Chemistry - A European Journal,
Journal Year:
2020,
Volume and Issue:
26(44), P. 9688 - 9709
Published: April 1, 2020
Selective
C-H
bond
functionalization
catalyzed
by
metal
complexes
have
completely
revolutionized
the
way
in
which
chemical
synthesis
is
conceived
nowadays.
Typically,
reactivity
of
a
transition
catalyst
key
to
control
site-,
regio-
and/or
stereo-selectivity
functionalization.
Of
particular
interests
are
molecules
that
contain
multiple
bonds
prone
undergo
activations
with
very
similar
dissociation
energies
at
different
positions.
This
case
benzanilides,
relevant
motifs
found
many
useful
fine
chemicals,
two
sites
present
chemically
aromatic
fragments.
In
last
years,
it
has
been
depending
on
and
reaction
conditions,
amide
motif
might
behave
as
directing
group
towards
metal-catalyzed
activation
benzamide
site
or
anilide
site.
The
impact
consequences
such
subtle
site-selectivity
herein
reviewed
important
applications
carbon-carbon
carbon-heteroatom
forming
processes.
mechanisms
unraveling
these
unique
transformations
discussed
order
provide
better
understanding
for
future
developments
field
site-selective
catalysts.
Organic Chemistry Frontiers,
Journal Year:
2020,
Volume and Issue:
7(12), P. 1527 - 1569
Published: Jan. 1, 2020
Heterocyclic
alkenes
and
their
derivatives
are
an
important
class
of
reactive
feedstock
valuable
synthons.
This
review
highlights
the
transition-metal-catalyzed
coupling
heterocyclic
alkenesviaa
C–H
functionalization
strategy.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(43), P. 23187 - 23192
Published: Aug. 26, 2021
Abstract
An
unprecedented
enantioselective
synthesis
of
spiro‐γ‐lactams
via
a
sequential
C−H
olefination/asymmetric
[4+1]
spirocyclization
under
simple
Co
II
/chiral
spiro
phosphoric
acid
(SPA)
binary
system
is
reported.
A
range
biologically
important
are
obtained
with
high
levels
enantioselectivity
(up
to
98
%
ee
).
The
concise,
asymmetric
an
aldose
reductase
inhibitor
was
successfully
achieved.
Notably,
contrast
previous
reports
that
relied
on
the
use
cyclopentadienyl
or
its
derivatives
(achiral
Cp*,
Cp
tBu
,
chiral
x
)
ligated
III
complexes
requiring
tedious
steps
prepare,
cheap
and
commercially
available
cobalt(II)
acetate
tetrahydrate
used
as
efficient
precatalyst.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(12), P. 4525 - 4530
Published: June 10, 2019
A
weakly
coordinating
carboxylate
directing
group
assisted
C–H
activation
with
maleimides
leading
to
novel
and
switchable
decarboxylative
Heck-type
[4
+
1]
annulation
products
catalyzed
by
Rh(III)
has
been
reported.
In
these
reactions,
solvents
play
a
vital
role
in
switching
the
selectivity.
An
aprotic
solvent,
THF,
leads
product
while
protic
TFE,
results
product.
The
methodology
shows
high
functional
tolerance.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(19), P. 8138 - 8143
Published: Sept. 23, 2019
Herein,
we
disclosed
the
first
report
on
selective
C(4)–H
functionalization
of
3-acetylindole
derivatives
using
first-row
transition
metal
cobalt
where
an
acetyl
group
is
acting
as
a
weakly
coordinating
directing
group.
Selective
has
been
achieved
diverse
Michael
acceptors
(acrylate
and
maleimide)
simply
by
switching
additive
from
copper
acetate
to
silver
carbonate.
Further
formation
cobaltacycle
intermediate
was
also
detected
through
HRMS
for
mechanistic
insight.
Chemistry - An Asian Journal,
Journal Year:
2020,
Volume and Issue:
15(14), P. 2092 - 2109
Published: June 5, 2020
2-Pyridone
is
a
ubiquitous
motif
in
natural
products,
drug
molecules,
ligands
catalysis
and
organic
materials.
There
necessity
of
direct
step-economic
methods
for
the
construction
2-pyridone
based
molecules.
Strategically,
primary
developments
have
led
to
C3-functionalizations
due
inherent
reactivity
this
center.
Despite
this,
many
elegant
transition
metal-catalysed
been
established
introduce
versatile
functional
groups
at
C4,
C5
C6-position
via
C-H
bond
functionalizations.
This
minireview
focuses
on
categorized
introduction
different
scaffolds
beyond
C3-selectivity
discusses
substrate
scope,
limitations
plausible
mechanistic
details.
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.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(3), P. 2784 - 2795
Published: Jan. 14, 2021
A
Ru(II)-catalyzed
facile
and
controllable
protocol
for
C–H
alkylation
spirocyclization
of
2-arylquinoxalines
with
maleimides
has
been
achieved
under
ambient
air
in
high
yields.
Sequential
ortho-C–H
activation
C-annulation
results
the
formation
diverse
polyheterocycles
containing
spiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolidine]-2′,5′-diones,
which
are
potent
interest
medicinal
chemistry.
Mechanistic
investigations
suggest
a
reversible
cleavage
bond
turnover-limiting
step.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(16), P. 2612 - 2633
Published: Jan. 1, 2022
Advancements
in
the
palladium-catalyzed
functionalization
of
diastereotopic
or
prochiral
C(sp
3
)–H
bonds
generating
stereogenic
centers
and
stereo-arrays
aliphatic
compounds
have
been
highlighted.
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.