Chinese Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
42(11), P. 3835 - 3835
Published: Jan. 1, 2022
Pyrimidine
aryl
ether
derivatives
have
attracted
widespread
attention
from
chemists
for
their
diverse
biological
activity
and
pharmacological
properties.In
this
paper,
a
series
of
pyrimidine-2-arylether
were
synthesized
with
moderate
to
good
yield
by
using
2-(trimethylsilyl)phenyl
trifluoromethanesulfonate
as
source
benzyne
react
2-hydroxypyrimidine.Compared
the
traditional
method,
method
has
advantages
transition-metal-free,
easy
preparation
2-aryloxypyrimidine
derivatives,
wide
functional
group
compatibility
high
yield.
Chemical Reviews,
Journal Year:
2024,
Volume and Issue:
124(20), P. 11435 - 11522
Published: Oct. 9, 2024
Arynes
hold
significance
for
the
efficient
fusion
of
(hetero)
arenes
with
diverse
substrates,
advancing
construction
complex
molecular
frameworks.
Employing
multiple
equivalents
arynes
is
particularly
effective
in
rapid
formation
polycyclic
cores
found
optoelectronic
materials
and
bioactive
compounds.
However,
inherent
reactivity
often
leads
to
side
reactions,
yielding
unanticipated
products
underlining
importance
a
detailed
investigation
into
use
fine-tune
their
reactivity.
This
review
centers
on
methodologies
syntheses
organic
reactions
involving
arynes,
categorizing
based
mechanisms
like
cycloadditions,
σ-bond
insertions,
nucleophilic
additions,
ene
discusses
aryne
polymerization.
The
categorization
these
includes
two
primary
approaches:
first
entails
engagement
within
single
step
while
second
approach
involves
using
equivalent
sequentially
across
steps,
both
requiring
strict
control
ensure
precise
participation
each
respective
step.
Additionally,
provides
an
in-depth
analysis
selection
precursors,
organized
chronologically
by
activation
strategy,
offering
comprehensive
background
that
supports
main
theme
utilization.
expectation
remains
this
will
be
invaluable
designing
advanced
engaging
arynes.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(9), P. 1891 - 1895
Published: Feb. 26, 2024
Pseudocyclic
arylbenziodoxaboroles
are
unique
aryne
precursors
under
neutral
aqueous
conditions
that
selectively
react
with
organic
sulfides,
forming
the
corresponding
sulfonium
salts.
This
reaction
is
compatible
various
substituents
(alkyl,
halogen,
CN,
NO
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(18), P. 3816 - 3821
Published: April 30, 2024
A
new
method
to
synthesize
o-bromobenzenethiol
equivalents
through
aryne
intermediates
is
disclosed.
Various
are
prepared
by
the
bromothiolation
of
with
potassium
xanthates.
Aryl
xanthates
serve
in
synthesis
diverse
organosulfurs
involving
phenothiazines
and
thianthrenes
further
transformations.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(7), P. 1538 - 1544
Published: Feb. 8, 2024
Abstract
Herein
we
report
a
method
for
the
synthesis
of
thioethers
by
forging
C(aryl)‐S
bond
via
an
aryne
mechanism.
The
active
species
can
be
generated
from
o
‐diiodoarenes
and
NaH
in
THF
at
room
temperature,
then
lead
to
arylations
wide
range
aryl
thiols
thioureas.
Different
transition
metal‐catalyzed
cross‐coupling
reactions,
no
disubstituted
byproduct
is
formed
our
protocol.
‐iodoaryl
thioether
products
are
intermediates
that
could
transformed
into
pharmaceutically
interesting
molecules.
Synthesis,
Journal Year:
2022,
Volume and Issue:
54(22), P. 5064 - 5076
Published: Jan. 24, 2022
Abstract
Aryne
chemistry
is
a
powerful
synthetic
technique
that
forms
new
bonds
to
aromatic
rings.
The
recent
resurgence
of
aryne-based
multicomponent
coupling
strategies
has
led
an
influx
methodologies
for
the
mild
synthesis
arene
derivatives.
