The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8363 - 8375
Опубликована: Июнь 7, 2024
Palladium-catalyzed
decarboxylation
of
5-methylene-1,3-oxazinan-2-ones
and
5-methylene-1,3-dioxan-2-ones
to
generate
aza-π-allylpalladium
oxa-π-allylpalladium
1,4-dipoles
for
[4
+
2]
cycloaddition
reaction
with
1,3,5-triazinanes
was
developed,
affording
a
wide
range
hexahydropyrimidine
1,3-oxazinane
derivatives
in
good
excellent
yields
(up
99%).
The
acyclic
sulfonamido-substituted
allylic
carbonates
as
1,4-dipole
precursors
also
apply
the
developed
synthesized
strategy,
achieving
synthesis
hexahydropyrimidines.
Moreover,
situ-generated
undergoing
dimeric
4]
were
demonstrated
by
construction
1,5-diazocane
derivatives.
Oxepino[b]indoles
were
obtained
in
good
to
excellent
yields
employing
a
[4
+
3]-cycloaddition
initiated
by
stereo-
and
regioselective,
RhII-catalyzed
cyclopropanation
between
vinyl
allene
diazooxindole
afford
an
intermediate
cyclopropyl
that
engaged
the
oxindole
carbonyl
spontaneous
hetero-[3,3]-rearrangement.
A
survey
of
functional
group
tolerance
revealed
diverse
array
substrates
amenable
oxepino[b]indole
formation.
In
addition
intriguing
architecture
cycloadducts,
exposure
either
Brønsted
acid
or
base
enables
assembly
functionalized
spirroxindoles
via
unusual
conversion
5-7
fused
ring
system
5-5
spirocycle.
Beilstein Journal of Organic Chemistry,
Год журнала:
2025,
Номер
21, С. 890 - 914
Опубликована: Май 7, 2025
The
development
of
streamlined
methodologies
for
the
expeditious
assembly
structurally
diverse
organic
architectures
represents
a
paramount
objective
in
contemporary
synthetic
chemistry,
with
far-reaching
implications
across
pharmaceutical
development,
advanced
materials
innovation,
and
fundamental
molecular
science
research.
In
recent
years,
controllable/divergent
strategies
functional
molecules
using
common
starting
have
garnered
significant
attention
due
to
their
high
efficiency.
This
review
categorizes
literatures
focusing
on
key
regulatory
factors
product
divergent
formation,
which
controlling
chemical
selectivity
primarily
relies
ligands,
metal
catalysts,
solvents,
time,
temperature,
acids/bases,
subtle
modifications
substrates.
To
gain
deeper
understanding
mechanisms
underlying
reaction
activity
differentiation,
provides
systematic
analysis
critical
steps
through
specific
case
studies.
It
is
hoped
that
synthesis
concept
will
spark
interest
practitioners
aficionados
delve
into
discipline
pursue
novel
advancements
realm
synthesis.
Organic Letters,
Год журнала:
2024,
Номер
26(7), С. 1483 - 1488
Опубликована: Фев. 12, 2024
Presented
herein
is
a
palladium-catalyzed
asymmetric
(3
+
2)
annulation
reaction
between
1,3-dienes
and
2-formylarylboronic
acids,
proceeding
in
cascade
vinylogous
addition
Suzuki
coupling
process.
Both
electron-neutral
electron-deficient
are
compatible
under
similar
catalytic
conditions,
distinct
regioselectivity
observed
via
functional-group
control
of
1,3-diene
substrates.
A
collection
1-indanols
with
dense
functionalities
constructed
stereoselectively.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8951 - 8959
Опубликована: Май 30, 2024
Palladium-catalyzed
(4
+
1)
annulation
of
4-vinylbenzodioxinones
with
sulfur
ylides
has
been
developed
to
afford
various
dihydrobenzofuran
derivatives
in
moderate
high
yields
excellent
diastereoselectivities.
