Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(18), P. 5206 - 5228
Published: Jan. 1, 2021
Various
alkene
difunctionalization
reactions
involving
nitridization,
diamination,
azidation,
oxyamination,
carboamination,
aminohalogenation,
and
nitration
are
introduced
in
this
review.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(45)
Published: Sept. 12, 2023
Despite
widespread
use
of
the
deuterium
isotope
effect,
selective
labeling
chemical
molecules
remains
a
major
challenge.
Herein,
facile
and
general
electrochemically
driven,
organic
mediator
enabled
deuteration
styrenes
with
oxide
(D2
O)
as
economical
source
was
reported.
Importantly,
this
transformation
could
be
suitable
for
various
electron
rich
mediated
by
triphenylphosphine
(TPP).
The
reaction
proceeded
under
mild
conditions
without
transition-metal
catalysts,
affording
desired
products
in
good
yields
excellent
D-incorporation
(D-inc,
up
to
>99
%).
Mechanistic
investigations
means
experiments
cyclic
voltammetry
tests
provided
sufficient
support
transformation.
Notably,
method
proved
powerful
tool
late-stage
biorelevant
compounds.
Chemical Reviews,
Journal Year:
2023,
Volume and Issue:
123(22), P. 12313 - 12370
Published: Nov. 9, 2023
Late-stage
functionalization
(LSF)
introduces
functional
group
or
structural
modification
at
the
final
stage
of
synthesis
natural
products,
drugs,
and
complex
compounds.
It
is
anticipated
that
late-stage
would
improve
drug
discovery's
effectiveness
efficiency
hasten
creation
various
chemical
libraries.
Consequently,
products
a
productive
technique
to
produce
product
derivatives,
which
significantly
impacts
biology
development.
Carbon-carbon
bonds
make
up
fundamental
framework
organic
molecules.
Compared
with
carbon-carbon
bond
construction,
activation
can
directly
enable
molecular
editing
(deletion,
insertion,
atoms
groups
atoms)
provide
more
efficient
accurate
synthetic
strategy.
However,
selective
unstrained
still
one
most
challenging
projects
in
synthesis.
This
review
encompasses
strategies
employed
recent
years
for
cleavage
by
explicitly
focusing
on
their
applicability
functionalization.
expands
current
discourse
reactions
providing
comprehensive
overview
types
bonds.
includes
C-C(sp),
C-C(sp2),
C-C(sp3)
single
bonds;
double
triple
bonds,
focus
catalysis
transition
metals
organocatalysts.
Additionally,
specific
topics,
such
as
ring-opening
processes
involving
three-,
four-,
five-,
six-membered
rings,
are
discussed,
exemplar
applications
these
techniques
showcased
context
bioactive
molecules
discovery.
aims
shed
light
advancements
field
propose
potential
avenues
future
research
realm
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(5), P. 1297 - 1300
Published: Feb. 8, 2019
The
use
of
additive-free
conditions
is
an
ideal
approach
to
prepare
organoselenium
reagents
from
readily
available
unsaturated
substrates.
Thus,
we
report
the
electro-induced
aminoselenation
and
oxyselenation
styrenes
without
any
acids
or
oxidants
as
additives.
This
transformation
compatible
with
various
functional
groups,
which
leads
vicinal
difunctionalized
compounds.
Our
strategy
improves
potential
this
protocol
for
in
pharmaceutical
industry.
Based
upon
preliminary
mechanism
studies,
propose
two
possible
pathways.
Nature Communications,
Journal Year:
2019,
Volume and Issue:
10(1)
Published: Oct. 31, 2019
Abstract
The
1,2-diamine
motif
is
widely
present
in
natural
products,
pharmaceutical
compounds,
and
catalysts
used
asymmetric
synthesis.
simultaneous
introduction
of
two
amino
groups
across
an
alkene
feedstock
appealing
yet
challenging
approach
for
the
synthesis
1,2-diamines,
primarily
due
to
inhibitory
effect
diamine
products
transition
metal
difficulty
controlling
reaction
diastereoselectivity
regioselectivity.
Herein
we
report
a
scalable
electrocatalytic
1,2-diamination
that
can
be
convert
stable,
easily
available
aryl
alkenes
sulfamides
1,2-diamines
with
excellent
diastereoselectivity.
Monosubstituted
react
regioselective
manner
afford
bearing
different
substituents
on
groups.
combination
organic
redox
catalyst
electricity
not
only
obviates
use
any
oxidizing
reagent,
but
also
ensures
broad
compatibility
variety
electronically
sterically
diverse
substrates.
Journal of the American Chemical Society,
Journal Year:
2020,
Volume and Issue:
142(28), P. 12420 - 12429
Published: July 2, 2020
By
utilizing
an
underexplored
reactivity
mode
of
N-aminopyridinium
ylides,
we
developed
the
visible-light-induced
ortho-selective
aminopyridylation
alkenes
via
radical-mediated
1,3-dipolar
cycloaddition.
The
photocatalyzed
single-electron
oxidation
ylides
generates
corresponding
radical
cations
that
enable
previously
inaccessible
1,3-cycloaddition
with
a
broader
range
alkene
substrates.
resulting
cycloaddition
adducts
rapidly
undergo
subsequent
homolytic
cleavage
N-N
bond,
conferring
substantial
thermodynamic
driving
force
to
yield
various
β-aminoethylpyridines.
Remarkably,
amino
and
pyridyl
groups
can
be
installed
into
both
activated
unactivated
modular
control
ortho-selectivity
1,2-syn-diastereoselectivity
under
metal-free
mild
conditions.
Combined
experimental
computational
studies
are
conducted
clarify
detailed
reaction
mechanism
origins
site
selectivity
diastereoselectivity.
Green Chemistry,
Journal Year:
2019,
Volume and Issue:
21(17), P. 4706 - 4711
Published: Jan. 1, 2019
A
direct
electrochemical
oxidative
cyclization
of
activated
alkynes
with
diselenides
or
disulfides
toward
functionalized
coumarins
and
quinolinones
has
been
developed.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(16), P. 8744 - 8749
Published: Feb. 6, 2021
Abstract
An
efficient
electrochemical
radical
silyl‐oxygenation
of
electron‐deficient
alkenes
is
demonstrated,
which
gives
access
to
a
variety
new
highly
functionalized
silicon‐containing
molecules,
including
β‐silyl‐cyanohydrin
derivatives
in
good
yields
with
excellent
chemo‐
and
regio‐selectivity.
This
silylation
process
conducts
under
mild
conditions
without
the
use
transition
metal
catalyst
or
chemical
oxidant
exhibits
wide
scope
substrate
silanes
high
functional‐group
tolerance.
The
ability
silyl
radicals
using
Si−H
activation
offers
perspectives
for
synthesis
valuable
organosilicon
compounds
sustainable
green
manner.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(8), P. 2536 - 2540
Published: April 4, 2019
The
first
examples
of
electrochemical
trifluoromethylation
and
sulfonylation/semipinacol
rearrangements
allylic
alcohols
were
developed
using
cheap
stable
RSO2Na
(R
=
CF3,
Ph)
as
reagents.
Various
β-trifluoromethyl
sulfonated
ketones
obtained
in
moderate
to
excellent
yields.
This
strategy
provides
a
facile,
direct,
complementary
approach
construct
all-carbon
quaternary
stereocenters.
In
addition,
the
reaction
has
advantages
being
chemical
oxidant-free
metal-free
safe
mild
conditions.
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.
