Asian Journal of Organic Chemistry,
Год журнала:
2019,
Номер
8(11), С. 2042 - 2045
Опубликована: Окт. 14, 2019
Abstract
An
efficient
and
convenient
silver‐catalyzed
procedure
was
developed
for
the
synthesis
of
various
phosphoryl‐substituted
benzimidazo[2,1‐
a
]isoquinoline‐6(5
H
)‐ones
from
diarylphosphine
oxides
2‐arylbenzoimidazoles.
Moreover,
indolo[2,1‐
]isoquinolin‐6(5
could
also
be
achieved
by
using
this
strategy
under
mild
reaction
conditions
in
presence
AgNO
3
/K
2
S
O
8
.
ACS Catalysis,
Год журнала:
2020,
Номер
10(12), С. 6676 - 6681
Опубликована: Май 29, 2020
Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one
derivatives
are
prevalent
in
many
synthetic
intermediates,
pharmaceuticals,
and
organic
materials.
Herein,
we
develop
a
Mn-catalyzed
electrochemical
radical
cascade
cyclization
reaction
that
uses
electricity
as
the
primary
energy
input
to
promote
reaction,
leading
series
of
benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one
under
exogenous-oxidant-free
conditions.
It
is
worth
noting
this
method
can
not
only
realize
synthesis
but
also
provides
new
strategy
for
generating
alkyl
radicals
from
alkylboronic
acids.
Asian Journal of Organic Chemistry,
Год журнала:
2021,
Номер
10(4), С. 711 - 748
Опубликована: Фев. 11, 2021
Abstract
Photocatalyzed
organic
synthesis
transformation
is
a
remarkable
green
synthetic
strategy
because
of
the
advantages
operational
simplicity,
high
chemoselectivities,
cheap,
and
environmental
benignancy,
along
with
extensive
applications
in
fields
organic,
pharmaceutical
functional
material
chemistry.
Generally,
photoredox
catalysts
or
photosensitizers
are
necessary
for
generation
their
excited
states
to
perform
successive
oxidative
reductive
reactions
through
single
electron
transfer
(SET)
energy
(ET)
process.
Furthermore,
exploration
colored
donor‐acceptor
(EDA)
complex
charge
(CT)
between
an
electron‐rich
electron‐poor
substrate
provides
chance
deliver
intermediate
under
irradiation
light,
resulting
formation
radical
activate
species
induce
various
reactions.
These
were
performed
without
need
any
external
photocatalysts
mild
reaction
conditions.
Herein,
this
review
focuses
on
recent
progress
photoinduced
addition
reactions,
borylations,
radical‐radical
cross‐coupling
degradation
cascade
cyclization
via
EDA
complexes.
We
highlight
these
novel
methodologies
applications,
as
well
mechanisms.
This
will
help
provide
references
medicinal
chemists
who
charmed
by
photochemical
transformations
based
Chemical Communications,
Год журнала:
2019,
Номер
55(19), С. 2861 - 2864
Опубликована: Янв. 1, 2019
A
simple
and
efficient
decarboxylative
radical
addition/cyclization
strategy
was
developed,
by
which
a
wide
range
of
benzimidazo[2,1-a]isoquinoline-6(5H)-ones
were
prepared
in
one-pot
via
reaction
functionalized
2-arylbenzoimidazoles
carboxylic
acids
the
presence
K2S2O8/AgNO3
under
mild
conditions.
Advanced Synthesis & Catalysis,
Год журнала:
2019,
Номер
361(22), С. 5176 - 5181
Опубликована: Сен. 26, 2019
Abstract
A
metal‐free
visible‐light‐induced
cyclization
procedure
was
developed
for
the
rapid
synthesis
of
perfluoroalkyl‐substituted
benzimidazo[2,1‐
a
]isoquinolin‐6(5
H
)‐ones
and
indolo[2,1‐
under
mild
reaction
conditions.
In
this
procedure,
formation
electron‐donor‐acceptor
(EDA)
complex
is
critical
visible‐light
promoted
process
to
avoid
utilization
external
photocatalysts.
magnified
image
Beilstein Journal of Organic Chemistry,
Год журнала:
2023,
Номер
19, С. 1055 - 1145
Опубликована: Июль 28, 2023
Photoredox
catalysis
(PRC)
is
a
cutting-edge
frontier
for
single
electron-transfer
(SET)
reactions,
enabling
the
generation
of
reactive
intermediates
both
oxidative
and
reductive
processes
via
photon
activation
catalyst.
