Frontiers in Chemistry,
Год журнала:
2024,
Номер
12
Опубликована: Фев. 19, 2024
This
comprehensive
review,
covering
2021-2023,
explores
the
multifaceted
chemical
and
pharmacological
potential
of
coumarins,
emphasizing
their
significance
as
versatile
natural
derivatives
in
medicinal
chemistry.
The
synthesis
functionalization
coumarins
have
advanced
with
innovative
strategies.
enabled
incorporation
diverse
functional
fragments
or
construction
supplementary
cyclic
architectures,
thereby
biological
physico-chemical
properties
compounds
obtained
were
enhanced.
unique
structure
coumarine
facilitates
binding
to
various
targets
through
hydrophobic
interactions
pi-stacking,
hydrogen
bonding,
dipole-dipole
interactions.
Therefore,
this
important
scaffold
exhibits
promising
applications
uncountable
fields
chemistry
(e.g.,
neurodegenerative
diseases,
cancer,
inflammation).
Organic Letters,
Год журнала:
2023,
Номер
25(47), С. 8451 - 8456
Опубликована: Ноя. 16, 2023
The
three-component
reactions
of
enaminones,
disulfides,
and
alcohols
for
the
synthesis
polyfunctionalized
alkenes
have
been
realized
via
C-H
C-N
bond
transformation
on
enaminones.
proceed
in
a
novel
"alkene-to-alkene"
difunctionalization
mode
without
using
any
transition
metal.
application
alkene
products
divergent
sulfenyl
heteroaryls,
including
sulfenylated
pyrazoles,
pyrimidines,
isoxazoles,
simple
annulation
has
also
verified.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
62(8)
Опубликована: Дек. 22, 2022
Efficient
protocols
for
accessing
iodo-substituted
diaryl
and
aryl(vinyl)
sulfides
have
been
developed
using
iodonium
salts
as
reactive
electrophilic
arylation
vinylation
reagents.
The
reactions
take
place
under
transition-metal-free
conditions,
employing
odorless
convenient
sulfur
A
wide
variety
of
functional
groups
are
tolerated
in
the
S-diarylation,
enabling
regioselective
late-stage
application
several
heterocycles
drug
molecules
mild
reaction
conditions.
novel
S-difunctionalization
pathway
was
discovered
vinyliodonium
salts,
which
proceeds
additive-free
conditions
grants
excellent
stereoselectivity
synthesis
sulfides.
one-pot
strategy
combining
diarylation
subsequent
reduction
provided
facile
access
to
electron-rich
thioanilines
a
direct
potential
candidate
derivative.
retained
iodo
group
allows
array
further
synthetic
transformations.
Mechanistic
insights
were
elucidated
by
isolating
key
intermediate,
relevant
energy
profile
substantiated
DFT
calculations.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(16), С. 2751 - 2756
Опубликована: Май 5, 2023
Abstract
Our
group
has
reported
several
one‐pot
protocols
for
the
synthesis
of
diaryliodonium
salts,
which
have
been
recognized
as
attractive
multi‐purpose
reagents
in
areas
ranging
from
organic
to
materials
chemistry.
Over
years,
we
identified
limitations
published
concerning
mixed
electron‐rich
and
electron‐poor,
well
highly
electron‐poor
corresponding
starting
are
either
too
reactive
or
unreactive.
In
this
update,
discuss
underlying
stability
reactivity
involved
provide
strategies
overcome
these
challenges
through
updated
synthetic
protocols.
The Chemical Record,
Год журнала:
2023,
Номер
23(10)
Опубликована: Май 30, 2023
Abstract
Our
research
interest
focusing
on
synthetic
methodology
with
diaryliodonium
salts,
is
summarized
in
this
account.
Besides
employing
a
dual
activation
strategy
of
C−I
and
ortho
C−H
bonds,
we
have
introduced
vicinal
functional
groups
at
‐positions
which
their
unique
reactivities
been
explored
various
processes,
including
arylation,
diarylation,
cascade
annulation,
benzocyclization,
arylocyclization,
intramolecular
aryl
migration.
