Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 3, 2025
Selective
functionalization
of
remote
C-H
bonds
via
metal/hydride
shift
and
cross-coupling
represents
a
powerful
strategy
in
modern
synthetic
chemistry.
Herein,
we
report
highly
efficient
aryl-to-vinyl
1,4-nickel
migration
coupled
with
reductive
for
the
stereoselective
synthesis
conjugated
dienes.
This
tandem
process
proceeds
under
mild
conditions,
accommodates
wide
range
substrates,
achieves
excellent
regioselectivity
Z/E
stereoselectivity,
offering
valuable
method
constructing
multisubstituted
Chemical Reviews,
Journal Year:
2022,
Volume and Issue:
122(24), P. 17479 - 17646
Published: Oct. 14, 2022
Alkenes
and
their
derivatives
are
featured
widely
in
a
variety
of
natural
products,
pharmaceuticals,
advanced
materials.
Significant
efforts
have
been
made
toward
the
development
new
practical
methods
to
access
this
important
class
compounds
by
selectively
activating
alkenyl
C(sp2)–H
bonds
recent
years.
In
comprehensive
review,
we
describe
state-of-the-art
strategies
for
direct
functionalization
sp2
C–H
C–F
until
June
2022.
Moreover,
metal-free,
photoredox,
electrochemical
also
covered.
For
clarity,
review
has
divided
into
two
parts;
first
part
focuses
on
currently
available
using
different
alkene
as
starting
materials,
second
describes
bond
easily
accessible
gem-difluoroalkenes
material.
This
includes
scope,
limitations,
mechanistic
studies,
stereoselective
control
(using
directing
groups
well
metal-migration
strategies),
applications
complex
molecule
synthesis
where
appropriate.
Overall,
aims
document
considerable
advancements,
current
status,
emerging
work
critically
summarizing
contributions
researchers
working
fascinating
area
is
expected
stimulate
novel,
innovative,
broadly
applicable
functionalizations
coming
Chemical Society Reviews,
Journal Year:
2021,
Volume and Issue:
50(5), P. 3013 - 3093
Published: Jan. 1, 2021
This
review
provides
an
overview
of
the
fundamental
concepts
and
recent
developments
in
a
wide
range
enantioselective
transformations
involving
oxa-
azabicyclic
alkenes.
Nature Communications,
Journal Year:
2023,
Volume and Issue:
14(1)
Published: Feb. 25, 2023
Abstract
Asymmetric
ring-opening
of
7-oxabenzonorbornadienes
is
achieved
via
Co-catalyzed
indole
C–H
functionalization.
The
utilization
chiral
Co-catalyst
consisting
a
binaphthyl-derived
trisubstituted
cyclopentadienyl
ligand
resulted
in
high
yields
(up
to
99%)
and
excellent
enantioselectivity
(>99%
ee)
for
the
target
products
with
tolerance
diverse
functional
groups.
Opposite
diastereoselectivities
are
obtained
or
Cp*CoI
2
CO.
Combined
experimental
computational
studies
suggest
β
-oxygen
elimination
being
selectivity-determining
step
reaction.
Meanwhile,
reactions
7-azabenzonorbornadiene
could
also
be
executed
diastereodivergent
manner.
Organic Chemistry Frontiers,
Journal Year:
2020,
Volume and Issue:
7(16), P. 2284 - 2290
Published: Jan. 1, 2020
An
efficient
synthesis
of
pyrazolone
fused
benzodiazepines
through
an
unprecedented
regioselective
[4
+
3]
annulation
1-phenylpyrazolidinones
with
propargyl
alcohols
via
Rh(iii)-catalyzed
redox-neutral
C–H/N–H/C–O
bond
activation
is
presented.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(3), P. 2328 - 2338
Published: Jan. 12, 2021
A
Rh(III)-catalyzed
dehydrogenative
annulation
and
spirocyclization
of
2-arylindoles
2-(1H-pyrazol-1-yl)-1H-indole
with
maleimides
is
described.
