Rhodium-Catalyzed Tandem Reaction of N-(Pivaloyloxy)acrylamides with 1,3-Diynes for the Synthesis of Furo[2,3-b]pyridines
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 19, 2025
We
disclose
a
rhodium-catalyzed
tandem
reaction
of
N-(pivaloyloxy)acrylamides
with
1,3-diynes
for
the
efficient
synthesis
furo[2,3-b]pyridines.
This
unique
includes
C-H
activation,
Lossen
rearrangement,
[4+2]
annulation,
and
[3+2]
annulation
in
"one
pot",
which
features
readily
available
substrates,
broad
functional
group
compatibility,
ability
to
isolate
pure
products
through
simple
filtration
under
ambient
conditions
excellent
regioselectivity,
selectivity
mono-
or
diannulation,
intra-
intermolecular
selectivity.
Furthermore,
this
synthetic
protocol
facilitates
rapid
construction
diverse
library
blue-emitting
molecules
high
quantum
yields,
providing
valuable
platform
developing
advanced
materials.
Language: Английский
DFT Investigation on Palladium-Catalyzed [2 + 2 + 1] Spiroannulation between Aryl Halides and Alkynes: Mechanism, Base Additive Role, and Solvent and Ligand Effects
Xue Tan,
No information about this author
Wenji Bai,
No information about this author
Yu-Bing Shi
No information about this author
et al.
The Journal of Physical Chemistry A,
Journal Year:
2024,
Volume and Issue:
128(42), P. 9135 - 9145
Published: Oct. 11, 2024
Transition
metal-catalyzed
spiroannulations
are
practical
strategies
for
constructing
spirocyclic
skeletons
of
pharmaceutical
and
biological
significance,
yet
the
microscopic
mechanism
still
lacks
in-depth
explorations.
Here,
palladium-catalyzed
[2
+
2
1]
spiroannulation
between
aryl
halides
alkynes
was
studied
by
employing
density
functional
theory
(DFT)
method.
Based
on
comprehensive
explorations
a
couple
possible
reaction
pathways,
it
is
found
that
probably
experiences
C-I
oxidative
addition,
alkyne
migration
insertion,
Cs
Language: Английский