The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(6), P. 4168 - 4182
Published: Feb. 25, 2022
Photoredox
neutral
decarboxylative
hydroxyalkylations
of
heteroarenes
with
α-keto
acids
under
mild
conditions
are
described.
Stable
and
readily
available
were
employed
as
hydroxyalkylating
reagents
only
CO2
released
the
byproduct.
A
range
aromatic
aliphatic
successfully
converted
into
hydroxyalkylated
products
various
heteroarenes.
This
transformation
proceeded
through
a
decarboxylation/Minisci
addition/SCS
sequence,
generating
variety
valuable
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(8), P. 2976 - 2980
Published: March 29, 2021
A
general
and
metal-free
visible-light-induced
decarboxylative
arylation
procedure
at
room
temperature
was
described
for
the
construction
of
acylated
heterocyclic
derivatives,
such
as
benzimidazo/indolo[2,1-a]isoquinolin-6(5H)-ones,
aroylazaspiro[4.5]trienones,
thioflavones,
so
on.
This
practical
conducted
by
using
2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile
(4CzIPN)
a
photocatalyst
under
mild
conditions,
which
avoided
use
an
additional
base,
traditional
heating,
metal
reagents.
ACS Sustainable Chemistry & Engineering,
Journal Year:
2021,
Volume and Issue:
9(12), P. 4296 - 4323
Published: March 16, 2021
Pollutants
from
industry
and
chemical
laboratories
have
harmful
effects
on
human
health
the
environment.
Concerns
about
this
problem
led
to
development
of
more
versatile
sustainable
protocols
based
principles
green
chemistry.
One
these
innovative
approaches
is
carry
out
reactions
under
visible-light
sources
without
photocatalysts.
This
benign,
simple,
cost-effective
method,
inspired
by
nature,
could
be
a
suitable
alternative
some
classical
methods,
change
harsh
reaction
conditions
into
milder
ones.
In
Perspective,
we
outlined
results
catalyst-free
organic
further
encourage
researchers
in
promising
field.
The
proposed
mechanisms
generation
an
electron
donor–acceptor
complex
(EDA)
single-electron
transfer
(SET)
pathway
were
discussed.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(11), P. 2678 - 2722
Published: March 31, 2021
Abstract
Carboxylic
acids
are
among
the
most
used
feedstock
chemicals
due
to
their
great
structural
diversity
and
easy
handling.
The
use
of
carboxylic
derivatives
in
decarboxylative
couplings
has
proven
be
a
valuable
tool
for
construction
C−C
C‐heteroatom
bonds.
This
synthetic
strategy
provides
complementary
bond
disconnection
traditional
cross‐coupling
methods.
In
this
review,
we
provide
comprehensive
overview
decarboxylation‐initiated
intermolecular
formation,
outlining
several
main
mechanistic
concepts
combined
with
early
examples
highlighting
achievements
made
past
decade
until
January
2021.
these
reactions,
undergo
initial
decarboxylation
then
react
other
heteroatom
electrophiles
nucleophiles,
thus
replacing
carboxylate
group
prevalent
functionality.
magnified
image
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(2), P. 498 - 502
Published: Jan. 9, 2024
The
convenient
and
precise
preparation
of
N,N′-diarylhydrazides,
especially
from
readily
available
raw
materials,
remains
highly
challenging.
Here,
a
photoredox
catalytic
phosphine-mediated
deoxygenative
hydroacylation
azobenzenes
with
abundant
carboxylic
acids
has
been
developed.
With
Ir[dF(CF3)ppy]2(dtbbpy)PF6
as
the
photocatalyst,
reactions
proceeded
smoothly
in
presence
PPh3
under
visible
light
irradiation,
delivering
various
N,N′-diarylhydrazides
up
to
92%
yields.
Mechanistic
studies
revealed
that
reaction
proceeds
via
catalysis
phosphoranyl-radical-mediated
C–O
bond
cleavage
acids.
Chemical Society Reviews,
Journal Year:
2024,
Volume and Issue:
53(10), P. 4926 - 4975
Published: Jan. 1, 2024
In
search
for
the
perfect
wave(length).
This
review
is
dedicated
to
recent
efforts
in
development
of
visible
light
driven
photochemical
strategies
occurring
coloured
organic
compounds.
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(11), P. 1230 - 1236
Published: Feb. 5, 2024
Comprehensive
Summary
A
visible‐light‐enabled,
photocatalyst‐free
hydroacylation
reaction
of
azodicarboxylic
acid
derivatives
was
described.
This
radical
conjugate
addition
(RCA)
protocol
relied
on
the
dual
role
4‐acyl‐1,4‐dihydropyridine
(acyl‐DHP)
reagents
that
besides
being
as
reservoirs,
they
also
enabled
conversion
adducts
to
anion
intermediates
via
reduction.
Under
“catalyst‐oxidant‐additive
free”
conditions,
a
wide
range
structurally
different
acyl
hydrazide
products
were
readily
obtained
in
56%—99%
yields.
The
utility
this
transformation
further
demonstrated
by
scale‐up
synthesis
and
downstream
derivatization.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(10), P. 2039 - 2044
Published: March 4, 2024
We
report
the
synthesis
of
acyl
hydrazides
from
acylsilanes
in
presence
visible
light
without
aid
additives
or
transition
metals.
Acylsilanes
underwent
[1,2]-Brook
rearrangement
to
generate
nucleophilic
siloxycarbenes
which
on
further
addition
N═N
azodicarboxylates
produced
hydrazides.
Control
experiments
indicate
that
reaction
proceeds
through
singlet
carbene
intermediate.
Transformation
hydrazide
functionality
other
functional
groups
was
demonstrated,
including
drug
candidate
Moclobemide.
Green Chemistry,
Journal Year:
2021,
Volume and Issue:
23(16), P. 5806 - 5811
Published: Jan. 1, 2021
Direct
synthesis
of
1,2,4-triazolidines
have
been
readily
achieved
by
the
visible-light-promoted
reaction
N
-aryl
glycines
and
azobenzenes
under
mild
conditions.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(7), P. 1530 - 1535
Published: Feb. 14, 2022
A
visible-light-promoted
aerobic
oxyphosphorylation
of
α-diazoesters
and
H-phosphine
oxides
has
been
developed.
Using
air
as
the
oxygen
source,
reaction
proceeded
smoothly
at
room
temperature
under
blue-light
irradiation.
The
α-diazoesters,
molecular
oxygen,
are
conveniently
incorporated
into
a
C-O-P(O)
unit
in
one
step.
preliminary
mechanistic
studies
indicated
that
light-triggered
radical
process
is
involved.
developed
strategy
shows
unrevealed
reactivity
diazo
compounds
with
potential
value
synthetic
applications.
