New Journal of Chemistry,
Journal Year:
2022,
Volume and Issue:
46(35), P. 16832 - 16839
Published: Jan. 1, 2022
A
metal-free
and
efficient
protocol
has
been
developed
for
sequential
oxidation
followed
by
acetoxylation/tosylation
of
α-alkylbenzylamines
the
synthesis
α-acyloxy/tosyloxy
ketones
using
hypervalent
iodine(
iii
).
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.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(21), P. 3666 - 3673
Published: Sept. 14, 2023
Abstract
Sulfoximines,
the
isoelectronic
with
sulfones,
represent
a
class
of
alternative
and
intriguing
motifs
in
both
discovery
program
agrochemistry.
N
‐Alkylation
on
imines
could
significantly
improve
their
bioactivities,
but
lack
general
method
has
hindered
further
uptake
by
medicinal
chemistry
drug
development.
Herein,
we
present
mild
photocatalytic
anti‐Markovnikov
hydroamination
alkenes
to
construct
‐alkylated
sulfoximines
broad
substrate
tolerance
primary,
secondary
tertiary
alkyl
substituents
as
well
diverse
range
sulfoximines.
The
mechanistic
studies
support
pathway,
demonstrate
that
alkene
radical
cation
rather
than
iminium
serves
key
intermediate
transformation.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(9), P. 1549 - 1554
Published: March 16, 2022
Abstract
A
metal
and
base‐free,
operationally
simple,
scalable
multicomponent
approach
towards
the
synthesis
of
S
‐diarylmethane
dithiocarbamates
is
reported.
range
structurally
electronically
diverse
p
‐quinone
methides
are
shown
to
react
with
a
variety
amines,
carbon
disulfide
furnish
corresponding
in
good
excellent
yields
under
mild
conditions.
Furthermore,
‐QMs
embedded
aliphatic
substituents
well
accommodated.
Importantly,
these
readily
accessible
compounds
demonstrated
promising
anti‐proliferative
activity
low
micromolar
ranges
lung
adenocarcinoma
cells,
reiterating
importance
developed
methodology.
magnified
image
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(6), P. 820 - 825
Published: Feb. 22, 2023
Pd(II)-Catalyzed,
bidentate
directing
group
(BDG)-assisted
C(sp2)−H
functionalization
of
C2-amido
glycals
onto
the
anomeric
position
is
described
as
a
contemporary
method
for
construction
various
unsymmetrical
gem-diarylmethyl
C-glycosides.
Thanks
to
amidoquinoline-type
group,
insertion
diverse
para-quinone
methides
(p-QMs)
pseudo-anomeric
glycal
substrates
were
executed
in
moderate
good
yields.
Further
final
product
can
be
successfully
demonstrated
by
known
palladium-catalyzed
cross-coupling
reactions.
As
service
our
authors
and
readers,
this
journal
provides
supporting
information
supplied
authors.
Such
materials
are
peer
reviewed
may
re-organized
online
delivery,
but
not
copy-edited
or
typeset.
Technical
support
issues
arising
from
(other
than
missing
files)
should
addressed
Please
note:
The
publisher
responsible
content
functionality
any
Any
queries
content)
directed
corresponding
author
article.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(22), P. 3830 - 3836
Published: Oct. 6, 2023
Abstract
Herein,
electrochemical
reductive
carboxylation
of
para
‐quinone
methides
with
CO
2
was
developed.
A
variety
value‐added
carboxylic
acids
can
be
accessed
in
moderate
to
excellent
yields.
Preliminary
studies
showed
that
were
reduced
benzyl
carbanion
during
the
reaction.
This
protocol
features
high
atom
economy,
operational
simplicity,
and
environmental
friendliness,
enabling
synthesis
various
compounds.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(3), P. 1695 - 1712
Published: Jan. 12, 2023
Herein,
we
invented
the
Cs2CO3-mediated
atom
economic
method
that
streamlines
scission
of
C(O)–S/Se
bond
involving
in
situ
generation
an
anomeric
thiolate/selenolate
anion,
which
reacted
with
p-QMs
to
yield
novel
unsymmetrical
gem-diarylmethylthio/seleno
glycosides
while
retaining
stereochemistry.
Notably,
key
features
this
protocol
involve
unprecedented
long-range
acyl
transfer
(from
S/Se
O),
thus
affording
acylation
final
product
is
not
yet
reported
by
classical
methods.
This
straightforward
offers
a
mild,
short
reaction
time,
synthetically
simple
approach,
and
compatibility
8
types
sugar
along
phenylthio/benzylseleno
esters.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(23), P. 17090 - 17100
Published: Nov. 11, 2021
A
series
of
indolyl
or
imidazo[1,2-a]pyridinyl-substituted
para-quinone
methides
(p-QMs)
is
prepared
by
a
metal-free,
TEMPO-mediated
cross-dehydrogenative
coupling
butylated
hydroxytoluene
(BHT)
with
indoles
imidazo[1,2-a]pyridines
in
good
to
high
yields.
Broad
substrate
scope
respect
and
imidazo[1,2-a]pyridines,
functional
group
tolerance,
acid/base-free
conditions
are
advantageous
feature
the
developed
protocol.
The
method
was
amenable
for
scale-up
on
gram
scale.
Based
control
experiments,
reaction
mechanism
proposed
describe
this
transformation.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(12), P. 2518 - 2529
Published: Jan. 1, 2022
Scandium
triflate
(Sc(OTf)3)
catalyzed,
mild,
and
regioselective
ring-opening
reaction
of
donor-acceptor
(D-A)
cyclopropanes
has
been
developed
using
sulfoximines
for
the
synthesis
γ-sulfoximino
malonic
diesters.
This
protocol
allows
different
N-alkyl
in
good
to
excellent
yields
(up
94%)
with
broad
functional
group
tolerance.
In
this
process,
N-H
C-C
bonds
are
cleaved
form
new
C-N
C-H
bonds.
The
feasibility
method
is
supported
by
a
gram-scale
synthetic
elaboration
obtained
product.