European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(42)
Published: Aug. 25, 2023
Abstract
5‐Halo‐1,2,3‐triazoles
are
important
scaffolds
in
organic
chemistry,
but
current
click
reactions
cannot
produce
1,4,5‐trisubstituted
5‐chloro‐1,2,3‐triazoles
a
simple
way.
Herein,
we
disclosed
Cu(I)‐catalyzed
interrupted
reaction,
using
N
‐chlorophthalimide
as
an
electrophilic
chlorine
source,
enabling
the
facile
synthesis
of
one
step
from
readily
available
terminal
alkynes
and
azides.
Complete
control
regioselectivities
with
broad
substrate
scope
was
accomplished
by
this
approach.
Furthermore,
novel
epoxidation
developed
5‐chloro‐triazole
substrate,
which
could
be
further
applied
various
transformations.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(26), P. 4945 - 4949
Published: June 23, 2023
We
herein
describe
a
three-component
interrupted
click
reaction
to
synthesize
novel
5-pentafluoroethyl
1,2,3-triazoles
in
one
step
from
readily
available
terminal
alkynes
and
azides.
The
key
reagent
[CuCF2CF3],
prepared
the
low-cost
gas
pentafluoroethane,
demonstrates
an
orthogonal
reactivity
facilitating
cycloaddition
rather
than
previously
reported
radical
reactions.
Reaction
conditions
are
mild
by
using
air
as
green
oxidant.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 18, 2025
The
1,2,3-triazole
scaffolds
are
an
important
class
of
biologically
privileged
heterocyclic
compounds
with
several
key
applications
in
chemistry,
biology,
medicine,
agriculture,
and
material
science.
"postclick"
functionalization
1,2,3-triazoles
may
emerge
as
a
promising
tactic
for
the
construction
molecular
architectures
therapeutics
is
considered
to
be
growing
area
investigation.
This
interest
extends
beyond
regioselective
Cu(I)-catalyzed
azide-alkyne
cycloaddition
(CuAAC)
method
that
involves
trapping
Cu(I)-triazole
suitable
precursors.
In
this
Perspective,
we
highlight
impact
postclick
strategies
organic
synthesis
required
late-stage
hope
emerging
concept
provide
ample
opportunities
modern
notable
medicinal
materials
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(20)
Published: Feb. 26, 2024
Abstract
The
particular
and
unique
mechanism
of
the
copper‐catalyzed
reaction
between
azides
alkynes
(CuAAC)
has
not
only
allowed
for
efficient
synthesis
1,2,3‐trisubstituted
1,4‐triazoles
in
excellent
yields
under
mild
conditions,
becoming
quintessential
click
reaction,
but
it
also
enabled
straightforward
formation
a
metallocycle
intermediate,
copper
triazolyl.
This,
suitable
conditions
able
to
suppress
its
protonolysis,
can
be
used
either
creation
new
bicyclic
triazolyl
structures
or
generation
novel
three
four‐component
reactions.
aim
this
review
is
rationalize
unify
all
these
transformations,
which
are
collectively
referred
as
“interrupted
reactions”.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(32), P. 6443 - 6484
Published: Jan. 1, 2024
Alkynes
are
important
in
organic
synthesis.
This
review
mainly
focuses
on
the
recent
advances
(2013–2023)
alkynes
with
C–S
bond
formation,
based
more
than
30
kinds
of
sulfur
reagents.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(11), P. 2233 - 2237
Published: March 14, 2024
We
document
the
intramolecular
interception
of
a
Cu-catalyzed
azidoalkyne
cycloaddition
employing
suitably
placed
nitrone
group,
providing
simple
route
to
unprecedented
spiro-polyheterocyclic
scaffold.
The
reaction
is
comprised
[3
+
2]-cycloaddition
(2-azidoaryl)isatogen
with
terminal
alkyne
and
trapping
transient
Cu-triazolide
intermediate
isatogen,
net
formation
one
C–C
two
C–N
bonds
new
heterocyclic
ring
being
spiro-annulated.
Abstract
Alkynes
are
simple
yet
important
organic
feedstocks.
The
selenylation
of
alkynes
is
able
to
produce
complex
selenium‐containing
compounds
in
a
facile
way.
Although
there
some
reviews
about
the
alkynes,
most
them
focus
on
one
specific
reaction
or
what
types
products
that
can
be
obtained.
