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.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(9), С. 2554 - 2560
Опубликована: Янв. 1, 2024
A
three-component
one-pot
reaction
of
TMSCF
2
Br,
p
-QMs
and
1,3-dicarbonyl
compounds
derivatives
was
developed.
series
densely
functionalized
tetra-substituted
furans
pyrroles
were
constructed
with
excellent
chemoselectivities.
Chemical Science,
Год журнала:
2023,
Номер
15(2), С. 720 - 725
Опубликована: Дек. 2, 2023
Demonstrated
here
is
an
asymmetric
nucleophilic
addition
via
primary
activation
of
para
-quinone
methides
(
p
-QMs)
based
on
a
chiral
phosphoric
acid
catalytic
system.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(21), С. 4264 - 4268
Опубликована: Янв. 1, 2024
Herein,
we
describe
a
novel
metal-free
Brønsted
acid-catalyzed
Ficini
[2
+
2]
cycloaddition
of
ynamides
with
enones
under
mild
reaction
conditions,
leading
to
the
formation
various
cyclobutenamides
in
generally
good
excellent
yields
within
short
times.
This
work
represents
first
example
involved
nonmetal-catalyzed
enones.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16663 - 16678
Опубликована: Ноя. 1, 2024
A
novel
and
straightforward
method
for
the
iron-catalyzed
regioselective
cross-dehydrogenative
coupling
of
para-quinone
methides
(p-QMs)
with
formamides
has
been
developed,
facilitated
by
in
situ
activation
C(sp2)–H
bonds
formyl
alkenyl
substituents
via
a
radical
strategy.
This
does
not
require
preactivation
substrates,
it
can
accommodate
wide
range
p-QMs
under
optimized
reaction
conditions,
resulting
formation
expected
C-7
acetamides-functionalized
moderate
to
good
yields.
The
control
experiments
revealed
that
follows
fundamental
equation
second-order
kinetics.
Additionally,
an
exploration
Hammett
effect
was
undertaken
elucidate
impact
reaction.
In
combination
DFT
calculation,
plausible
mechanism
proposed
through
meticulously
controlled
experiments.
A
copper-catalyzed
[2,3]-sigmatropic
rearrangement
of
azide-ynamides
via
selenium
ylides
is
disclosed,
which
leads
to
the
practical
and
divergent
synthesis
a
variety
tricyclic
heterocycles
bearing
quaternary
carbon
stereocenter
in
generally
moderate
excellent
yields.
Significantly,
this
method
represents
first
ylide
based
on
alkynes
an
unprecedented
α-imino
copper
carbenes.
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.
