Recent advances in C(sp3)–N bond formation via metallaphoto-redox catalysis
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.
Язык: Английский
Photocatalysis Meets Copper Catalysis: A New Opportunity for Asymmetric Multicomponent Radical Cross-Coupling Reactions
Accounts of Chemical Research,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 13, 2024
ConspectusIn
recent
years,
radical-mediated
cross-coupling
reactions
have
emerged
as
a
compelling
strategy
for
achieving
rich
diversity
in
molecular
topologies
under
benign
conditions.
However,
the
inherent
high
reactivity
of
radicals
presents
considerable
challenges
controlling
reaction
pathways
and
selectivity,
which
often
results
limited
range
substrates
constrained
profile.
Given
capacity
visible-light
photoredox
catalysis
to
generate
wide
variety
reactive
radical
ions
controlled
manner
propensity
copper
complexes
toward
species,
we
envisaged
that
synergy
between
chiral
catalysts
photoactive
would
pave
way
developing
innovative
strategies.
This
integration
is
poised
unlock
broad
spectrum
enantioselective
multicomponent
reactions.In
this
Account,
describe
our
insights
efforts
realm
reactions.
These
advancements
been
achieved
through
application
dual
photoredox/copper
or
bifunctional
visible
light
irradiation.
Our
work
systematically
divided
into
two
sections
based
on
activation
modes.
The
first
section
focuses
photoinduced
copper-catalyzed
C-C
C-O
bond
formation
addition/nucleophilic
trap
sequence.
discussion
particularly
concentrated
asymmetric
carbocyanation
carboarylation
vinylarenes,
1,3-enynes,
1,3-dienes.
findings
underscore
irradiation
with
can
adeptly
modulate
pace
generation,
thus
orchestrating
consecutive
stages
ensuring
attainment
both
chemo-
stereoselectivity.
In
domain
formation,
leveraging
carboxylic
acids
nucleophilic
oxygen
source,
introduce
suite
esterification
benzylic,
allylic,
propargylic
radicals.
are
derived
from
precursors,
showcasing
versatility
approach.
following
highlights
discovery
field
catalysis,
enables
three-component
transformations
via
direct
aromatic
alkenes.
methodology
begins
generation
formal
distonic
anions
photocatalytic
single-electron
reduction
alkenes,
thus,
enabling
orthogonal
reactivity.
Employing
H
Язык: Английский
Cooperative Phosphine-Photoredox Catalysis Enables N–H Activation of Azoles for Intermolecular Olefin Hydroamination
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(29), С. 20349 - 20356
Опубликована: Июль 10, 2024
Catalytic
intermolecular
olefin
hydroamination
is
an
enabling
synthetic
strategy
that
offers
direct
and
atom-economical
access
to
a
variety
of
nitrogen-containing
compounds
from
abundant
feedstocks.
However,
despite
numerous
advances
in
catalyst
design
reaction
development,
N-H
azoles
with
unactivated
olefins
remains
unsolved
problem
synthesis.
We
report
dual
phosphine
photoredox
catalytic
protocol
for
the
structurally
diverse
medicinally
relevant
olefins.
Hydroamination
proceeds
high
anti-Markovnikov
regioselectivity
Язык: Английский
Copper‐Catalyzed Aromatization‐Driven Ring‐Opening Amination and Oxygenation of Spiro Dihydroquinazolinones
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(58)
Опубликована: Авг. 8, 2024
Abstract
Mild
and
inexpensive
copper‐catalyzed
aromatization‐driven
ring‐opening
amination
oxygenation
of
spiro
dihydroquinazolinones
are
presented,
respectively.
These
protocols
provide
facile
atom‐economical
access
to
the
aminated
carbonyl‐containing
quinazolin‐4(3
H
)‐ones
in
good
yields
with
functional
group
compatibility,
which
difficult
obtain
by
conventional
methods.
Remarkably,
a
telescoped
procedure
involving
condensation
ring‐opening/functionalization
for
simple
cycloalkanone
was
found
be
accessible.
Mechanistic
studies
suggest
radical
pathway
this
transformation.
Язык: Английский
Visible light-driven excited-state copper-BINAP catalysis for accessing diverse chemical reactions
Chem Catalysis,
Год журнала:
2024,
Номер
4(11), С. 101184 - 101184
Опубликована: Ноя. 1, 2024
Язык: Английский
Cooperative Phosphine-Photoredox Catalysis Enables N–H Activation of Azoles for Intermolecular Olefin Hydroamination
Опубликована: Апрель 30, 2024
Catalytic
intermolecular
olefin
hydroamination
is
an
enabling
synthetic
strategy
that
offers
direct
and
atom-economical
access
to
a
variety
of
nitrogen-containing
compounds
from
abundant
feedstocks.
However,
despite
numerous
advances
in
catalyst
design
reaction
development,
N–H
azoles
with
unactivated
olefins
remains
unsolved
problem
synthesis.
We
report
dual
phosphine
photoredox
catalytic
protocol
for
the
structurally
diverse
medicinally
relevant
olefins.
Hydroamination
proceeds
high
anti-Markovnikov
regioselectivity
N-site
selectivity.
The
mild
conditions
functional
group
tolerance
permit
rapid
construction
molecular
complexity
late-stage
functionalization
bioactive
compounds.
bond
activation
proposed
proceed
via
polar
addition
heterocycle
radical
cation,
followed
by
P–N
α-scission
phosphoranyl
intermediate.
Reac-tivity
selectivity
are
classified
BDFE
nitrogen-centered
(NCR)
spin
density,
respectively,
which
can
serve
as
useful
predictive
aid
extending
unseen
azoles.
Язык: Английский
Photoinduced Copper‐Catalyzed Three‐Component Radical Carboamination of Styrene Derivatives
ChemCatChem,
Год журнала:
2024,
Номер
16(23)
Опубликована: Авг. 28, 2024
Abstract
The
catalytic
three‐component
radical
carboamination
of
alkenes
has
recently
emerged
as
an
alternative
and
robust
platform
for
the
rapid
construction
diverse
valuable
amines.
Despite
great
advances
in
this
field,
new
methods
that
enable
highly
selective
access
to
chemical
space
surrounding
amine
functional
groups
are
still
high
demand.
Herein,
we
report
a
generally
applicable
visible
light‐induced
copper‐catalyzed
cyanoalkylamination
reaction
alkenes,
oxime
carbonates,
benzoyloxycarbamates.
This
protocol
demonstrates
chemo‐selectivity,
broad
substrate
scope,
good
group
tolerance,
providing
variety
cyanoalkylated
aliphatic
amines
with
yields.
Язык: Английский