The
variety
mechanisms
these
reactions
that
involves
either
transition
metals,
especially
palladium
organometallic
catalysis,
or
transition‐metal
free
conditions,
were
discussed
the
context.
Chem,
Год журнала:
2024,
Номер
10(9), С. 2901 - 2915
Опубликована: Июнь 27, 2024
The
synthesis
of
organochalcogenides
remains
a
valuable
area
research
due
to
their
widespread
biological
applications,
particularly
in
pharmaceuticals.
Herein,
our
study
details
the
B(C6F5)3-catalyzed
Csp2–H
functionalization
diverse
arenes,
heteroarenes,
and
pharmacophores
with
thiosuccinimides
or
selenosuccinimides,
providing
selective
access
chalcogenated
products.
This
protocol
enables
late-stage
chalcogenation
drug
molecules
such
as
anti-inflammatory
naproxen,
estrogen
steroid
hormone
estradiol
derivatives,
industrially
relevant
trifluoromethylthiolation
reaction.
Furthermore,
this
C–S
coupling
methodology
provides
facile
metal-free
route
synthesize
vortioxetine,
an
antidepressant
drug,
plethora
significant
organic
motifs.
Detailed
NMR,
EPR
analyses,
density
functional
theory
(DFT)
computational
studies
indicate
that
elongation
thiosuccinimide
N–S
bond
is
assisted
by
boron-centered
adduct,
which
then
leads
stable
ion
pair
arene.
analysis
shows
transient
radical
pair,
potentially
off-cycle
species,
not
directly
involved
catalytic
process.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(28)
Опубликована: Май 17, 2023
The
Truce-Smiles
rearrangement
is
an
intramolecular
SN
Ar
reaction,
enabling
the
formation
of
a
new
arene
carbon-carbon
bond
with
sufficiently
strong
carbon-centered
nucleophile.
Reported
here
are
ortho-tosylmethylene
functionalized
diaryliodonium
salts,
which
can
undergo
unprecedented
in
ionic
liquids,
resulting
sulfonyl-substituted
ortho-iodo
diarylmethanes
as
powerful
class
building
blocks
chemical
synthesis.
protocol
features
aryliodo
moiety
hyper
nucleofuge,
facilitating
Meisenheimer
complex
within
migratory
system.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(48)
Опубликована: Окт. 17, 2023
The
diarylation
and
skeletal
diversification
of
unstrained
cyclic
amines
was
exploited
to
expand
modify
the
favorable
properties
this
important
substrate
class
with
pivotal
roles
in
drug
discovery.
Cyclic
were
employed
synthesis
a
novel
amino-substituted
diaryliodonium
salts,
which
converted
highly
functionalized
diarylamines
through
an
atom-efficient
one-pot
N-arylation/ring
opening
reaction
external
nucleophiles.
proceeds
situ
formation
diarylammonium
intermediate
that
undergoes
nucleophilic
ring
by
cleavage
strong
C-N
bond.
A
wide
variety
obtained
introduction
two
different
aryl
groups
varied
electronics,
retained
iodo-substituent
enables
downfield
diversifications
products.
More
than
20
nucleophiles,
including
amines,
phenols,
carboxylic
acids,
thiols
halides,
alkylated
high
functional
group
tolerance,
strategy
proved
efficient
also
late-stage
functionalization
natural
products
pharmaceuticals.
JACS Au,
Год журнала:
2024,
Номер
4(8), С. 2832 - 2837
Опубликована: Авг. 5, 2024
Herein,
we
disclose
a
convenient
protocol
for
the
α-diarylation
of
carbon
nucleophiles
to
yield
heavily
functionalized
quaternary
products.
Diaryliodonium
salts
are
utilized
transfer
both
aryl
groups
under
transition-metal-free
conditions,
which
enables
an
atom-efficient
and
high-yielding
method
with
broad
functional
group
tolerance.
The
methodology
is
amenable
wide
variety
can
be
in
late-stage
functionalization
complex
arenes.
Furthermore,
it
compatible
new
class
zwitterionic
iodonium
reagents,
gives
access
phenols