The
scale-up
reaction
and
further
derivations
the
product
worked
well,
demonstrating
application
potential
current
organic
synthesis.
ACS Catalysis,
Год журнала:
2024,
Номер
14(17), С. 12824 - 12832
Опубликована: Авг. 10, 2024
Here,
we
demonstrate
that
Pd(0)
can
undergo
direct
oxidative
addition
to
electron-deficient
1-azadienes
without
the
additional
assistance
of
Lewis
or
Bro̷nsted
acids,
and
resultant
azapalladacycle
species
undertake
migratory
insertion
into
allenes
with
exclusive
C2-regioselectivity.
Fine
dynamic
kinetic
transformation
is
achieved
in
subsequent
N-allylic
alkylation
situ
formed
π-allylpalladium
intermediates
from
racemic
allenes,
high
levels
enantioselectivity
are
generally
obtained
for
tetrahydropyridine
products
an
E-exo-double
bond
a
(4
+
2)
annulation
pattern.
Moreover,
switchable
regiodivergent
1)
annulations
different
types
be
accomplished
via
ligand
control.
In
addition,
similar
oxapalladacycles
activated
enones
generated
assembled
access
dihydropyran
derivatives
enantioselectively,
further
enriching
diversity-oriented
synthesis.
An
array
control
experiments
spectroscopic
analyses
conducted
confirm
formation
these
unusual
heteropalladacycle
intermediates,
density
functional
theory
(DFT)
calculations
carried
out
illuminate
catalytic
pathways.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(19), С. 5495 - 5501
Опубликована: Янв. 1, 2024
Rhodium(
i
)-catalyzed
sequential
decarboxylation
and
hydroacylation
of
vinyl
benzoxazinanones
with
chelating
aldehydes
for
the
highly
regioselective
synthesis
2-substituted
indolines
via
a
new
η
2
-Rh
complex
has
been
developed.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
13(1)
Опубликована: Ноя. 28, 2023
Abstract
A
regioselective
annulation
protocol
of
N
‐chlorobenzamide
with
allenes
and
vinyl
acetate
is
reported
using
a
less
expensive
catalytic
system,
i.
e
.
Co(III)
catalysis
Na
2
CO
3
as
base.
(CO)
NH−Cl
acts
both,
an
internal
oxidant
directing
group.
Allenes
are
successfully
annulated
‐chlorobenzamide,
providing
different
exocyclic
isoquinolone
derivatives
in
good
to
moderate
yield.
Notably,
acetylene
surrogate
undergoes
the
developed
provide
excellent
Interestingly,
situ
deprotection
acetyl
group
allowed
quantitative
synthesis
hydroxyisoquinolone.
Chemical Communications,
Год журнала:
2024,
Номер
60(76), С. 10516 - 10519
Опубликована: Янв. 1, 2024
Pd-catalyzed
sequential
intramolecular
annulation/intermolecular
[3+2]
cycloaddition
of
5-allenyloxazolidine-2,4-diones
with
dipoles
was
achieved.
Under
palladium
catalysis,
various
reacted
1,3-dipoles
such
as
nitrile
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8363 - 8375
Опубликована: Июнь 7, 2024
Palladium-catalyzed
decarboxylation
of
5-methylene-1,3-oxazinan-2-ones
and
5-methylene-1,3-dioxan-2-ones
to
generate
aza-π-allylpalladium
oxa-π-allylpalladium
1,4-dipoles
for
[4
+
2]
cycloaddition
reaction
with
1,3,5-triazinanes
was
developed,
affording
a
wide
range
hexahydropyrimidine
1,3-oxazinane
derivatives
in
good
excellent
yields
(up
99%).
The
acyclic
sulfonamido-substituted
allylic
carbonates
as
1,4-dipole
precursors
also
apply
the
developed
synthesized
strategy,
achieving
synthesis
hexahydropyrimidines.
Moreover,
situ-generated
undergoing
dimeric
4]
were
demonstrated
by
construction
1,5-diazocane
derivatives.
