Molecules,
Год журнала:
2023,
Номер
28(14), С. 5529 - 5529
Опубликована: Июль 20, 2023
An
unprecedented
N-alkylation
of
3-nitroindoles
with
para-quinone
methides
was
developed
for
the
first
time.
Using
potassium
carbonate
as
base,
a
wide
range
structurally
diverse
N-diarylmethylindole
derivatives
were
obtained
moderated
to
good
yields
via
protection
group
migration/aza-1,6-Michael
addition
sequences.
The
reaction
process
also
demonstrated
by
control
experiments.
Different
from
previous
advances
where
3-nitrodoles
served
electrophiles
trapping
various
nucleophiles,
herein
is
featured
that
defined
latent
N-centered
nucleophiles
react
ortho-hydrophenyl
p-QMs
construction
N-diarylmethylindoles.
Transition-metal-catalyzed
[2
+
2
2]
annulation
of
alkynes
is
an
efficient
pathway
for
the
synthesis
aromatic
compounds.
However,
most
established
methods
require
noble
metal
catalysts.
Herein,
we
report
a
copper-catalyzed
intermolecular
diynes
with
through
vinyl
cation
intermediates,
enabling
atom-economical
preparation
biologically
important
carbazole
skeletons.
The
reaction
shows
good
regioselectivity
in
aryl(alkyl)alkynes.
Moreover,
preliminary
results
have
also
been
obtained
related
catalytic
atroposelective
transformation.
This
represents
rare
example
non-noble-metal-catalyzed
ynamides
pathway.
Acta Chimica Sinica,
Год журнала:
2023,
Номер
81(7), С. 793 - 793
Опубликована: Янв. 1, 2023
o-Hydroxyphenyl
substituted
p-quinone
methides
(p-QMs)
belong
to
a
class
of
p-QMs
with
unique
advantages.They
not
only
maintain
the
high
reactivity
p-QMs,
but
also
have
more
reactive
and
activation
sites
owing
introduction
hydroxyl
group.Therefore,
o-hydroxyphenyl
wide
applications
in
synthetic
medicinal
chemistry.The
catalytic
asymmetric
1,6-conjugate
addition
[4＋n]
cycloaddition
developed
very
rapidly
recent
years,
which
become
efficient
strategies
for
synthesis
chiral
oxygen-containing
heterocycles
arylmethanes
potential
bioactivity.This
review
summarizes
reactions
involving
points
out
remaining
challenges
this
research
area,
will
open
new
window
design
type
their
involved
reactions.
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
new
strategy
for
the
construction
of
a
chiral
4-alkoxy-4
H
-chromene
skeleton
was
reported.
series
-chromenes
containing
trifluoromethyl
group
were
obtained
in
good
yields
and
excellent
enantioselectivity.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 31, 2025
In
this
work,
we
studied
the
conjugated
additions
of
bis-trimethylsilylacetalketene
acetals
(bis-TMSKA)
to
para-quinone
methides
(p-QMs),
which
are
one
most
explored
molecules
for
study
and
gained
significant
attention
in
organic
chemistry
due
their
versatile
reactivity,
particularly
Michael
addition
reactions.
study,
trifluoromethanesulfonic
anhydride
(Tf2O)
was
used
as
an
activating
agent
p-QMs,
aiming
achieve
1,6-Michael
products
least
reported
1,8-Michael
with
pyridine
substituents.
The
reactivity
p-QMs
derived
from
demonstrated
distinct
reaction
pathways,
leading
formation
δ
γ
lactones.
investigation
also
involved
synthesizing
a
1-indanone
carboxylic
acids
obtained
1,6-addition.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(11), С. 2766 - 2772
Опубликована: Янв. 1, 2023
An
efficient
and
controllable
cyclization
of
alkynyl
thioethers
via
Brønsted
acid-catalyzed
dearomatization
is
described,
enabling
practical
atom-economical
synthesis
valuable
spirohexenones
phenanthrols
in
generally
excellent
yields.
Communications Chemistry,
Год журнала:
2023,
Номер
6(1)
Опубликована: Сен. 12, 2023
Abstract
One-carbon
homologation
reactions
based
on
one-carbon
insertion
into
the
N−O
bond
of
heterocycles
have
received
tremendous
interest
over
past
decades.
However,
these
protocols
to
rely
use
hazardous
and
not
easily
accessible
diazo
compounds
as
precursors,
examples
relevant
asymmetric
catalysis
been
reported.
Here
we
show
that
a
copper-catalyzed
intermolecular
formal
(5
+
1)
annulation
1,5-diynes
with
1,2,5-oxadiazoles
involving
heterocyclic
via
non-diazo
approach.
This
method
enables
practical
atom-economic
synthesis
valuable
pyrrole-substituted
oxadiazines
in
generally
moderate
good
yields
under
mild
reaction
conditions.
In
addition,
possibility
such
an
also
emerges.
Synthesis,
Год журнала:
2024,
Номер
56(15), С. 2316 - 2328
Опубликована: Янв. 9, 2024
Abstract
The
atroposelective
transformation
of
alkynes
is
an
efficient
protocol
for
the
assembly
axially
chiral
compounds.
Benefitting
from
rapid
development
organocatalysts,
organocatalytic
reactions
have
been
extensively
studied
over
past
decades.
An
array
catalysts,
including
Brønsted
acid
secondary
amine
N-heterocyclic
carbene
(NHC)
thiourea
catalysts
and
N-squaramide
are
employed
in
enantioselective
different
alkynes.
This
short
review
summarizes
recent
advances
on
according
to
type
alkyne
substrate.
reaction
mechanisms,
modes
enantiocontrol,
product
diversity
applications
highlighted.
1
Introduction
2
Electron-Rich
Aryl
Alkynes
3
Electron-Deficient
4
Other
Types
5
Conclusion
Outlook
