Organic Letters,
Год журнала:
2024,
Номер
26(9), С. 1908 - 1913
Опубликована: Фев. 26, 2024
An
intermolecular
controllable
Pd-catalyzed
spirocyclization
of
isocyano
cycloalkenes
has
been
developed,
offering
efficient
and
selective
approaches
toward
spirocyclic
hydropyrrole
scaffolds.
2-Azaspiro-1,7-dienes
could
be
obtained
through
a
"chain-walking"
process
with
aryl/vinyl
iodides
as
electrophiles,
while
the
normal
Heck
product
2-azaspiro-1,6-dienes
were
selectively
generated
when
aryl
triflates
used
coupling
partner
isocyanides.
Mechanistic
studies
suggested
that
counteranion
Pd(II)
intermediate
played
crucial
role
in
regioselectivity
control.
Dihydropyrrole-fused
5,6,7-membered
spirocycles
switchably
accessed
under
mild
conditions
wide
functional
group
tolerance.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(10), С. 1128 - 1132
Опубликована: Фев. 6, 2024
Comprehensive
Summary
A
mild
and
practical
method
for
synthesizing
fluorinated
quinoline
derivatives,
which
have
a
wide
range
of
applications
in
pharmaceuticals,
materials,
organic
synthesis,
was
described
through
C—F
bond
insertion
into
indoles
using
CHBr
2
F.
The
simple
conditions,
readily
availability
F,
as
well
the
versatility
transformations
make
this
strategy
very
powerful
3‐fluoroquinoline
3‐fluoroquinolone.
mechanistic
studies
reveal
that
bromofluorocarbene
generated
in‐situ
under
basic
condition
key
intermediate.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(11), С. 3250 - 3256
Опубликована: Янв. 1, 2024
An
unusual
visible-light-induced
[1,3]-brook
rearrangement
of
α-ketoacylsilanes
for
cascade
cyclization
with
1,3,5-triazinanes
and
C
,
N
-cyclic
azomethine
imines
has
been
realized
to
assemble
various
β-lactams
pyrazolidinone
scaffolds.
Organic Letters,
Год журнала:
2021,
Номер
23(19), С. 7342 - 7347
Опубликована: Сен. 15, 2021
A
divergent
reaction
of
isocyanides
with
o-bromobenzaldehydes
for
the
synthesis
isoindolinone-derived
ketenimines
and
lactams
was
disclosed.
The
features
readily
available
reactants,
relatively
mild
conditions,
high
yields
products.
Ketenimines
could
be
applied
in
further
transformations
access
to
other
functional
molecules.
mechanism
study
showed
that
palladium-migration/imine-insertion
process
key
step
this
reaction.
Organic Letters,
Год журнала:
2021,
Номер
23(17), С. 6740 - 6744
Опубликована: Авг. 12, 2021
A
Co-catalyzed
cyclization
reaction
of
isocyanides,
azides,
and
amines
to
access
quinazoline
derivatives
was
described.
This
protocol
features
a
high
atom
economy,
mild
conditions,
excellent
yields,
broad
substrate
scope.
cascade
involved
three
or
four
C–N
bonds
the
formation
one
two
rings.
The
quinazolin-4(H)-imines
obtained
are
proven
be
versatile
intermediates
for
further
valuable
transformations.
It
also
found
that
cobalt
catalyst
could
isolated
from
mixture
reused.
Chemical Communications,
Год журнала:
2021,
Номер
57(81), С. 10576 - 10579
Опубликована: Янв. 1, 2021
A
palladium-catalysed
construction
of
spiroindolines
through
dearomative
spirocyclization
3-(2-isocyanoethyl)indoles
has
been
developed.
2'-Aryl-,
vinyl-,
and
alkyl-substituted
could
be
accessed
under
mild
conditions
with
excellent
functional
group
tolerance.
C1-tethered
oxindole-
indole-spiroindoline
bisheterocycles
were
generated
in
high
yields
via
alkene/allene
insertion
an
imidoylative
cascade.
Additionally,
a
tandem
dearomatization
two
different
indoles
was
realized
N-(2-bromobenzoyl)indoles
as
the
electrophilic
coupling
partner
3-(2-isocyanoethyl)indoles,
affording
polyindoline
-
spiroindoline
bisheterocyclic
scaffolds
conveniently.
Under
catalysis
Pd(OAc)2
spinol-derived
phosphoramidite
ligand,
chiral
successfully
up
to
95%
yield
85%
ee.
Organic Letters,
Год журнала:
2023,
Номер
25(27), С. 4956 - 4961
Опубликована: Июнь 29, 2023
A
novel
and
unprecedented
p-toluenesulfonic
acid-catalyzed
dehydrative
Nazarov-type
cyclization/C2-N1
bond
cleavage
cascade
reaction
of
perfluoroalkylated
3-indolyl(2-benzothienyl)methanols
has
been
developed.
This
provides
an
efficient
practical
protocol
for
the
construction
highly
functionalized
benzothiophene-fused
cyclopentenones
with
exclusive
stereoselectivity.
In
addition,
this
transformation
also
delineates
a
rare
example
involvement
selective
C2-N1
indoles.
Nature Communications,
Год журнала:
2025,
Номер
16(1)
Опубликована: Май 26, 2025
N-trifluoromethyl
compounds,
featuring
a
CF3
group
directly
attached
to
nitrogen,
are
valuable
in
medicinal
chemistry.
Despite
substantial
advances
their
synthesis
over
the
past
decade,
efficient
preparation
of
inherently
unstable
N-CF3
secondary
amines
remains
challenge
synthetic
Herein,
we
present
mild
and
practical
method
for
synthesizing
these
compounds
via
oxidative
fluorination
isocyanides
using
iodine
as
oxidant,
silver
fluoride
fluorinating
reagent,
tert-butyldimethylsilane
proton
precursor.
This
approach
benefits
from
simple
workup,
all
reagents
by-products
can
be
easily
removed
through
filtration
evaporation.
protocol
features
broad
substrate
scope,
good
functional
tolerance,
excellent
yields.
Additionally,
resulting
products
readily
converted
into
carbamoyl
fluorides,
building
blocks
diverse
carbonyl
derivatives.
Organic Letters,
Год журнала:
2022,
Номер
24(32), С. 6006 - 6012
Опубликована: Авг. 5, 2022
A
novel
four-component
reaction
of
alkynes,
amines,
azides,
and
2H-azirines
has
been
developed
for
the
first
time
by
efficient
formation
four
C–N
bonds
in
one
step
under
mild
conditions,
rapidly
preparing
polyfunctionalized
triazoles
with
molecular
diversity
involving
three
different
intermediates
copper–acetylide,
copper–allenylidene,
copper–vinyl
nitrene.
Propargylic
ester
is
disclosed
as
a
"three-in-one"
building
block
possessing
triplicate
cycloaddition
nucleophilic
electrophilic
properties,
which
could
enable
such
transformation
high
yields,
broad
substrate
scope,
functionalization.
