Abstract
We
developed
a
temperature‐controlled
intermolecular
dearomative
[5+1]
spiroannulation
and
[5+2]
cyclization
of
indoles
with
enynones,
smoothly
delivering
variety
spiroindolenines
dihydrocyclohepta[
b
]indolones
under
40
°C
80
°C,
respectively.
A
three‐step
cascade
reaction
was
also
realized
by
using
OTBS
or
NHBoc
containing
enynones
in
the
indole
identical
condition.
And
novel
valuable
highly‐oriented
three‐dimensional
indole‐based
tetracyclic
scaffold
produced
high
yields
excellent
diastereoselectivities.
Additionally,
various
spiroindolines
spirooxindoles
were
facilely
through
simple
operations.
This
highly
efficient
domino‐reaction
represents
an
emblematic
method
for
preparation
polycycles
pathway.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(18), P. 5041 - 5052
Published: Jan. 1, 2022
This
review
highlights
the
encouraging
advances
in
hydride
transfer-involved
dearomatization
reaction
during
past
decade,
content
of
which
is
categorized
according
to
acceptors,
namely
vinylogous
imines
and
quinone
methides.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(13), P. 5134 - 5141
Published: Jan. 1, 2023
The
H
2
O-promoted
controllable
synthesis
of
diverse
3-carboxyl
and
3-acyl
substituted
tetrahydroquinolines
3,4-dihydroquinolin-2(1
)-ones
from
readily
available
feedstocks
was
developed
by
a
hydride
transfer
strategy.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(14), P. 2432 - 2437
Published: April 5, 2023
An
unprecedented
hydride
transfer-triggered
cross-dehydrogenative
coupling
of
two
C(sp3)-H
bonds
to
target
nine-membered
rings
has
been
developed.
Salient
features
this
methodology
include
atom
and
step
economy
metal-free
redox-neutral
conditions,
with
water
as
the
byproduct
proceeding
well
even
decomposed
aldehydes.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(7), P. 1796 - 1802
Published: Jan. 1, 2023
An
aromatization-driven
hydride
transfer-involved
α-C(sp
3
)–H
bond
functionalization
of
the
oxygen
atom
was
developed.
Easily
prepared
p
-quinone
methides
were
applied
to
initiate
[1,5]-hydride
transfer/cyclization
for
generating
spirochromanes.
Green Synthesis and Catalysis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Feb. 1, 2024
1,7-Hydride
transfer-involved
dearomatization
of
quinolines
toward
C3-spiro
hydroquinoline
derivatives
has
been
developed.
This
method
offers
a
protocol
to
achieve
the
electron-deficient
arenes
via
redox-neutral
hydride
transfer
process.
A
series
hydroquinolines
can
be
provided
in
moderate
excellent
yields
(up
98%)
with
good
diastereoselectivities.
Significant
advantages
such
as
high
step-
and
atom-economy,
well
mild
conditions,
make
it
an
appealing
alternative
quinolines.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(11), P. 7290 - 7301
Published: May 17, 2023
A
novel
and
streamlined
approach
to
synthesizing
benzotriazepin-1-ones
has
been
developed
through
a
hexafluoroisopropanol-promoted
decarboxylative
cascade
reaction
between
isatoic
anhydrides
hydrazonoyl
chloride.
The
[4
+
3]
annulation
of
hexafluoroisopropyl
2-aminobenzoates
with
nitrile
imines,
generated
in
situ,
is
key
feature
this
innovative
reaction.
This
offered
simple
efficient
method
for
broad
range
structurally
intricate
highly
functional
benzotriazepinones.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(13), P. 8791 - 8801
Published: June 1, 2023
A
[6
+
1]
annulation
reaction
via
cascade
1,6-hydride
transfer/cyclization
is
reported
to
construct
a
polycyclic
3,4-fused
azepinoindole
skeleton.
The
newly
designed
4-amino-indole-3-carbaldehyde
applied
as
novel
six-atom
synthon,
interacting
with
arylamines
and
malononitrile
achieve
the
annulation.
Notably,
proceeds
smoothly
under
redox-neutral
metal-free
conditions,
providing
wide
range
of
azepinoindoles
in
up
94%
yields,
water
only
byproduct.
Besides,
advantage
high
step-
atom-economy
further
highlights
practicality
this
methodology.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(47), P. 8709 - 8713
Published: Nov. 18, 2022
The
diastereoselective
assembly
of
spiroindolenines
via
a
synergistic
scandium/gold-catalyzed
dearomative
spiroannulation
is
herein
described.
This
protocol
offers
access
to
wide
variety
spiroindolenine
derivatives
in
86%
average
yield
with
moderate
excellent
diastereoselectivities
(up
97:3
dr).
control
experimental
studies
lend
support
the
bimetallic
relay
catalysis.
Moreover,
scale-up
reaction
and
synthetic
transformations
product
further
demonstrate
its
utility.
