Rh-Catalyzed α-Arylation of Cyclic 1,3-Dicarbonyls with Benzocyclobutenols Enabled by a Cyclic Iodonium Ylide Strategy
Organic Letters,
Год журнала:
2024,
Номер
26(20), С. 4383 - 4387
Опубликована: Май 14, 2024
To
date,
the
general
and
catalytic
α-arylation
of
cyclic
1,3-dicarbonyls
remains
elusive.
We
now
report
first
Rh-catalyzed
with
benzocyclobutenols
through
a
iodonium
ylide
strategy.
Our
strategy
represents
good
solution
for
previously
challenging
sterically
demanding
aryl
partners,
which
is
especially
appropriate
structurally
unique
heteroaromatic
1,3-dicarbonyls.
approach
features
mild
conditions,
readily
available
starting
materials,
high
yields,
excellent
functional
group-tolerance,
simple
operation,
providing
expedient
access
toward
medically
important
2-aryl
(hetero)cyclic
The
practicality
this
demonstrated
by
gram-scale
synthesis,
one-pot
numerous
downstream
transformations.
Язык: Английский
Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 5, 2025
A
tandem
Hexadehydro-Diels–Alder
(HDDA)/[2
+
2]
cycloaddition/aryl
migration
reaction
of
iodonium
ylide
with
tetrayne
is
described,
in
which
served
as
a
unique
double
bond
and
reacted
aryne
to
form
four-membered
iodonium(III)
cycle,
then
converted
iodoarene
after
aryl
group
from
iodine
adjacent
carbon.
This
strategy
allows
the
efficient
construction
fully
substituted
compounds.
Язык: Английский
Recent Advances in the Synthesis of Nitrogen‐Containing Heterocycles Based on Hydrazine‐Directed C−H Bond Activation/Annulation Reactions
European Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 21, 2025
Abstract
Nitrogen‐containing
heterocyclic
compounds
are
the
core
skeletons
of
many
natural
products,
bioactive
molecules
and
drugs,
transition
metal‐catalyzed
hydrazine‐directed
C−H
bond
activation/annulation
reactions
is
one
effective
methods
for
synthesis
nitrogen‐containing
compounds.
In
this
review,
important
research
progress
activation
reviewed
according
to
size
constructed
heterocycles,
substrate
scope
reaction
mechanism
discussed
in
detail,
limitations
future
development
prospects
summarized
outlooked.
Язык: Английский
Synthesis of 1-Aminoisoquinolines via Rh(III)-Catalyzed C–H Cascade Annulation of Benzamidines with Iodonium Ylides
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 10, 2025
A
Rh(III)-catalyzed
C-H
cascade
annulation
reaction
of
benzamidine
hydrochlorides
with
iodonium
ylides
has
been
successfully
accomplished,
providing
an
efficient
strategy
for
the
synthesis
various
1-aminoisoquinoline
derivatives
in
moderate
to
good
yields.
Here,
ylide
serves
as
accessible
and
safe
carbene
precursor.
Further
derivatizations
were
implemented
demonstrate
potential
utility
this
reaction.
Furthermore,
photophysical
properties
these
compounds
may
have
applications
photoelectric
materials.
Язык: Английский
Rh-Catalyzed Coupling of Cyclic 1,3-Dicarbonyl-Derived Iodonium Ylides with Cyclopropanols
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 10, 2025
Herein,
we
report
a
modular
α-monoalkylation
of
cyclic
1,3-dicarbonyls
with
cyclopropyl
alcohols
through
iodonium
ylide
strategy.
This
approach
is
general,
base-free,
operationally
simple,
and
suitable
for
various
medically
important
(hetero)cyclic
1,3-dicarbonyls.
A
wide
range
alcohols,
easily
prepared
from
feedstock
chemicals,
can
serve
as
complement
alkylating
agents.
Importantly,
the
newly
formed
carbonyl
groups
in
resulting
products
provide
versatile
platform
numerous
synthetic
applications.
Язык: Английский
Rhodium(III)-Catalyzed C–H Activation/[5 + 2] Cascade Annulation of Aroyl Hydrazides with Iodonium Ylides for the Synthesis of Seven-Membered Dibenzodiazepinediones
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 30, 2024
A
novel
Rh(III)-catalyzed
C-H
activation/[5
+
2]
cascade
annulation
of
aroyl
hydrazides
with
iodonium
ylides
is
accomplished,
in
which
diverse
seven-membered
dibenzodiazepinediones
were
afforded
moderate
to
excellent
yields.
This
reaction
features
an
ideal
functional
group
tolerance
and
a
wide
substrate
scope.
Large-scale
derivatization
reactions
conducted
demonstrate
the
potential
utility
this
transformation.
Язык: Английский
Cyclic Iodonium Ylide Unlocked Pd-Catalyzed α-Acyloxylation of Cyclic 1,3-Dicarbonyls with Carboxylic Acids
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 10, 2024
To
date,
a
general
approach
for
the
direct
α-acyloxylation
of
cyclic
1,3-dicarbonyls
remains
challenging.
Herein,
we
report
Pd-catalyzed
1,3-dicarbonyl-derived
hypervalent
iodine
compounds
with
highly
abundant
carboxylic
acids.
Our
utilizes
commercially
available
Pd(OAc)
Язык: Английский
Synthesis of 4-(trifluoromethyl)thiocoumarins
Russian Chemical Bulletin,
Год журнала:
2024,
Номер
73(10), С. 3045 - 3054
Опубликована: Окт. 1, 2024
Язык: Английский
Rh(III)-Catalyzed Aminoalkylation of Alkenes with Diazo Compounds toward Functionalized Isoindolinones
Chinese Journal of Organic Chemistry,
Год журнала:
2024,
Номер
44(11), С. 3505 - 3505
Опубликована: Янв. 1, 2024
Язык: Английский
Bioinspired Synthesis of Phelligridin Analogues via Ru-Catalyzed C–H Activation/[4 + 2] Annulation of Aryl Imidates with Heteroaromatic Iodonium Ylides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 16, 2024
The
first
Ru(II)-catalyzed
C–H
activation/[4
+
2]
annulation
of
aryl
imidates
with
heteroaromatic
iodonium
ylides
is
reported.
Our
approach
features
the
utilization
a
commercially
available
ruthenium
catalyst,
providing
one-step
construction
phelligridin
analogues
from
easily
and
nonpreactivated
starting
materials.
developed
methodology
successfully
employed
for
total
synthesis
A,
significantly
streamlining
previous
multistep
synthesis.
potential
this
further
demonstrated
through
modular
core
structure
C/D.
Язык: Английский