Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(12), С. 3121 - 3126
Опубликована: Апрель 1, 2021
Abstract
Herein,
a
copper(II)‐catalyzed
dearomative
cyclization
amination
of
N‐(2‐aminobenzoyl)
indoles
is
presented.
Under
mild
reaction
conditions,
the
proceeds
to
afford
tetracyclic
indolines
by
forming
new
C−N
bond
in
good
yields.
The
5a,6‐dihydroindolo[2,1‐b]quinazolin‐12(5H)‐ones
are
obtained
excellent
yields
(up
99%
yield)
using
trifluoromethanesulfonic
acid
(TfOH)
mediated
N−Ts
cleavage.
compounds
could
be
easily
functionalized
simple
synthetic
methods.
magnified
image
Chemistry - A European Journal,
Год журнала:
2020,
Номер
27(17), С. 5344 - 5378
Опубликована: Окт. 30, 2020
Isoindolinone
structure
is
an
important
privileged
scaffold
found
in
a
large
variety
of
naturally
occurring
as
well
synthetic,
biologically
and
pharmaceutically
active
compounds.
Owing
to
its
crucial
role
number
applications,
the
synthetic
methodologies
for
accessing
this
heterocyclic
skeleton
have
received
significant
attention
during
past
decade.
In
general,
strategies
can
be
divided
into
two
categories:
First,
direct
utilization
phthalimides
or
phthalimidines
starting
materials
synthesis
isoindolinones;
second,
construction
lactam
and/or
aromatic
rings
by
different
catalytic
methods,
including
C-H
activation,
cross-coupling,
carbonylation,
condensation,
addition
formal
cycloaddition
reactions.
Especially
last
mentioned,
transition
metal
catalysts
provides
access
broad
range
substituted
isoindolinones.
Herein,
recent
advances
(2010-2020)
catalyzed
via
formation
new
C-C
bonds
isoindolinones
are
reviewed.
Molecules,
Год журнала:
2020,
Номер
25(21), С. 4906 - 4906
Опубликована: Окт. 23, 2020
Isocyanides
have
long
been
known
as
versatile
chemical
reagents
in
organic
synthesis.
Their
ambivalent
nature
also
allows
them
to
function
a
CO-substitute
palladium-catalyzed
cross
couplings.
Over
the
past
decades,
isocyanides
emerged
practical
and
C1
building
blocks,
whose
inherent
N-substitution
for
rapid
incorporation
of
nitrogeneous
fragments
wide
variety
products.
Recent
developments
palladium
catalyzed
isocyanide
insertion
reactions
significantly
expanded
scope
applicability
these
imidoylative
cross-couplings.
This
review
highlights
advances
made
this
field
over
eight
years.
ACS Catalysis,
Год журнала:
2021,
Номер
11(21), С. 13217 - 13222
Опубликована: Окт. 15, 2021
A
mild
visible-light-induced
Pd-catalyzed
one-pot
three-component
alkyl-carbamoylation
and
cyanation
of
alkenes
was
developed.
This
general
transformation,
which
proceeds
via
the
in
situ
formation
a
reactive
ketenimine
intermediate,
allows
for
rapid
construction
broad
range
valuable
amides
nitriles
from
readily
available
alkenes,
alkyl
iodides,
isocyanides.
An
efficient
synthesis
tetrazole
amidine
this
approach
also
demonstrated.
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.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(15), С. 2436 - 2466
Опубликована: Июнь 12, 2023
Abstract
Elaborated
molecular
architectures
including
complex
carbocycles,
heterocycles,
and
polycyclic
structures
represent
an
important
class
of
organic
compounds
because
they
are
ubiquitous
structural
units
in
a
broad
variety
biologically
pharmacologically
relevant
natural
products,
medicinal
molecules,
functional
materials.
