Chinese Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
44(4), P. 1293 - 1293
Published: Jan. 1, 2024
A
metal-free
catalytic
system
for
the
esterification
reaction
of
N-benzyl-N-t-butoxycarbonyl-amides
with
unsaturated
alcohols
was
reported.With
assistance
amounts
lithium
tert-butoxide,
highly
reactive
N-t-butoxycarbonyl-amides
were
able
to
act
as
electrophiles
and
undergo
reactions
produce
a
series
esters
in
excellent
yields.Furthermore,
this
allowed
relatively
mild
conditions,
making
it
suitable
choice
late-stage
modification
natural
products
drug
molecules.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(5), P. 2794 - 2799
Published: Jan. 25, 2023
A
photoexcited-nitroarene-mediated
anaerobic
C-H
hydroxylation
of
aliphatic
systems
is
reported.
The
success
this
reaction
due
to
the
bifunctional
nature
photoexcited
nitroarene,
which
serves
as
bond
activator
and
oxygen
atom
source.
Compared
previous
methods,
approach
cost-
atom-economical
commercial
availability
sole
mediator
reaction.
Because
conditions
transformation,
a
noteworthy
expansion
in
substrate
scope
can
be
obtained
compared
prior
reports.
Mechanistic
studies
support
that
nitroarenes
engage
successive
hydrogen
transfer
radical
recombination
events
with
hydrocarbons,
leading
N-arylhydroxylamine
ether
intermediates.
Spontaneous
fragmentation
these
intermediates
leads
key
products.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(9), P. 2638 - 2664
Published: Jan. 1, 2024
This
review
describes
the
recent
advances
in
different
reaction
types
and
catalytic
systems
for
construction
of
C–NAr
S–NAr
bonds
by
nitroaromatic
reductive
cross-coupling.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(19), P. 2771 - 2774
Published: Jan. 1, 2023
A
direct
dehydrogenative
amidation
reaction
of
aldehydes
and
amines
under
a
visible
light
mediated
ligand-to-metal
charge
transfer
(LMCT)
process
was
described.
In
this
protocol,
aldehyde
substrates
were
activated
by
photoinduced
hydrogen
atom
abstraction
(HAA),
generating
acyl
chloride
intermediates
followed
nucleophilic
addition
amines.
The
synthetic
method
furnishes
good
functional
group
tolerance
broad
substrate
scope
toward
both
aliphatic
aromatic
components.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(17), P. 4394 - 4399
Published: Jan. 1, 2023
Herein,
we
report
an
effective
C–H
bond
activation-alkylation
strategy
for
2-iodobenzoyl
protected
cyclic
amines
at
the
N
-α-position
through
a
visible-light
mediated
1,5-hydrogen
atom
transfer
(HAT)
process.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(24), P. 4592 - 4597
Published: June 12, 2023
A
fully
catalytic
nickel-photoredox
process
for
the
direct
amidation
of
aldehydes
with
nitroarenes
was
developed.
In
this
system,
and
were
catalytically
activated
by
photocatalytic
cycle
without
addition
an
additional
reductant
or
oxidants,
which
facilitated
Ni-mediated
cross-coupling
C-N
bond
under
mild
conditions.
preliminary
mechanistic
study
indicates
a
reaction
pathway
in
nitrobenzene
is
directly
reduced
to
aniline
as
nitrogen
source.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(14), P. 5735 - 5740
Published: Jan. 1, 2023
An
unprecedented
straightforward
reductive
amidation
of
chloroalkanes
with
nitroarenes
was
readily
accomplished
by
merging
iron
catalysis
visible-light
photoredox
catalysis.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 26, 2025
Direct
C-N
bond
formation
from
nitroarenes
is
a
valuable
synthetic
tool
for
quick
access
to
aniline
derivatives.
Transformation
via
nitroso
intermediates
could
be
useful
due
their
unique
properties,
but
the
generation
of
nitrosoarenes
in
situ
challenging
tendency
various
side
reactions.
Herein
we
report
photoinduced
reductive
[4
+
2]
cycloaddition
nitroarenes.
The
method
begins
with
reduction
give
by
hydrogen
atom
abstraction
(HAA).
generated
undergo
Diels-Alder
(NDA)
reaction.
key
success
use
N-heterocyclic
carbene
(NHC)
borane,
which
promotes
efficient
HAA,
enabling
NDA
reaction
proceed
without
need
transition
metals,
strong
bases,
or
elevated
temperatures.
developed
conditions
allow
high
functional
group
tolerance,
late-stage
functionalization
and
further
derivatization
biologically
active
compounds.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 5, 2025
A
nonconventional
oxidative
denitrogenative
radical
transacetylation
method
for
the
chemoselective
N-acetylation
of
primary
and
secondary
aryl/heteroaryl
amines
using
acetohydrazide
as
a
new
source
acetyl
has
been
discussed.
This
method,
conducted
under
mild,
transition-metal-free
conditions
in
water,
offers
significant
advantages
over
existing
acetylation
strategies,
which
largely
rely
on
harsh
reagents
such
acetic
anhydride,
chloride,
or
enzyme
catalysts.
The
process
utilizes
environmentally
friendly
reagents,
namely,
tert-butyl
hydroperoxide
(TBHP)
ammonium
iodide
(TBAI),
to
generate
radicals
through
cleavage
acetohydrazide,
enabling
efficient
selective
wide
variety
amines,
including
those
bearing
other
sensitive
functional
groups.
Control
experiments
with
scavengers
confirmed
situ
generation
radical,
providing
strong
evidence
proposed
mechanism.
Importantly,
this
protocol
demonstrates
excellent
scalability
successful
application
synthesis
late-stage
functionalization
pharmaceutical
compounds
advanced
drug
intermediates.
not
only
expands
toolkit
amine
but
also
sustainable
scalable
approach
industrial
applications
discovery
development.
