Organic Letters,
Год журнала:
2024,
Номер
26(6), С. 1265 - 1270
Опубликована: Фев. 6, 2024
The
hydroarylation
of
alkenes
has
emerged
as
a
powerful
strategy
for
arene
functionalization.
However,
aryl
chlorides
remain
large
challenge
in
this
type
reaction
due
to
the
chemical
inertness
C(sp2)–Cl
bond
and
high
negative
reduction
potential.
Herein,
we
report
an
anti-Markovnikov
radical
with
via
visible-light
photoredox
catalysis.
key
reactive
radicals
can
be
efficiently
achieved
from
by
consecutive
photoinduced
electron
transfer.
This
transition-metal-free
protocol
features
mild
conditions,
wide
substrate
scope,
functional
group
tolerance,
producing
diverse
range
linear
alkylarenes
moderate
good
yields.
is
proposed
proceed
through
radical-polar
crossover
pathway.
Organic Letters,
Год журнала:
2021,
Номер
23(11), С. 4353 - 4357
Опубликована: Май 18, 2021
Radical
hydroboration
reactions
have
only
recently
been
reported
and
are
still
rare.
Here
we
describe
a
photoredox
radical
of
α,β-unsaturated
esters,
amides,
ketones,
nitriles
with
NHC-boranes
that
uses
an
organocatalyst
visible
light.
The
conditions
mild,
the
substrate
scope
is
broad,
α/β
regioselectivity
high.
reaction
requires
organocatalyst;
there
no
costly
metal,
other
additives
(base,
cocatalyst,
initiator).
Angewandte Chemie International Edition,
Год журнала:
2021,
Номер
60(48), С. 25235 - 25240
Опубликована: Сен. 24, 2021
We
report
an
approach
for
the
intramolecular
C(sp2
)-H
amidation
of
N-acyloxyamides
under
photoredox
conditions
to
produce
δ-benzolactams
with
aryl-alkyl
σ-bond
relocation.
Computational
studies
on
designed
reductive
single
electron
transfer
strategy
led
us
identify
N-[3,5-bis(trifluoromethyl)benzoyl]
group
as
most
effective
amidyl
radical
precursor.
Upon
formation
azaspirocyclic
intermediate
by
selective
ipso-addition
outcompeting
ortho-attack,
radical-polar
crossover
was
then
rationalized
lead
rearomative
ring-expansion
preferential
C-C
bond
migration.
Organic Letters,
Год журнала:
2021,
Номер
23(16), С. 6257 - 6261
Опубликована: Июль 29, 2021
The
intermolecular
dearomative
cycloaddition
of
acidified
bicyclic
azaarenes
with
olefins
was
recently
reported.
We
report
here
the
crucial
role
acid
in
photocycloaddition
quinolines
to
olefins.
Experimental
and
theoretical
results
show
that
key
protonation
is
not
promote
energy
transfer
but
enhance
reactivity
triplet
state
toward
Organic Letters,
Год журнала:
2022,
Номер
24(5), С. 1213 - 1218
Опубликована: Фев. 2, 2022
A
mild
visible-light-driven
palladium-catalyzed
radical
tandem
dearomatization
of
indoles
with
unactivated
alkenes
is
described
moderate
to
good
yields
and
excellent
diastereoselectivities.
Under
visible-light
irradiation,
the
photoexcited
state
palladium
complex
was
formed,
which
could
transfer
a
single
electron
N-(2-bromobenzoyl)indoles,
leading
hybrid
chemistry.
This
provides
efficient
atom-economical
access
diverse
2,3-disubstituted
indoline
derivatives.
Organic Letters,
Год журнала:
2024,
Номер
26(6), С. 1265 - 1270
Опубликована: Фев. 6, 2024
The
hydroarylation
of
alkenes
has
emerged
as
a
powerful
strategy
for
arene
functionalization.
However,
aryl
chlorides
remain
large
challenge
in
this
type
reaction
due
to
the
chemical
inertness
C(sp2)–Cl
bond
and
high
negative
reduction
potential.
Herein,
we
report
an
anti-Markovnikov
radical
with
via
visible-light
photoredox
catalysis.
key
reactive
radicals
can
be
efficiently
achieved
from
by
consecutive
photoinduced
electron
transfer.
This
transition-metal-free
protocol
features
mild
conditions,
wide
substrate
scope,
functional
group
tolerance,
producing
diverse
range
linear
alkylarenes
moderate
good
yields.
is
proposed
proceed
through
radical-polar
crossover
pathway.