A
major
challenge
modern
synthetic
methodology
is
the
development
strategically
efficient
selective
construction
these
from
readily
available
starting
Transition‐metal‐catalyzed
transformations
involving
Heck
reaction
as
pivotal
step
have
afforded
powerful
approach
for
accessing
sophisticated
skeletons
set
easy‐to
handle
materials,
thus
highlighting
its
potential
significance
streamlining
drug
discovery
process.
Over
past
few
decades,
significant
effort
has
been
devoted
to
derivatives
versatile
routes,
number
direct
strategies
reported.
In
this
review,
latest
advances
transition‐metal‐catalyzed
critical
summarized,
which
could
be
divided
into
six
categories:
1)
Heck/Sonogashira
tandem
reaction;
2)
Heck/Suzuki
3)
Heck/Heck
4)
Heck/Hiyama
5)
Heck/Cacchi
6)
Heck/C−H
bond
functionalization
reaction.
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(35), С. 7544 - 7574
Опубликована: Янв. 1, 2021
This
review
focuses
on
recent
developments
in
the
synthesis
of
pyrrolo[1,2-
a
]indole
derivatives.
The
mechanism,
factors
affecting
yield
and
selectivity
product,
application
to
bioactive
molecules
are
explained.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(42)
Опубликована: Июль 23, 2022
Herein,
we
present
a
direct
and
efficient
synthesis
of
diverse
polysubstituted
fused
tetracyclic
heterocycles
with
good
functional
group
tolerance
from
diarylalkynes
under
different
palladium
catalytic
systems.
In
this
chemistry,
an
unprecedented
intermolecular
nucleopalladation
through
the
highly
selective
sequential
double
insertion
isocyanide
was
achieved
for
first
time.
The
practicality
method
further
demonstrated
by
construction
various
bioactive
molecules
important
structural
motifs,
potential
applications
in
materials
science
biochemistry.
addition,
density
theory
calculations
(DFT)
elucidated
interesting
"Pd
walk"
during
cyclization
process.
Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(10)
Опубликована: Авг. 3, 2022
Abstract
Polycyclic
fused
indoline
derivatives,
specifically
those
bearing
tertiary
or
quaternary
carbon
stereocenters
at
C2
and
C3
positions,
stand
as
an
important
class
of
nitrogen‐containing
heterocyclic
compounds
because
they
are
frequently
occurring
core
structures
in
a
wide
variety
alkaloid
natural
products,
pharmaceutical
molecules,
functional
materials.
Over
the
past
few
decades,
development
new
versatile
synthetic
approaches
for
construction
indolines
has
been
focus
great
deal
research
initiatives.
In
this
review,
recent
advances
dearomative
annulation
N‐
acylindoles
with
diverse
nucleophiles
summarized
since
2012,
which
could
be
divided
into
five
categories:
1)
Dearomative
Heck
reactions
acylindoles;
2)
Visible‐light‐induced
reductive
dearomatization
3)
Lewis
acid‐catalyzed
4)
Asymmetric
5)
by
other
closely
related
reagents.
ACS Catalysis,
Год журнала:
2021,
Номер
12(2), С. 837 - 845
Опубликована: Дек. 29, 2021
A
1,2-difunctionalization
of
an
unactivated
alkene,
imidoyl-carbamoylation,
has
been
developed
through
a
palladium-catalyzed
four-component
cascade
reaction
involving
aryl
iodide,
alkenyl
isocyanide,
CO,
and
amine.
Continuous
migratory
insertion
three
different
functionalities
to
the
Pd(II)
intermediate
generated
from
previous
step
takes
place
in
well-defined
sequence.
Four
chemical
bonds,
including
C–C
bonds
one
C–N
bond,
are
formed
this
process,
leading
convenient
convergent
access
acetamides
substituted
with
five-
seven-membered
cyclic
ketoimines.
In
addition,
extra
bond
is
situ
or
postreaction
cyclization
amido
NH
ketoimine
moiety,
providing
facile
one-pot
pyrrolo-fused
heterocycles.
