Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(21), С. 3630 - 3650
Опубликована: Окт. 3, 2022
Abstract
Electron‐withdrawing
groups
(EWG)
have
emerged
as
a
powerful
tool
for
the
activation
of
various
arenes
to
promote
nucleophilic
dearomative
additions
construction
complicated
chiral
cyclic
structures
under
asymmetric
catalytic
systems.
Nitro‐indoles,
nitro‐benzofurans/benzothiophenes,
and
related
nitro‐heteroarenes
are
widely
applied
in
reaction
with
nucleophiles
construct
enantioenriched
polycyclic
skeletons
via
dearomatization
process.
Meanwhile,
electron‐deficient
azo‐group
nitroso‐group
an
alternative
arenes,
which
enable
formal
aromatic
arylations
electrophilic
aromatics
novel
biaryl
atropisomers.
Besides,
azo‐naphthanenes
served
dipolar
surrogates
dipolarophiles
proceed
cycloadditions
skeletons.
The
EWG‐tethered
arene
has
proven
be
versatile
protocol
structurally
diversified
backbones.
This
review
summarizes
latest
progress
involved
transformations
organo‐
or
transition
metal
catalysis.
magnified
image
Organic Chemistry Frontiers,
Год журнала:
2020,
Номер
7(23), С. 3967 - 3998
Опубликована: Янв. 1, 2020
This
review
summarizes
the
progresses
in
organocatalytic
asymmetric
dearomatization
reactions
of
indole
derivatives
and
their
applications
total
synthesis
natural
products,
gives
some
insights
into
challenging
issues
this
research
field.
Chinese Journal of Chemistry,
Год журнала:
2019,
Номер
38(3), С. 287 - 294
Опубликована: Дек. 12, 2019
When
“dark”
is
bright
:
the
scarcely
explored
electrophilic
profile
of
indolyl
core
(
dark‐side
)
continues
to
inspire
developments
in
organic
synthesis
by
means
new
catalytic
methodologies.
Recent
advancements
field
enabled
molecular
diversity
and
complexity
be
effectively
realized
within
heterocyclic
chemistry.
Chemical Communications,
Год журнала:
2020,
Номер
57(1), С. 27 - 44
Опубликована: Ноя. 25, 2020
3-Nitroindoles
behave
as
electron-poor
aromatic
compounds
and
react
toward
a
number
electron-rich
species.
This
feature
article
presents
an
overview
of
this
reactivity,
mainly
in
(formal)
dearomatizing
cycloaddition
reactions.
Organic Letters,
Год журнала:
2021,
Номер
23(21), С. 8600 - 8605
Опубликована: Окт. 21, 2021
An
enantioselective
dearomative
1,3-dipolar
cycloaddition
of
2-nitrobenzothiophenes
and
isatin-derived
azomethine
ylides
with
a
bifunctional
hydrogen-bonding
thiourea
catalyst
was
established,
giving
polyheterocyclic
compounds
in
excellent
results
(up
to
99%
yield,
>20:1
dr
for
all
cases
up
ee).
The
enantioselectivity
could
be
reversed
by
the
squaramide
containing
same
chiral
source
as
catalyst.
DFT
calculations
revealed
origin
observed
stereochemistry
reversal
enantioselectivity.
Organic Letters,
Год журнала:
2022,
Номер
24(3), С. 826 - 831
Опубликована: Янв. 14, 2022
We
disclose
a
Ag-catalyzed
asymmetric
interrupted
Barton–Zard
reaction
of
α-aryl-substituted
isocyanoacetates
with
2-
and
3-nitroindoles,
which
enables
the
dearomatization
nitroindoles
hence
offers
rapid
access
to
an
array
optically
active
tetrahydropyrrolo[3,4-b]indole
derivatives
bearing
three
contiguous
stereogenic
centers,
including
two
tetrasubstituted
chiral
carbon
atoms
pretty
outcomes
(up
99%
yield,
91:9
dr,
96%
ee).
The
synthetic
potential
protocol
was
showcased
by
gram-scale
versatile
transformations
product.
Asian Journal of Organic Chemistry,
Год журнала:
2021,
Номер
10(5), С. 932 - 948
Опубликована: Март 10, 2021
Abstract
This
review
article
discusses
about
the
recent
developments
in
area
of
strategies
for
dearomatization
benzofurans
and
benzothiophenes
(2010–2020).
The
readers
can
understand
current
state
art
this
intriguingly
important
organic
synthesis
generation
diversely
functionalized
molecules,
polycyclic
systems
from
highly
abundant
benzothiophenes.
We
hope
that
would
help
synthetic
community
design
development
new
as
well
further
growth
novel
rapidly
growing
research.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(9), С. 6025 - 6037
Опубликована: Апрель 18, 2022
A
dearomatization
process
of
3-nitroindoles
enabled
using
palladium-catalyzed
decarboxylative
[4
+
2]
cycloaddition
either
2-alkylidenetrimethylene
carbonates
or
2-(hydroxymethyl)-3-arylallyl
has
been
developed,
affording
a
wide
range
indoline-fused
tetrahydropyrans
in
good
yields
with
excellent
diastereoselectivities.
This
reaction
features
substrate
scope
and
mild
conditions
represents
the
first
example
application
π-allyl
palladium
1,4-[O,C]-dipole
species
for
dearomative
electron-deficient
heteroarenes.
Organic Letters,
Год журнала:
2020,
Номер
22(24), С. 9699 - 9705
Опубликована: Дек. 9, 2020
Dearomatization
of
indole
derivatives
offers
a
straightforward
approach
to
access
diverse
indolines.
To
date,
the
corresponding
dearomative
transformations
involving
electron-deficient
indoles
are
limited.
Herein,
we
report
one-electron
strategy
for
dearomatization
via
photoredox-catalyzed
hydroalkylation
employing
commercially
available
glycine
as
hydrofunctionalization
reagents.
Followed
by
DBU-mediated
lactamization,
structurally
appealing
lactam-fused
indolines
obtained
in
good
excellent
yields
with
exclusive
selectivity.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(22), С. 6330 - 6336
Опубликована: Янв. 1, 2021
An
organocatalytic
asymmetric
dearomative
[4
+
2]
annulation
of
2-nitrobenzofurans
and
5
H
-thiazol-4-ones
is
developed
for
the
construction
dihydrobenzofuran-bridged
polycyclic
skeletons
with
good
results.
Chemistry - A European Journal,
Год журнала:
2019,
Номер
25(60), С. 13688 - 13693
Опубликована: Сен. 11, 2019
3-Nitroindoles
are
easily
reacted
with
highly
substituted
γ-allenoates
in
the
presence
of
a
commercially
available
phosphine
catalyst.
For
instance,
allenoates
derived
from
biomolecules
such
as
amino
and
deoxycholic
acids
combined
for
first
time
3-nitroindole.
The
corresponding
dearomatized
(3+2)
tricyclic
cycloadducts
obtained
α-regioisomers
exclusively.
DFT
computations
shed
light
on
this
multi-step
reaction
mechanism
selectivities
observed
sequence.
