Chemical Society Reviews,
Journal Year:
2022,
Volume and Issue:
51(16), P. 7206 - 7237
Published: Jan. 1, 2022
This
review
covers
the
recent
progress
in
electro-/photo-catalytic
alkene-derived
radical
cation
chemistry
for
organic
synthesis,
including
synthetic
strategies,
plausible
mechanisms
and
further
research
outlook.
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(34), P. 15871 - 15878
Published: Aug. 19, 2022
The
concurrent
installation
of
C-C
and
C-N
bonds
across
alkene
frameworks
represents
a
powerful
tool
to
prepare
motifs
that
are
ubiquitous
in
pharmaceuticals
bioactive
compounds.
To
construct
such
prevalent
bonds,
most
difunctionalization
methods
demand
the
use
precious
metals
or
activated
alkenes.
We
report
metal-free,
photochemically
mediated
imino-alkylation
electronically
diverse
alkenes
install
both
alkyl
iminyl
groups
highly
efficient
manner.
exceptionally
mild
reaction
conditions,
broad
substrate
scope,
excellent
functional
group
tolerance,
facile
one-pot
protocol
highlight
utility
this
method
privileged
from
readily
available
acid
feedstocks.
One
key
striking
feature
transformation
is
an
electrophilic
trifluoromethyl
radical
equally
with
electron-deficient
electron-rich
Additionally,
dispersion-corrected
density
theory
(DFT)
empirical
investigations
provide
detailed
mechanistic
insight
into
reaction.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(5), P. 1322 - 1345
Published: Jan. 1, 2023
Functionalization
of
alkenes/alkynes
is
a
highly
effective
route
to
achieve
molecular
complexity.
This
review
summarizes
recent
progresses
on
the
1,2-difunctionalization/hydrofunctionalization
unactivated
with
C−S
bond
formation.
Green Chemistry,
Journal Year:
2021,
Volume and Issue:
23(17), P. 6632 - 6638
Published: Jan. 1, 2021
This
study
demonstrates
a
metal-free
cross-dehydrogenative
coupling
for
direct
para
-C–H
heteroarylation
of
anilines
with
quinoxalinones
using
air
as
the
sole
oxidant
and
H
2
O/DMSO
solvent.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(8), P. 2256 - 2279
Published: Jan. 1, 2022
In
this
review
article,
we
summarized
recent
advances
in
the
transition
metal-catalyzed
heteroannulative
difunctionalization
of
alkenes
via
direct
C–H
activation
to
access
heterocyclic
frameworks.
Synthesis,
Journal Year:
2022,
Volume and Issue:
54(15), P. 3432 - 3472
Published: April 13, 2022
Abstract
Nitro
compounds
are
vital
raw
chemicals
that
widely
used
in
academic
laboratories
and
industries
for
the
preparation
of
various
drugs,
agrochemicals,
materials.
Thus,
nitrating
reactions
great
importance
chemists
even
taught
schools
as
one
fundamental
transformations
organic
synthesis.
Since
discovery
first
19th
century,
progress
this
field
has
been
constant.
Yet,
many
years
classical
electrophilic
nitration
approach
using
a
mixture
strong
mineral
acids
dominated
field.
However,
recent
decades,
attention
researchers
focused
on
new
reactivity
reagents
can
provide
access
to
nitro
practical
straightforward
way
under
mild
reaction
conditions.
Organic
have
played
special
role
since
they
enhanced
reactivity.
They
also
allow
be
carried
out
an
ecofriendly
sustainable
manner.
This
review
examines
development
application
reagents.
1
Introduction
2
Nitrating
Reagents
2.1
Alkyl
Nitrites
2.2
Nitroalkanes
2.3
Nitrates
2.4
N-Nitroamides
2.5
N-Nitropyrazole
2.6
N-Nitropyridinium
Salts
3
Generated
In
Situ
3.1
Acyl
3.2
Trimethylsilyl
Nitrate
3.3
Onium
4
Nitronium
5
5.1
Ammonium
5.2
Heteroarylium
5.3
Other
5.4
6
Conclusion
Outlook
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(15), P. 8299 - 8307
Published: April 6, 2023
Modular
strategies
to
rapidly
increase
molecular
complexity
have
proven
immensely
synthetically
valuable.
In
principle,
transformation
of
an
alkene
into
a
dielectrophile
presents
opportunity
deliver
two
unique
nucleophiles
across
alkene.
Unfortunately,
the
selectivity
profiles
known
dielectrophiles
largely
precluded
this
deceptively
simple
synthetic
approach.
Herein,
we
demonstrate
that
dicationic
adducts
generated
through
electrolysis
alkenes
and
thianthrene
possess
profile
relative
more
conventional
dielectrophiles.
Specifically,
these
species
undergo
single
perfectly
regioselective
substitution
reaction
with
phthalimide
salts.
This
observation
unlocks
appealing
new
platform
for
aminofunctionalization
reactions.
As
illustrative
example,
implement
reactivity
paradigm
address
longstanding
challenge:
diamination
distinct
nitrogen
nucleophiles.
Studies
mechanism
process
reveal
key
alkenyl
thianthrenium
salt
intermediate
controls
exquisite
regioselectivity
highlight
importance
proton
sources
in
controlling
sulfonium
electrophiles.
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(9), P. 2447 - 2454
Published: Jan. 1, 2023
Intermolecular
carboamination
of
olefins
offers
a
powerful
platform
for
the
rapid
construction
structurally
complex
amines
from
abundant
feedstocks.
However,
these
reactions
often
require
transition-metal
catalysis,
and
are
mainly
limited
to
1,2-carboamination.
Herein,
we
report
novel
radical
relay
1,4-carboimination
across
two
distinct
with
alkyl
carboxylic
acid-derived
bifunctional
oxime
esters
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
11(2), P. 597 - 630
Published: Nov. 23, 2023
This
review
highlights
the
recent
progress
in
electrochemical
difunctionalization
of
alkenes
and
alkynes
involving
C–S/Se
bond
formation
to
access
organochalcogen
frameworks.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 2939 - 2944
Published: April 11, 2024
A
selective
three-component
1,2-sulfonyl
etherification
of
aryl
1,3-dienes
enabled
by
copper
catalysis
to
afford
biologically
interesting
alkenyl
1,2-sulfone
ether
derivatives
through
C–S
and
C–O
bond
formation
is
described.
The
protocol
proceeds
with
the
sulfonyl
chloride
alcohols
under
simple,
mild,
base-free
conditions,
providing
a
straightforward
route
sulfonylated
allyl
compounds
broad
functional
group
tolerance
excellent
chemo-
regioselectivity.
Mechanistic
studies
indicate
that
alkene
difunctionalization
includes
key
copper-mediated
single-electron
transfer
process.
