The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14435 - 14444
Published: Sept. 28, 2023
A
novel
palladium-catalyzed
intermolecular
dearomatization
of
furans
with
alkynes
via
a
three-component
formal
[3
+
2]
spiroannulation/allylic
substitution
cascade
reaction
has
been
successfully
developed
for
the
stereoselective
assembly
spiro
2,5-dihydrofuran
frameworks.
High
step
economy
and
efficacy
as
well
excellent
stereoselectivity
were
achieved
broad
substrate
scope.
Two
new
C-C
bonds
one
C-O
bond
generated
sequentially
in
one-pot
manipulation.
The
yielded
skeleton
bearing
tetrasubstituted
carbon
center
constitutes
core
structure
plenty
useful
natural
products
or
corresponding
analogues.
This
work
represents
significant
advancement
strategy
furan
heterocycles
provides
practical
methodology
expedited
access
to
complex
dihydrofuran
scaffolds.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(19), P. 13610 - 13621
Published: Sept. 11, 2023
An
electrophilic
spirocyclization
of
N-benzylacrylamides
with
N-halosuccinimides
(NXS)
as
the
halogenating
reagents
has
been
developed.
This
reaction
is
carried
out
at
room
temperature
under
simple
conditions
without
relying
on
metal
reagents,
photochemistry,
or
electrochemistry,
providing
a
fast
and
efficient
route
to
synthesize
wide
variety
4-halomethyl-2-azaspiro[4.5]decanes
satisfactory
yields.
The
approach
further
highlighted
through
gram-scale
synthesis
diverse
transformations
spiro
products.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(8), P. 2827 - 2832
Published: Jan. 1, 2024
Efficient
control
over
several
possible
reaction
pathways
of
free
radicals
is
the
chemical
basis
their
highly
selective
transformations.
Among
various
competing
pathways,
sulfonimidyl
generated
from
electrolysis
2-alkynylbenzenesulfonamides
undergo
cascade
migratory
or
Tetrahedron Chem,
Journal Year:
2024,
Volume and Issue:
9, P. 100055 - 100055
Published: Jan. 14, 2024
This
review
concentrates
on
our
research
into
the
discovery
of
novel
ynone-based
dearomative
spirocyclisation
processes,
whilst
placing
new
chemistry
context
existing
knowledge.
The
genesis
programme,
development
efficient
synthetic
routes
to
prepare
natural
products
spirobacillene
A
(1)
and
B
(2),
utilised
indole
ynones.
stimulated
a
much
wider
study
explore
reactivity
ynones
in
processes
more
generally.
Routes
generate
wide
range
spirocycles
were
subsequently
developed,
with
reactions
tethered
indoles,
benzofurans,
benzisoxazoles,
pyrroles,
pyridines,
isoquinolines,
pyrazines,
cyclic
ketimines,
anisoles
all
discussed
herein,
these
initiated
by
catalytic
Ag(I),
Cu(II),
Pd(0),
photolysis
many
other
reagents.
Asymmetric
variants
some
are
also
discussed,
as
is
further
elaboration
spirocyclic
give
carbazoles,
quinolones,
polycycles
useful
building
blocks.
Finally,
applications
methodology
product
synthesis
(e.g.
A,
lasubine
II
indolizidine
209D)
described.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(32), P. 6001 - 6005
Published: Aug. 7, 2023
An
electrochemical
facilitated
three-component
trifluoromethylation/spirocyclization
reaction
of
N-(arylsulfonyl)acrylamides,
CF3SO2Na,
and
H2O
has
been
developed.
Without
the
requirement
chemical
oxidants,
a
number
unexplored
trifluoromethylated
4-azaspiro[4.5]decanes
were
obtained
in
satisfactory
yields
under
mild
conditions.
This
work
provides
new
synthetic
strategy
for
fluorine-containing
spirocyclic
compounds
shows
perspective
reactivity
study
N-(arylsulfonyl)acrylamides.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(4), P. 2200 - 2211
Published: Feb. 8, 2024
Electrochemical
dearomatization
has
been
recognized
as
an
attractive
tool
for
the
rapid
construction
of
structurally
diverse
molecules.
The
designed
methodology
encompasses
eco-friendly
and
efficient
electrochemical
approach
to
synthesizing
spiro[4.5]dienones
under
mild
reaction
conditions.
Furthermore,
detailed
mechanistic
studies
strongly
bolster
our
hypothesis
emphasize
role
HFIP
in
mechanism.
protocol
is
scalable
showcases
a
broad
substrate
scope
with
tolerance
toward
numerous
functional
groups.
Henceforth,
this
strategy
can
be
deployed
alternative
sustainable
accessing
spiro[4.5]dienones.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(35), P. 7330 - 7335
Published: Aug. 22, 2024
Synthesis
of
diversely
functionalized
quinoline-2-carboxylates
is
illustrated
through
electrochemical
cross-dehydrogenative
coupling
between
N-aryl
glycinates
and
methylenecyclopropanes.
An
extensive
range
distinct
functionalities
well-compatible
under
these
transition-metal-
oxidant-free
mild
conditions,
contributing
to
a
broad
substrate
scope
practical
applicability.
Cyclic
voltammetric
measurements
control
experiments
suggested
formal
[4
+
2]
cycloaddition
involving
radical
intermediates,
followed
by
cyclopropyl
ring
opening
nucleophilic
polar
addition,
consecutively
fabricating
C–C
C–N
bonds.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(23), P. 16485 - 16496
Published: Nov. 9, 2023
Till
date,
the
ipso-cyclization
of
propiolamides
is
limited
to
provide
azaspiro[4,5]decatrienones.
Herein,
we
present
first
example
ipso-carbocyclization,
leading
azaspiro[5,5]-undecatrienones
from
N-propiolyl-2-arylbenzimidazoles,
involving
both
radical-based
and
electrophilic
reactions.
This
report
establishes
an
access
a
wide
range
chalcogenated
(SCN/SCF3/SePh)
benzimidazo-fused
azaspiro[5,5]undecatrienones
in
good
yields.
The
reaction
of
N
-propiolyl-benzimidazole
with
aliphatic
carboxylic
acids
in
the
presence
ammonium
persulfate
leading
to
pyrrolo-benzimidazolones
is
presented.