The
cascade
protocol
provided
highly
functionalized
benzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-diones
spiro[isoindolo[2,1-a]indole-6,3′-pyrrolidine]-2′,5′-diones
in
good
to
excellent.
developed
reaction
methodology
exhibited
broad
substrate
scope
functional
group
tolerance
operationally
simple
scalable.
Photophysical
properties
the
annulated
products
were
investigated.
product
showed
high
absorption
emission
values
a
large
red-shift
as
compared
that
2-phenylindole.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(24), P. 4837 - 4845
Published: Jan. 1, 2022
Transition-metal-catalyzed
directed
C-H
alkenylation
with
maleimides
has
attracted
much
attention
in
recent
years,
as
maleimide
core
moieties
are
present
various
natural
products
and
pharmaceuticals.
In
addition,
these
derivatives
can
be
readily
modified
into
biologically
important
compounds
including
succinimides,
pyrrolidines
γ-lactams.
The
efficient
chelation-assisted
inert
bond
activation
strategy
provides
straightforward
access
to
a
wide
array
of
structurally
diverse
molecules
containing
units.
This
review
describes
the
major
progress
mechanistic
investigations
on
Heck-type
reaction/cyclization
organic
until
early
2022.
European Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
2021(43), P. 5862 - 5879
Published: Oct. 20, 2021
Abstract
Maleimides
and
succinimides
are
all
vital
scaffolds
in
biological
fields
various
natural
products.
Maleimide
derivatives
have
been
extensively
used
as
coupling
partners
for
organic
transformations,
affording
a
broad
array
of
important
molecular
architectures
including
succinimides.
In
the
past
decade,
variety
efficient
chelation‐assisted
strategies
employed
selective
addition
C−H
bonds
to
maleimides
giving
succinimides,
which
also
highly
building
blocks
synthesis.
This
Review
provides
an
overview
research
progress
relating
participated
transition‐metal‐catalyzed
group‐directed
alkylation
from
2012
2021.
Significant
advances
this
field
were
highlighted,
diverse
transition
metal
catalysts,
substrates
contained
different
directing
groups,
reaction
mechanisms
well
synthetic
applications
systematically
discussed.
addition,
limitations
intractable
issues
need
be
solved
future
pointed
out.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(17), P. 6760 - 6764
Published: Aug. 14, 2020
A
free
amine-directed
ruthenium(II)-catalyzed
hydroarylation
and
concomitant
regioselective
transamidation
cascade
between
2-aminobiphenyls
diversely
substituted
maleimides
is
reported,
furnishing
biologically
relevant
dibenzo[b,d]azepinone
scaffolds
in
high
yields.
The
protocol
accommodates
a
range
of
functional
groups
showcases
synthesis
dibenzoazepinones
bearing
amino
acid
side
chains
through
substrate
design.
Chemical Communications,
Journal Year:
2021,
Volume and Issue:
57(70), P. 8699 - 8725
Published: Jan. 1, 2021
Metal
catalyzed
C–H
functionalization
is
a
convenient
and
powerful
strategy
to
construct
various
N,O-heterocycles.
This
review
highlights
the
recent
breakthroughs
in
synthesis
of
N,O-heterocycles
via
directed
sp
2
functionalization.
Beilstein Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
17, P. 2209 - 2259
Published: Aug. 31, 2021
Catalytic
C‒H
functionalization
has
become
a
powerful
strategy
in
organic
synthesis
due
to
the
improved
atom-,
step-
and
resource
economy
comparison
with
cross-coupling
or
classical
functional
group
transformations.
Despite
significant
advances
metal-catalyzed
activations,
recent
developments
field
of
metallaphotoredox
catalysis
enabled
functionalizations
unique
reaction
pathways
under
mild
conditions.
Given
relative
earth-abundance
cost-effective
nature,
nickel
catalysts
for
photoredox
have
received
attention.
In
this
review,
we
highlight
nickel-catalyzed
reactions
range
applications
until
summer
2021.