ChemistryOpen,
Journal Year:
2021,
Volume and Issue:
10(5), P. 518 - 522
Published: Feb. 19, 2021
Abstract
Efficient
synthesis
of
N
,
O
‐heterocyclic
tetra‐substituted
trifluoromethyl‐3,1‐benzoxazines
via
a
transition‐metal‐catalyzed
decarboxylative
intramolecular
cyclization
was
achieved.
The
decarboxylation
‐benzoyl
trifluoromethyl‐benzoxazinones
generated
the
amide
oxygen
nucleophile,
allowing
selective
internal
C
1
‐attack
on
Pd‐
or
Cu‐coordinated
zwitterions,
affording
medicinally
attractive
vinyl‐
ethynyl‐trifluoromethyl‐3,1‐benzoxazines.
This
protocol
can
be
applied
to
perfluoroalkyl‐
and
non‐fluorinated
3,1‐benzoxazines.
ChemCatChem,
Journal Year:
2022,
Volume and Issue:
14(9)
Published: Jan. 31, 2022
Abstract
Palladium‐catalyzed
decarboxylative
cycloadditions
have
emerged
as
highly
effective
methods
for
constructing
structurally
diverse
carbo‐
and
heterocycles
because
of
the
formation
at
least
two
carbon‐carbon
or
carbon‐heteroatom
bonds
in
a
single
step.
It
is
great
interest
to
chemists
that
this
type
cycloaddition
reactions
possesses
some
special
advantages
such
high
reactivity,
exclusive
regioselectivity,
good
functional
group
compatibility.
Based
on
these
qualities,
palladium‐catalyzed
present
strong
ability
synthetic
chemistry
been
flourished
especially
last
five
years.
In
review,
achievements
involving
cyclic
carbonates,
carbamates,
lactones
accessing
oxacyclo‐,
azacyclo‐
carbocyclic
compounds
are
addressed.
Mechanistic
insights
applications
toward
synthesis
natural
products
discussed.
The
challenges
opportunities
field
also
outlined.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(18), P. 7158 - 7163
Published: Sept. 3, 2020
A
palladium/XantPhos-catalyzed
[5
+
2]
annulation
of
VECs
with
electron-deficient
alkenes
having
an
isolated
carbon–carbon
double
bond
has
been
developed
to
afford
spirobarbiturate-tetrahydrooxepines.
This
study
provides
expedient
assembly
biologically
interesting
The
easy
scalability
and
versatile
transformability
the
reaction
products
were
also
exhibited.
Chinese Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
42(10), P. 3051 - 3051
Published: Jan. 1, 2022
Chiral
heterocyclic
compounds
are
an
important
class
of
chiral
substances,
which
widespread
in
many
drugs,
pesticides
and
catalysts.Therefore,
the
efficient
asymmetric
synthesis
these
becomes
a
research
hotspot
organic
synthesis.Transition
metal-catalyzed
cyclization
with
heteroatom-dipole
precursors
is
method
to
construct
frameworks.Among
them,
designed
based
on
transition
allyl
or
propargyl
substitutions
have
been
extensively
studied
past
two
decades
occupied
role
this
field.The
cyclizations
introduced
detail.The
advantages
existing
problems
current
methods
analyzed,
would
provide
useful
reference
for
researchers
related
fields.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(7), P. 1561 - 1565
Published: Feb. 14, 2022
Alkynyl
esters
are
viable
dipolarophiles
for
the
palladium-catalyzed
asymmetric
(3
+
2)
cycloaddition
with
vinyl
epoxides.
The
chiral
dihydrofurans
obtained
in
high
yields
and
ee
values.
use
of
a
benzylic
substituted
P,N-ligand
is
essential.
usefulness
synthetic
method
has
been
demonstrated;
2,3-cis-tetrahydrofuran
was
also
provided.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(22), P. 3967 - 3972
Published: Oct. 18, 2022
Abstract
In
this
paper,
we
designed
and
synthesized
4‐vinyl‐4‐butyrolactone
as
a
precursor
to
generate
the
zwitterionic
allylpalladium
intermediates,
which
behaved
five‐membered
all‐carbon
synthon
in
palladium‐catalyzed
(5+3)
annulation
with
azomethine
imines,
giving
eight‐membered
ring‐fused
heterocycles
(26
examples,
49%
97%
yield,
>20:1
dr).
magnified
image
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 9, 2025
In
this
work,
we
developed
a
phosphine-catalyzed
cascade
lactonization/[2
+
1]
annulation
reaction
between
vinyl
oxiranes
and
sulfonium
compounds
for
the
highly
diastereoselective
construction
of
spiro-2(3H)-furanone
skeletons.
The
cycloaddition
proceeds
via
2(5H)-furanone
phosphonium
intermediate,
introducing
an
oxygen-containing
active
intermediate
phosphine
catalysis.
These
findings
highlight
significant
potential
harnessing
as
versatile
synthons
constructing
spirocyclic
through
simultaneous
multicyclic
skeleton
formation.
Organic & Biomolecular Chemistry,
Journal Year:
2020,
Volume and Issue:
18(48), P. 9826 - 9830
Published: Jan. 1, 2020
A
Pd-catalyzed
asymmetric
[5
+
2]
cycloaddition
reaction
was
developed
for
the
synthesis
of
N-fused
1,3-oxazepines
using
vinylethylene
carbonates
and
sulfamate-derived
cyclic
imines.
Under
mild
conditions,
a
series
optically
active
were
synthesized
in
good
yields
(up
to
89%)
enantioselectivities
90
:
10
er),
indicating
this
method
as
straightforward
approach
enantiomerically
enriched
1,3-oxazepine
derivatives.
The
synthetic
utility
presented
further
demonstrated
by
successful
transformation
resulting
useful
polycyclic
1,3-oxazepanes.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(46), P. 6646 - 6649
Published: Jan. 1, 2022
In
this
paper,
a
new
type
of
δ-vinylvalerolactone
was
designed
and
synthesized,
used
as
precursor
in
Pd-catalyzed
[6+3]
cycloaddition
with
azomethine
imines,
leading
to
nine-membered
1,2-dinitrogen-containing
heterocycles
77-98%
yields
>20
:
1
d.r.
These
ring-fused
products
were
further
transformed
into
unusual
tetracyclic
bridged-ring
compounds
without
loss
the
diastereoselectivities.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(76), P. 11298 - 11319
Published: Jan. 1, 2023
The
enantioselective
catalytic
cascade
involving
Tsuji-Trost
allylation
has
provided
a
viable
strategy
for
the
construction
of
multiple
asymmetric
C-C
and
C-X
centres
numerous
methods
have
been
developed
around
it
synthesis
various
vital
scaffolds.
synthetic
utility
this
was
enhanced
by
replacing
customary
allyl
acetates
with
ethylene
diacetates/dicarbonates,
vinyl
epoxides,
oxetanes,
carbonates,
cyclopropanes,
enynes,
dienes
using
transition-metal
catalysis.
One
more
milestone
achieved
when
metallaphotocatalysis
necessary
platform
these
cascades
cheaper
metal.
This
review
will
provide
summary
from
2015.