Although
this
represents
significant
step
towards
chemoselective
and,
more
generally,
sustainable
chemistry,
its
efficacy
limited
by
energy
visible
light
photons.
Nowadays,
excellent
alternative
conditions
are
available
to
overcome
these
limitations,
harvesting
two
different
but
correlated
concepts:
use
multi-photon
such
as
consecutive
photoinduced
electron
transfer
(conPET)
combination
photo-
electrochemistry
in
synthetic
photoelectrochemistry
(PEC).
Herein,
we
review
most
recent
contributions
fields
activations
organic
functional
groups.
New
opportunities
chemists
captured,
selective
reactions
employing
super-oxidants
super-reductants
engage
unactivated
chemical
feedstocks,
scalability
up
gram
scales
continuous
flow.
This
provides
comparisons
between
techniques
(multi-photon
photoredox
PEC)
help
reader
fully
understand
their
similarities,
differences
potential
applications
therefore
choose
which
method
appropriate
given
reaction,
scale
purpose
project.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(17)
Опубликована: Фев. 22, 2024
Abstract
To
date,
it
remains
challenging
to
achieve
a
general
and
catalytic
α‐arylation
of
cyclic
1,3‐dicarbonyls,
particularly
ubiquitous
heteroaromatic
ones.
In
most
cases,
the
preparation
their
medically
significant
arylated
derivatives
requires
multistep
synthetic
sequences.
Herein,
we
introduce
new,
convenient
strategy
involving
conversion
1,3‐dicarbonyls
iodonium
ylides
(
CIY
s),
followed
by
rhodium‐catalyzed
with
arylboronic
reagents
via
carbene
coupling.
This
approach
is
mild,
operationally
simple,
base‐free,
biocompatible,
exhibits
broad
substrate
scope
(>100
examples),
especially
respect
various
ortho
‐substituted
or
base‐sensitive
acids.
Importantly,
owing
excellent
compatibility
acids
boronate
esters
(ArBpin,
ArBneop,
ArBF
3
K),
this
method
allows
late‐stage
installation
heterocyclic
1,3‐dicarbonyl
motifs
in
highly
complex
settings.
The
utility
transformation
further
demonstrated
through
significantly
simplifying
synthesis
several
bioactive
molecules
natural
products.
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
362(10), С. 1947 - 1954
Опубликована: Фев. 18, 2020
Abstract
Here,
a
mild
and
general
oxidative
radical
relay
carbocyclization
reaction
with
2‐arylbenzoimidazoles
cyclic
ethers
is
reported.
This
method
provides
an
efficient
access
to
wide
range
of
structurally
diverse
benzimidazo[2,1‐
]isoquinoline‐6(5
H
)‐ones
under
metal‐free
conditions.
The
substrate
scope,
good
functional
group
tolerance,
scale‐up
operation
this
are
expected
promote
its
potential
applications
in
biotechnology
pharmacy.
magnified
image
Organic Chemistry Frontiers,
Год журнала:
2019,
Номер
6(21), С. 3688 - 3692
Опубликована: Янв. 1, 2019
A
rhodium(iii)-catalyzed
C–H
activation/annulation
of
salicylaldehydes
with
sulfoxonium
ylides
has
been
developed
for
the
formation
structurally
diverse
2-substituted
chromones.
Organic & Biomolecular Chemistry,
Год журнала:
2020,
Номер
18(25), С. 4843 - 4847
Опубликована: Янв. 1, 2020
A
simple
and
practical
method
for
the
synthesis
of
phosphoryl-substituted
indolo[2,1-a]isoquinolin-6(5H)-ones
benzimidazo[2,1-a]isoquinolin-6(5H)-ones
through
manganese(iii)-promoted
tandem
phosphinoylation/cyclization
2-arylindoles
or
2-arylbenzimidazoles
with
disubstituted
phosphine
oxides
was
developed.
In
this
transformation,
new
C-P
bond
C-C
were
constructed
simultaneously
under
silver-free
conditions,
exhibiting
a
broad
substrate
scope.
It
noted
that
not
only
diarylphosphine
but
also
dialkyl
arylalkyl-phosphine
compatible
conditions.