There
lack
attention
given
various
uses
different
selenium
reagents
and
their
mechanisms.
This
review
mainly
focuses
recent
advances
(2013–2023)
based
diverse
reagents.
Mechanisms
how
added
work
will
discussed.
Different
types,
including
difunctionalization,
Se‐annulation,
spiro‐cyclization,
C−Se
coupling,
click
recorded
this
review.
regioselectivity
achieved
through
mechanisms,
radicals,
seleniraniums
electrophilic
cyclization.
We
hope
it
do
help
for
future
research
area.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(46)
Published: Aug. 28, 2024
Abstract
Alkynes
are
valuable
building
blocks
in
organic
synthesis.
They
can
undergo
three‐component
difunctionalization
to
create
sulfur
or
selenium‐containing
compounds.
Three‐component
reactions
of
alkynes
atom
economic,
practical
and
regioselective.
This
review
will
disscuss
decade
developments,
including
C−S
C−Se
bond
formation
via
thiolation,
sulfonylation
selenylation.
Recent
developments
be
mainly
categorized
into
three
types.
(1)
Radical
C−S/S−Se
is
a
hot
topic.
Reactions
initiated
by
S/Se
radicals
other
exhibit
two
types
selectivities.
Photochemical
electrochemical
under
eco‐friendly
conditions
have
been
increasingly
reported.
(2)
Some
transformations
involve
electrophilic
three‐membered
ring
intermediates.
Thiiraniums,
seleniraniums,
iodoniums
among
the
most
prevalent
species.
ring‐opening
various
nucleophiles
participate
tandem
reactions.
(3)
Metal‐catalyzed
reactions,
classic
category,
also
discussed
text.
In
following
section,
we
provide
an
overview
based
on
mechanisms
substrates.
The
roles
added
reagents
discussed.
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(11)
Published: Sept. 8, 2023
Abstract
An
efficient
method
for
the
synthesis
of
N
‐alkylated
1,2,3‐triazoles
from
NH
‐1,2,3‐triazoles
and
alcohols
was
developed
by
utilizing
Lewis
or
Brønsted
acid
as
a
catalyst.
The
reaction
demonstrates
mild
conditions,
straightforward
operation,
92–97
%
overall
yield.
Allylic
triphenyl
methanol
together
with
1,1‐diphenylethan‐1‐ol
gave
single
2
‐substituted
products,
while
regioselectivities
reactions
aryl‐substituted
secondary
alcohols,
including
diarylmethanols,
1‐phenylethanol,
were
controlled
electronic
effect
spatial
hindrance
‐1,2,3‐triazoles.
Furthermore,
tert
‐butanol
always
low
regioselectivites
different
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
27(6)
Published: Dec. 15, 2023
Abstract
Sulfur‐containing
1,2,3‐triazoles
display
bioactivities
like
antidepressant,
antifungal
activity,
antitumor,
etc.
Numerous
approaches
have
been
established
to
form
sulfur‐containing
1,2,3‐triazoles.
4‐Sulfanyl‐
and
5‐sulfanyl‐1,2,3‐triazoles
were
produced
by
metal‐catalyzed
azide‐alkyne
cycloaddition
(AAC),
N
‐Sulfonyl‐1,2,3‐triazoles
generated
via
the
reaction
of
acetylides
with
sulfonyl
azides,
CuAAC.
4‐Sulfonyl‐1,2,3‐triazoles
through
[3+2]
azide
bromovinylsulfonyl
fluoride.
Although
5‐sulfonyl‐1,2,3‐triazoles
formed
successfully
RuAAC,
their
synthetic
very
limited.
1‐Phosphinyl‐2‐sulfanylethynes
suitable
substances
access
sulfur‐
phosphorus‐containing
triazoles.
In
this
review,
synthesis
properties
highlighted.
Initially,
organosulfurs,
briefly
introduced.
After
stating
general
procedures
construct
1,2,3‐triazole
skeleton,
sulfur‐involved
sorted
described
in
details.
According
different
kinds
1,2,3‐triazoles,
methods
features
4‐sulfanyl‐1,2,3‐triazoles,
5‐sulfanyl‐1,2,3‐triazoles,
‐sulfonyl‐1,2,3‐triazoles,
4‐sulfonyl‐1,2,3‐triazoles,
5‐sulfonyl‐1,2,3‐triazoles,
heteroatom‐containing
summarized.
