The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(15), С. 10916 - 10924
Опубликована: Июль 14, 2023
A
Rh(III)-catalyzed
[4
+
1]
cyclization
of
2-arylbenzimidazoles
with
alkynoates
through
C-H
activation/ortho-alkenylation/intramolecular
annulation
cascade
to
obtain
benzimidazole-fused
isoindoles
is
reported.
The
reaction
the
Rh
catalyst
and
internal
alkyne
ester
provides
benzo[4,5]imidazo[2,1-a]isoindole
acetate
exclusively.
Conversely,
amide
participates
in
process
presence
a
Ru
provide
acetamide.
acts
as
C1
synthon
undergoes
rather
than
traditional
2]
annulation.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(12), С. 2324 - 2338
Опубликована: Янв. 1, 2024
This
review
summarizes
the
most
recent
progress
made
in
C–H
bond
activation-initiated
spiroannulation
reactions
and
their
applications
construction
of
structurally
diverse
biologically
valuable
spirocyclic
scaffolds.
Chemical Communications,
Год журнала:
2022,
Номер
58(41), С. 6140 - 6143
Опубликована: Янв. 1, 2022
Highly
selective
and
switchable
[4+2]
annulations
of
2-arylindoles
with
iodonium
ylides
were
achieved
by
performing
solvent-controlled
Rh(III)-catalyzed
C-H
activations.
When
using
DCM
as
a
solvent,
the
functionalization
selectively
delivered
indolo[2,1-a]isoquinoline
derivatives.
In
contrast,
same
catalytic
system
polar
HFIP
solvent
predominately
provided
benzo[a]carbazole
moieties.
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.
European Journal of Organic Chemistry,
Год журнала:
2021,
Номер
2021(43), С. 5862 - 5879
Опубликована: Окт. 20, 2021
Abstract
Maleimides
and
succinimides
are
all
vital
scaffolds
in
biological
fields
various
natural
products.
Maleimide
derivatives
have
been
extensively
used
as
coupling
partners
for
organic
transformations,
affording
a
broad
array
of
important
molecular
architectures
including
succinimides.
In
the
past
decade,
variety
efficient
chelation‐assisted
strategies
employed
selective
addition
C−H
bonds
to
maleimides
giving
succinimides,
which
also
highly
building
blocks
synthesis.
This
Review
provides
an
overview
research
progress
relating
participated
transition‐metal‐catalyzed
group‐directed
alkylation
from
2012
2021.
Significant
advances
this
field
were
highlighted,
diverse
transition
metal
catalysts,
substrates
contained
different
directing
groups,
reaction
mechanisms
well
synthetic
applications
systematically
discussed.
addition,
limitations
intractable
issues
need
be
solved
future
pointed
out.
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.
ACS Catalysis,
Год журнала:
2024,
Номер
14(5), С. 2872 - 2882
Опубликована: Фев. 9, 2024
Readily
available
N-carbamoyl
indolines
can
be
converted
into
highly
valuable
2-alkenyl
and
2-alkyl
indoles
in
a
one-pot
reaction,
through
an
autotandem
catalytic
cascade
promoted
by
iridium
complex.
The
process
entails
dehydrogenation
reaction
initiated
iridium-promoted
C(sp3)–H
activation,
the
addition
of
resulting
indole
to
alkyne
-or
alkene-partner,
spontaneous
loss
carbamoyl
directing
group.
Interestingly,
C2-alkenyl
participate
variety
metal-catalyzed
annulations
C–H
including
formal
[4
+
1]
2]
cycloadditions,
as
well
cross-dehydrogenative
cyclizations,
thus
enabling
divergent
access
collection
functionally
rich
nitrogen-containing
heterocycles.
Chemical Communications,
Год журнала:
2021,
Номер
57(83), С. 10947 - 10950
Опубликована: Янв. 1, 2021
The
rhodium(III)-catalyzed
spiroannulation
reaction
between
N-aryl
indazol-3-ols
and
maleimides
is
described
herein.
developed
method
showcased
by
the
construction
of
spirosuccinimides
using
bioactive
molecule-linked
chemical
probe-linked
maleimides.
Combined
mechanistic
investigations
including
determination
an
isolable
rhodacycle
complex
aided
elucidation
a
plausible
mechanism.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(16), С. 10967 - 10981
Опубликована: Июль 28, 2022
Chemodivergent
synthesis
of
indeno[1,2-b]indoles
and
isoindolo[2,1-a]indoles
from
the
same
starting
materials
involving
radical
cross-dehydrogenative
couplings
have
been
developed.
Mn(OAc)3·2H2O
selectively
promoted
an
intramolecular
C–H/C–H
dehydrogenative
coupling
reaction
to
provide
indeno[1,2-b]indoles,
while
C–H/N–H
could
proceed
via
electrochemistry
deliver
isoindolo[2,1-a]indoles.
Plausible
mechanisms
chemodivergent
reactions
were
proposed.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2272 - 2282
Опубликована: Фев. 2, 2024
Synthesis
of
imidazo-fused
polyheterocyclic
molecular
frameworks,
viz.
imidazo[1,2-a]pyrrolo[3,4-e]pyridines,
imidazo[2,1-a]pyrrolo[3,4-c]isoquinolines,
and
benzo[g]imidazo[1,2-a]quinoline-6,11-diones,
has
been
achieved
by
the
ruthenium(II)-catalyzed
[4
+
2]
C–H/N–H
annulation
2-alkenyl/2-arylimidazoles
with
N-substituted
maleimides
1,4-naphthoquinones.
The
developed
protocol
is
operationally
simple,
exhibits
broad
substrate
scope
excellent
functional
group
tolerance,
provides
desired
products
in
moderate
to
good
yields.
mechanistic
studies
suggest
that
reaction
involves
formation
a
C–C
bond
through
Ru-catalyzed
C(sp2)–H
activation
followed
intramolecular
cyclization.
