Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(16), P. 6534 - 6538
Published: July 31, 2019
An
efficient
electro-oxidative
C–H/N–H
activation
with
1,3-diynes
has
been
achieved
a
robust
earth-abundant
cobalt
catalyst.
The
electrochemical
C–H
functionalization
was
accomplished
ample
scope
and
remarkable
functional
group
compatibility
in
simple
undivided
cell.
This
protocol
avoids
the
utilization
of
stoichiometric
cost-intensive
chemical
oxidants
activation,
thus
forming
hydrogen
as
only
byproduct.
Chemical Reviews,
Journal Year:
2018,
Volume and Issue:
119(4), P. 2192 - 2452
Published: Nov. 27, 2018
C–H
activation
has
surfaced
as
an
increasingly
powerful
tool
for
molecular
sciences,
with
notable
applications
to
material
crop
protection,
drug
discovery,
and
pharmaceutical
industries,
among
others.
Despite
major
advances,
the
vast
majority
of
these
functionalizations
required
precious
4d
or
5d
transition
metal
catalysts.
Given
cost-effective
sustainable
nature
earth-abundant
first
row
metals,
development
less
toxic,
inexpensive
3d
catalysts
gained
considerable
recent
momentum
a
significantly
more
environmentally-benign
economically-attractive
alternative.
Herein,
we
provide
comprehensive
overview
on
until
summer
2018.
Chemical Reviews,
Journal Year:
2020,
Volume and Issue:
120(3), P. 1788 - 1887
Published: Jan. 6, 2020
During
the
past
decades,
synthetic
organic
chemistry
discovered
that
directing
group
assisted
C–H
activation
is
a
key
tool
for
expedient
and
siteselective
construction
of
C–C
bonds.
Among
various
strategies,
bidentate
groups
are
now
recognized
as
one
most
efficient
devices
selective
functionalization
certain
positions
due
to
fact
its
metal
center
permits
fine,
tunable,
reversible
coordination.
The
family
permit
types
assistance
be
achieved,
such
N,N-dentate,
N,O-dentate,
N,S-dentate
auxiliaries,
which
categorized
based
on
coordination
site.
In
this
review,
we
broadly
discuss
bond
reactions
formation
bonds
with
aid
groups.
Chemical Reviews,
Journal Year:
2019,
Volume and Issue:
119(12), P. 6769 - 6787
Published: May 10, 2019
Photo-/electrochemical
catalyzed
oxidative
R1-H/R2-H
cross-coupling
with
hydrogen
evolution
has
become
an
increasingly
important
issue
for
molecular
synthesis.
The
dream
of
construction
C-C/C-X
bonds
from
readily
available
C-H/X-H
release
H2
can
be
facilely
achieved
without
external
chemical
oxidants,
providing
a
greener
model
bond
formation.
Given
the
great
influence
these
reactions
in
organic
chemistry,
we
give
summary
state
art
via
photo/electrochemistry,
and
hope
this
review
will
stimulate
development
synthetic
strategy
near
future.
Accounts of Chemical Research,
Journal Year:
2019,
Volume and Issue:
53(1), P. 84 - 104
Published: Dec. 19, 2019
To
improve
the
efficacy
of
molecular
syntheses,
researchers
wish
to
capitalize
upon
selective
modification
otherwise
inert
C-H
bonds.
The
past
two
decades
have
witnessed
considerable
advances
in
coordination
chemistry
that
set
stage
for
transformative
tools
functionalizations.
Particularly,
oxidative
C-H/C-H
and
C-H/Het-H
transformations
gained
major
attention
because
they
avoid
all
elements
substrate
prefunctionalization.
Despite
advances,
activations
been
dominated
by
precious
transition
metal
catalysts
based
on
palladium,
ruthenium,
iridium,
rhodium,
thus
compromising
sustainable
nature
overall
activation
approach.
same
holds
true
predominant
use
stoichiometric
chemical
oxidants
regeneration
active
catalyst,
prominently
featuring
hypervalent
iodine(III),
copper(II),
silver(I)
oxidants.
Thereby,
quantities
undesired
byproducts
are
generated,
which
preventive
applications
scale.
