The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14649 - 14658
Published: Oct. 10, 2023
A
metal-free
and
selective
oxidative
methyl
C-H
functionalization
of
BHT
with
aniline
compounds
has
been
developed.
This
innovative
method
enables
the
facile
efficient
synthesis
a
diverse
array
BHT-functionalized
N-containing
skeletons,
including
arylamines,
benzoxazoles,
benzothiazoles,
benzimidazoles,
quinazolines,
quinazolinones,
all
which
are
challenging
to
access.
The
control
experiment
involving
TEMP18O
suggests
that
radical
adduct
TEMPO
benzyl
may
serve
as
an
intermediate.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(10), P. 6730 - 6741
Published: May 12, 2022
Multicomponent
synthesis
of
biologically
relevant
S-benzyl
dithiocarbamates
from
para-quinone
methides,
amines,
and
carbon
disulfide
are
described
under
catalyst
additive-free
conditions.
The
reactions
proceeded
at
room
temperature
in
a
short
span
time
with
excellent
yields.
One
the
synthesized
compounds,
3e
showed
considerable
acetylcholinesterase
(AChE)
inhibitory
(51.70
+
5.63%
20
μm)
antioxidant
(63.52
±
1.15
activities.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(5), P. 3033 - 3048
Published: Feb. 19, 2024
A
novel
and
efficient
protocol
for
the
synthesis
of
diarylallyl-functionalized
phosphonates,
phosphinates,
phosphine
oxides
through
zinc-catalyzed
dehydroxylative
phosphorylation
allylic
alcohols
with
P(III)-nucleophiles
via
a
Michaelis–Arbuzov-type
rearrangement
is
reported.
broad
range
(P(OR)3,
ArP(OR)2,
Ar2P(OR))
are
well
tolerated
in
this
reaction,
expected
products
could
be
synthesized
good
to
excellent
yields
under
optimal
reaction
conditions.
The
can
easily
scaled
up
at
gram-synthesis
level.
Furthermore,
step-by-step
control
experiments,
kinetic
study
31P
NMR
tracking
we
acquired
insights
into
proposed
possible
mechanism
transformation.
International Journal of Molecular Sciences,
Journal Year:
2022,
Volume and Issue:
23(6), P. 3395 - 3395
Published: March 21, 2022
Compounds
bearing
the
phosphorus–carbon
(P–C)
bond
have
important
pharmacological,
biochemical,
and
toxicological
properties.
Historically,
most
notable
reaction
for
formation
of
P–C
is
Michaelis–Arbuzov
reaction,
first
described
in
1898.
The
classical
entails
a
between
an
alkyl
halide
trialkyl
phosphite
to
yield
dialkylalkylphosphonate.
Nonetheless,
deviations
from
mechanisms
new
modifications
appeared
that
allowed
expansion
library
reactants
consequently
chemical
space
yielded
products.
These
involve
use
Lewis
acid
catalysts,
green
methods,
ultrasound,
microwave,
photochemically-assisted
reactions,
aryne-based
etc.
Here,
detailed
presentation
its
developments
applications
synthesis
biomedically
agents
provided.
Certain
examples
such
include
development
alkylphosphonofluoridates
as
serine
hydrolase
inhibitors
activity-based
probes,
containing
antiviral
anticancer
agents.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(56), P. 7196 - 7199
Published: Jan. 1, 2024
A
silver-catalyzed
P-centered
anion-initiated
cascade
reaction
of
functionalized
arylisocyanides
with
H-phosphorus
oxides
was
established
for
the
expeditious
synthesis
various
2-phosphinoyl-indole/-indol-3-ol
derivatives.
ACS Omega,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 15, 2025
Herein,
a
DBU-catalyzed
1,6-Michael
addition
of
para-quinone
methides
(p-QMs)
under
mild
reaction
conditions
with
high
efficiency
(turnover
number
up
to
103)
and
good
excellent
yields
is
reported.
The
transformation
proceeds
smoothly
range
nucleophiles,
providing
diverse
diarylmethane
scaffolds
efficiency.
Mechanistic
studies
revealed
that
DBU
an
proton
acceptor
donor
can
promote
the
methanol
p-QMs.
A
preliminary
investigation
was
also
conducted
antibacterial
properties
products.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(14), P. 3807 - 3817
Published: Jan. 1, 2022
A
novel
and
facile
method
for
the
Ag-catalyzed
regioselective
1,6-hydroarylation
of
para
-quinone
methides
(
p
-QMs)
with
anilines
phenols
has
been
established,
a
broad
range
(primary
secondary,
tertiary),
-QMs
are
well
tolerated.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(17), P. 12502 - 12518
Published: Aug. 14, 2023
A
copper-catalyzed
aerobic
oxidative/decarboxylative
phosphorylation
of
aryl
acrylic
acids
with
P(III)-nucleophiles
via
the
Michaelis-Arbuzov
rearrangement
for
synthesis
β-ketophosphine
oxides,
β-ketophosphinates,
and
β-ketophosphonates
is
reported.
The
present
reaction
could
be
conducted
effectively
without
use
a
ligand
base.
Various
kinds
are
tolerated
in
transformation,
generating
desired
β-keto-organophosphorus
compounds
as
valuable
class
phosphorus-containing
intermediates
good
to
excellent
yields.
In
addition,
possible
mechanism
kinetic
studies
have
been
explored
by
step-by-step
control
experiments
competitive
experiments,
results
proved
that
this
transformation
may
follow
second-order
chemical
kinetics
well
involve
radical
process.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(24), P. 16313 - 16327
Published: Dec. 2, 2022
A
Lewis
acid-mediated
one-carbon
homologation
approach
to
installing
a
2-quinolinone
core
embedded
with
para-quinone
methides,
in
high
yield
of
up
92%,
and
regioselectivity
has
been
developed.
Also,
post-synthetic
modifications,
including
C–P,
C–S,
C–C
bond
formations,
have
demonstrated
by
the
1,6-addition
suitable
nucleophiles.
Further,
cyclopropanation
2-quinolinone-embedded
p-QM
is
also
affording
contiguous
quaternary
spiro
center.
Chemistry - An Asian Journal,
Journal Year:
2022,
Volume and Issue:
17(9)
Published: March 5, 2022
An
efficient,
cheap
and
green
protocol
for
the
highly
regioselective
1,6-hydroarylation
of
para-quinone
methides
(p-QMs)
with
indoles
at
C-3
position
has
been
established
by
phosphoric
acid
catalysis
in
water
under
transition-metal-free
reaction
conditions.
A
wide
range
indole
derivatives
are
compatible
reaction,
affording
corresponding
products
good
to
excellent
yields.
The
possible
mechanism
explored
through
step-by-step
control
experiments.
is
convenient
practical
applications,
leading
a
safe,
feasible
way
formation
diarylmethyl
functionalized
derivatives.
