru
doped
hydrotalcite
catalyzed
N-alkylation
of
benzamides
and
sulfonamides
with
alcohols
via
borrowing
hydrogen
catalysis
is
illustrated.
Various
primary
alcohols,
including
benzyl,
heteroaryl,
aliphatic
were
alkylated
in
good
to
excellent
yields.
To
shed
light
on
the
mechanistic
details,
several
control
studies
deuterium
labeling
experiments
performed.
Mechanistic
underpin
that
reaction
going
a
pathway
rather
than
an
SN1
type
mechanism.
The
can
be
easily
scaled
up
without
any
detrimental
effect
yield.
catalyst
also
capable
synthesizing
quinazolinone
directly
from
2-aminobenzamide
alcohols.
Successful
recyclability
high
reactivity
highlight
practical
applicability
catalyst.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(15), С. 11161 - 11172
Опубликована: Июль 25, 2023
Sulfones
are
widely
found
in
natural
products
and
drug
molecules.
Here,
we
disclose
a
strategy
for
direct
synthesis
of
sulfone
compounds
with
diverse
structures
by
visible-light-catalyzed
radical-radical
cross-coupling
sulfonyl
chlorides
trifluoroborate
salts.
Allyl,
benzyl,
vinyl,
aryl
trifluoroborates
can
be
successfully
cross-coupled
(hetero)aryl
alkyl
chlorides,
respectively.
This
features
redox
neutrality,
good
substrate
generality,
simple
operation,
benign
reaction
conditions.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(7), С. 1559 - 1564
Опубликована: Фев. 14, 2024
Abstract
A
photoredox/copper
co‐catalyzed
ring‐opening
cross‐coupling
of
aryl
azides
with
cyclopropanols
has
been
developed
fac
‐Ir(ppy)
3
as
the
photocatalyst.
The
reaction
involves
intermediacy
anilino
radical
generated
through
reduction
azido
group
by
*
and
[Cu
II
]‐enabled
oxidative
cyclopropanol.
An
array
β‐aminoketone
compounds
were
synthesized
under
redox‐neutral
conditions
using
this
method.
