Chemistry - A European Journal,
Год журнала:
2023,
Номер
30(7)
Опубликована: Ноя. 6, 2023
Reaching
the
formidable
C-H
corners
has
been
one
of
top
priorities
organic
chemists
in
recent
past.
This
prompted
us
to
disclose
herein
a
vicinal
annulation
2-iodo
benzoates,
indoles,
and
carbazoles
with
N-embedded
1,6-enynes
through
7-/8-membered
palladacycles.
The
relay
does
not
require
assistance
any
directing
group,
leading
multicyclic
scaffolds,
which
are
readily
diversified
an
array
adducts
(with
new
functional
tethers
and/or
three
contiguous
stereocenters),
we
showcase
rare
benzylic
mono-oxygenation.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(11), С. 2710 - 2771
Опубликована: Янв. 1, 2021
This
review
presents
a
critical
and
authoritative
analysis
of
several
exciting
benzannulation
approaches
developed
in
the
past
decade
for
construction
carbazoles,
indolocarbazoles,
benzocarbazoles,
carbolines.
We
report
the
Pd-catalyzed
and
Ag-mediated
temperature-dependent
divergent
synthesis
of
tetrahydropyrano[4,3-c]pyran
hexahydrofuro[2,3-b]pyran
derivatives
from
a
single
substrate,
alkynols.
The
reaction
involves
homocoupling
alkynols
to
form
two
C–O
bonds
one
C–C
bond,
resulting
in
cores
at
high
temperature
(110
°C).
Exposing
tetrahydropyrano[4,3-c]pyrans
200
W
tungsten
filament
bulb
yields
tetrahydrofuro[2,3-b]pyrans.
At
lower
temperatures
(30–60
°C),
produce
hexahydrofuro[2,3-b]pyrans.
density
functional
theory
study
explains
selectivity.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(24), С. 4837 - 4845
Опубликована: Янв. 1, 2022
Transition-metal-catalyzed
directed
C-H
alkenylation
with
maleimides
has
attracted
much
attention
in
recent
years,
as
maleimide
core
moieties
are
present
various
natural
products
and
pharmaceuticals.
In
addition,
these
derivatives
can
be
readily
modified
into
biologically
important
compounds
including
succinimides,
pyrrolidines
γ-lactams.
The
efficient
chelation-assisted
inert
bond
activation
strategy
provides
straightforward
access
to
a
wide
array
of
structurally
diverse
molecules
containing
units.
This
review
describes
the
major
progress
mechanistic
investigations
on
Heck-type
reaction/cyclization
organic
until
early
2022.
Organic Letters,
Год журнала:
2023,
Номер
25(15), С. 2594 - 2599
Опубликована: Апрель 10, 2023
We
herein
demonstrate
the
acylsilane-directed
Rh-catalyzed
arene
C–H
bond
alkylation
with
maleimides.
The
resulting
derivatives
were
utilized
in
visible-light-induced
intramolecular
siloxycarbene-amide
cyclization
for
synthesis
of
new
tricyclic
γ-lactams.
In
parallel,
we
also
harnessed
same
acylsilane
and
maleimide
units
through
[3
+
2]
carbo-annulation
by
using
Ru-catalysis.
A
wide
range
maleimides
aroylsilanes
used
to
establish
broadness
these
transformations.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(5), С. 3214 - 3225
Опубликована: Фев. 21, 2024
Harnessing
the
organo-palladium
intermediates
generated
from
electrophilic
cyclizations
for
tandem
C–C
bond
construction
is
a
challenging
task
but
constitutes
an
excellent
tool
constructing
complex
motifs
simpler
substrates.
We
realize
herein
such
cyclative
annulation
of
alkynyl-oxime
ethers
with
maleimides
facile
isoxazole-phthalimide
hybrid
through
Pd(II)
catalysis.
This
protocol
features
regio-selectivity
in
C–H
selection,
broad
substrate
scope,
good
functional
group
tolerance,
and
scalability.
Necessary
KIE
&
labeling
studies
give
insight
into
reaction
mechanism.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(23), С. 16948 - 16964
Опубликована: Ноя. 16, 2021
A
Cu(I)-mediated
cascade
cyclization/annulation
of
unprotected
o-alkynylanilines
with
maleimides
in
one
pot
is
developed.
The
protocol
offers
sequential
formation
C–N
and
two
C–C
bonds
to
deliver
fused
benzo[a]carbazoles
having
free
NH
skeletons.
annulated
products
display
fluorescence
emission
the
range
485–502
nm
a
large
Stokes
shift
lifetime
∼17
ns.
3aa
displays
AEE
behavior
ethanol/hexane
system
possesses
marigold-flower-like
morphology
at
aggregated
state.
Cell
viability
assays
enumerate
biocompatible
AEEgens,
while
their
high
intracellular
depicts
cell
imaging
applicability.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
87(2), С. 1240 - 1248
Опубликована: Дек. 29, 2021
We
present
here
a
rhodium-catalyzed
oxidative
three-point
double
annulation
of
enaminones
with
propargylic
alcohols
via
C–H
and
C–N
bond
activation
to
access
arylnaphthalene-based
lignan
derivatives.
The
key
step
in
the
reaction
is
regioselective
insertion
alcohol
into
rhoda-cycle,
result
hydroxyl
rhodium
coordination.
Necessary
control
experiments
KIE
studies
were
conducted
determine
mechanism.
Chemical Communications,
Год журнала:
2022,
Номер
58(74), С. 10262 - 10289
Опубликована: Янв. 1, 2022
The
metal–carbon
bond
generated
through
C–H
activation
is
a
key
organometallic
intermediate,
which
could
be
further
functionalized
with
various
reacting
partners.
Among
the
coupling
partners
used
in
metal-catalysed
activation,
alkynes
occupy
prominent
position
on
account
of
their
varied
reactivity.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(9), С. 6551 - 6565
Опубликована: Апрель 26, 2021
A
ruthenium(II)-catalyzed
cross
dehydrogenative
annulation
of
N-(7-azaindole)benzamides
with
maleimides
has
been
demonstrated.
Herein,
we
have
explored
the
use
N-amino-7-azaindole
as
a
new
bidentate
directing
group
for
[4
+
2]
annulation.
This
method
works
efficiently,
affording
variety
pharmacologically
useful
7-azaindole-based
isoquinolones
and
showing
wide
functional
tolerance.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(6), С. 3834 - 3843
Опубликована: Фев. 29, 2024
Electrophilic
cyclization
and
concomitant
C–H
annulation
constitute
an
expedient
cascade
strategy
for
the
construction
of
multicyclic
scaffolds
with
precise
substitutional
patterns.
We
report
here
a
novel
Pd-catalyzed
cyclative
ynone
oxime
activated
alkynes.
The
features
dual
regioselectivity
including
site
selective
activation
chelation-assisted
insertion
Control
experiments
together
kinetic
give
insights
into
mechanism.