In
contrast,
elegant
merger
homogeneous
metal-catalyzed
with
electrosynthesis
bears
unique
power
achieve
outstanding
levels
oxidant
resource
economy.
Thus,
contrast
classical
electrosyntheses
control,
metalla-electrocatalysis
huge
largely
untapped
potential
unmet
site
selectivities
means
catalyst
control.
While
indirect
electrolysis
using
palladium
complexes
has
realized,
less
toxic
expensive
base
feature
distinct
beneficial
assets
toward
this
Account,
I
summarize
emergence
electrocatalyzed
earth-abundant
3d
metals
beyond,
a
topical
focus
contributions
from
our
laboratories
through
November
2019.
cobalt
electrocatalysis
was
identified
as
particularly
powerful
platform
wealth
transformations,
including
oxygenations
nitrogenations
well
alkynes,
alkenes,
allenes,
isocyanides,
carbon
monoxide,
among
others.
As
complementary
tools,
nickel,
copper,
very
recently
iron
devised
metalla-electrocatalyzed
activations.
Key
success
were
detailed
mechanistic
insights,
oxidation-induced
reductive
elimination
scenarios.
Likewise,
development
methods
make
weak
O-coordination
benefited
crucial
insights
into
catalyst's
modes
action
experiment,
operando
spectroscopy,
computation.
Overall,
thereby
syntheses
These
electrooxidative
frequently
characterized
improved
chemoselectivities.
Hence,
ability
dial
redox
at
minimum
level
required
desired
transformation
renders
an
ideal
functionalization
structurally
complex
molecules
sensitive
functional
groups.
This
strategy
was,
inter
alia,
successfully
applied
scale-up
continuous
flow
step-economical
assembly
polycyclic
aromatic
hydrocarbons.
Chemical Reviews,
Journal Year:
2021,
Volume and Issue:
122(3), P. 3180 - 3218
Published: Nov. 19, 2021
Synthetic
organic
electrosynthesis
has
grown
in
the
past
few
decades
by
achieving
many
valuable
transformations
for
synthetic
chemists.
Although
electrocatalysis
been
popular
improving
selectivity
and
efficiency
a
wide
variety
of
energy-related
applications,
last
two
decades,
there
much
interest
to
develop
conceptually
novel
transformations,
selective
functionalization,
sustainable
reactions.
This
review
discusses
recent
advances
combination
electrochemistry
homogeneous
transition-metal
catalysis
synthesis.
The
enabling
mechanistic
studies
are
presented
alongside
advantages
as
well
future
directions
address
challenges
metal-catalyzed
electrosynthesis.
Chemical Reviews,
Journal Year:
2023,
Volume and Issue:
123(19), P. 11269 - 11335
Published: Sept. 26, 2023
Late-stage
functionalization
(LSF)
constitutes
a
powerful
strategy
for
the
assembly
or
diversification
of
novel
molecular
entities
with
improved
physicochemical
biological
activities.
LSF
can
thus
greatly
accelerate
development
medicinally
relevant
compounds,
crop
protecting
agents,
and
functional
materials.
Electrochemical
synthesis
has
emerged
as
an
environmentally
friendly
platform
transformation
organic
compounds.
Over
past
decade,
electrochemical
late-stage
(eLSF)
gained
major
momentum,
which
is
summarized
herein
up
to
February
2023.
Angewandte Chemie International Edition,
Journal Year:
2018,
Volume and Issue:
57(43), P. 14179 - 14183
Published: Sept. 10, 2018
Iridium-catalyzed
electrochemical
C-H
activation
was
accomplished
within
a
cooperative
catalysis
manifold,
setting
the
stage
for
electrooxidative
alkenylations
through
weak
O-coordination.
The
iridium-electrocatalyzed
featured
high
functional-group
tolerance
assistance
of
metal-free
redox
mediator
indirect
electrolysis.
Detailed
mechanistic
insights
provided
strong
support
an
organometallic
cleavage
and
synergistic
iridium(III/I)/redox
catalyst
regime,
enabling
use
sustainable
electricity
as
terminal
oxidant
with
improved
selectivity
features.