In
particular,
these
innovative
discoveries
broaden
and
streamline
approaches
toward
phenol
ether
motifs,
which
are
prevalent
structural
component
across
broad
range
related
research
fields.
Herein,
this
review
aims
provide
comprehensive
overview
progress
in
construction
C(sp2)–O
via
aryne-induced
reactions.
Special
attention
been
paid
reaction
design
mechanistic
pathways.
1
Introduction
2
Insertion-Based
MCRs
3
Nucleophilic-Addition-Based
4
Cycloaddition-Based
5
Summary
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(4), P. 2666 - 2669
Published: Jan. 26, 2023
N-Alkyl
sulfoximines
react
with
arynes
generated
in
situ
under
mild
conditions
providing
o-sulfinylanilines
good
yields.
The
transformation
is
characterized
by
a
broad
substrate
scope
and
functional
group
tolerance.
structure
of
reaction
product
was
confirmed
single-crystal
X-ray
diffraction.
Synthesis,
Journal Year:
2022,
Volume and Issue:
54(22), P. 4932 - 4962
Published: May 30, 2022
Abstract
Carbocycles
and
heterocycles
are
highly
relevant
structural
moieties
that
have
found
countless
applications
in
interdisciplinary
areas.
In
this
regard,
the
interesting
chemistry
of
arynes
has
been
embraced
by
researchers
for
synthesis
structurally
different
polycyclic
systems,
i.e.
carbocycles
heterocycles.
review,
we
intended
to
provide
a
comprehensive
overview
on
annulative
approach
considering
Kobayashi’s
aryne
intermediate
as
key
reactive
species
with
diverse
nucleophilic
electrophilic
partners.
The
review
highlights
annulation
reactions
adopted
(covering
articles
mainly
from
around
2010),
showcasing
their
viability
towards
broad
range
substrates
bearing
functionalities.
1
Introduction
2
Synthesis
3
Heterocycles
4
Conclusions
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(39)
Published: Aug. 19, 2023
Abstract
Sulfonyl
chlorides
are
a
class
of
cheap
and
readily
available
basic
chemicals,
which
have
routinely
served
as
electrophilic
reagents
in
their
chemical
transformations.
Herein,
we
disclose
novel
PPh
3
‐mediated
nucleophilic
sulfonation
method
sulfonyl
with
arynes.
Different
from
the
classical
P(III)‐mediated
reductive
deoxygenation
reaction
chlorides,
valence
state
sulfur
atom
has
not
been
changed.
This
protocol
exhibits
broad
functional
group
tolerance
provides
direct
approach
to
variety
aryl
alkyl
sulfones.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Aug. 30, 2024
An
aryne-promoted
dehydrosulfurization
reaction
of
thioamides
to
give
nitriles
and
diaryl
sulfides
in
a
one-pot
manner
is
presented.
Aromatic,
heteroaromatic,
aliphatic
natural
products
drug-derived
were
obtained
good
excellent
yields.
Especially,
selenoamide
was
also
suitable
substrate
produced
selenide
nitrile
high
The
D-labeled
experiments
indicated
that
the
protons
transfer
sulfides.
Synthesis,
Journal Year:
2022,
Volume and Issue:
54(22), P. 5003 - 5016
Published: April 1, 2022
Abstract
The
use
of
arynes
as
highly
reactive
intermediates
has
attracted
substantial
attention
in
organic
synthesis.
To
enhance
the
utility
arynes,
regiocontrol
reactions
unsymmetrically
substituted
is
an
important
task.
introduction
halogen
substituent
at
3-position
leads
to
sufficient
for
various
synthetic
reactions.
This
short
review
highlights
3-haloarynes
synthesis
and
discusses
distortion
models
used
explain
regioselectivity,
representative
3-haloarynes
generated
from
polyhaloarenes,
preparation
easily
activatable
aryne
precursors.
1
Introduction
2
Distortion
Models
3
Reaction
Precursors
Activated
by
Organometallic
Reagent
or
Base
4
Preparation
Easily
Activatable
5
Reactions
6
Concluding
Remarks
