Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(70)
Published: Oct. 11, 2023
Although
challenging,
the
distant
C-H
functionalization
with
precision
is
quite
rewarding
and
has
long
been
intriguing.
Tailoring
an
appropriate
template
accomplishes
job
but
prerequisite
sets
limitation.
We
herein
unveil
our
discovery
of
annulation
alkynes
on
to
two
(from
directing
group)
bonds
through
rollover
cyclometallation
assisted
by
conjugated
C=C
bond.
The
follows
a
concomitant
cyclization
rare
triple
functionalization.
totally
regioselective
array
unsymmetrical
alkynes,
taking
leverage
extended
conjugation
or
tertiary
hydroxyl
co-ordination.
mechanism
supported
control
experiments,
KIE
&
labelling
studies
Mass
spectrometry.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(19), P. 13195 - 13203
Published: Sept. 15, 2022
Visible
light
photocatalytic
reactions
of
NH2-enaminones
and
ammonium
thiocyanate
for
chemoselective
α-C-H
thiocyanation
have
been
realized
the
first
time,
providing
a
sustainable
route
synthesis
thiocyanated
NH2-enaminones.
In
addition,
enaminone
products
can
be
flexibly
transformed
into
2-aminothiazoles
2-thiazolinones
via
simple
operation.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(22), P. 5660 - 5666
Published: Jan. 1, 2023
Highly
functionalized
3a,7a-dihydroxy
hexahydro-4
H
-indol-4-ones
were
efficiently
synthesized
via
a
Ru(
iii
)-catalyzed
alkenyl
C(sp
2
)–H
bond
functionalization/[3
+
2]
annulation
reaction
between
readily
available
enaminones
and
iodonium
ylides.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(9), P. 5348 - 5358
Published: April 3, 2023
A
facile
access
to
isocoumarins
has
been
established
via
rhodium(III)-catalyzed
C-H
bond
activation
and
intramolecular
C-C
cascade
annulation
of
enaminones
cyclic
1,3-dicarbonyl
compounds.
The
synthetic
protocol
features
a
wide
range
substrates
with
high
functional
group
tolerance,
mild
reaction
conditions,
the
selective
cleavage
enaminone
bond.
Notably,
compounds
can
in
situ-generate
iodonium
ylide
as
carbene
precursor
prepare
polycyclic
scaffolds
by
reacting
PhI(OAc)2.
application
this
method
useful
precursors
bioactive
skeletons
is
also
exemplified.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
26(5), P. 2705 - 2711
Published: Jan. 1, 2024
A
novel
synthetic
strategy
to
access
strained
heterocycles
is
revealed
through
photocatalysed
annulative
formal
4-
endo-dig
cyclization
of
propargyl
alcohols/amines
with
benzoquinones
under
catalyst/reagent-free
conditions
using
non-hazardous
solvent.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(11), P. 1770 - 1776
Published: March 21, 2023
Abstract
Rh‐catalyzed
C−H
activation
of
arenes
for
oxidative
annulations
with
alkynes
stands
out
as
a
protocol
polycyclic
scaffolds.
This
perspective
drives
us
to
disclose
herein
rhodium
catalyzed
regioselective
triple
annulation
enaminones
hydroxyl‐alkynoates
via
double
functionalization
naphtho‐pyran
Secondary
coordination
OH
in
alkynoate
dictated
the
regioselectivity.
Initial
lactonization
occurred
chemoselectively
on
enamine
part
carbo
rhodation
followed
by
reductive
elimination.
was
scalable
and
has
shown
high
functionality
tolerance.
KIE
studies
were
done
get
insight
mechanism,
some
downstream
transformations
achieved
show
synthetic
potential
method.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(18), P. 2991 - 3019
Published: July 14, 2023
Abstract
Propargylic
alcohols
are
readily
available
bifunctional
(alkyne
and
hydroxyl
groups)
synthons,
which
recognize
as
one
of
the
attractive
synthetic
feedstock
in
organic
transformations.
Especially,
recent
years
employment
these
valuable
molecules
has
frequently
been
observed
literature.
Hence,
present
review
highlights
advancements
application
propargylic
cyclization,
substitution,
addition
reactions.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(31), P. 6602 - 6607
Published: July 30, 2024
Presented
herein
is
a
novel
synthesis
of
indenone-fused
pyran
derivatives
via
the
cascade
reactions
aryl
enaminones
with
cyclopropenones.
The
formation
products
involves
one-pot
procedure
consisting
C–H
bond
and
enamine
functionalization
along
C–C
cleavage
cyclopropenone
1,3-rearrangement
in
situ-formed
allylic
alcohol
moiety
followed
by
intramolecular
O-nucleophilic
addition
Me2NH
elimination.
To
our
knowledge,
this
first
simultaneous
both
indenone
scaffolds
through
concurrent
unsymmetrical
relay
activation
double
C–C/C–O
formation.
Moreover,
usefulness
method
further
showcased
its
suitability
for
large-scale
synthetic
scenarios
diverse
transformations
products.
