Synthesis,
Год журнала:
2022,
Номер
54(11), С. 2548 - 2560
Опубликована: Март 1, 2022
Abstract
The
widespread
use
of
1,2,3-triazole
compounds
in
drugs
has
resulted
a
great
interest
the
efficient
synthesis
N2-substituted
1,2,3-triazoles
via
post
triazole
functionalization
methods.
At
present,
there
are
many
methods
for
N1-substituted
compounds,
but
development
convenient
N2-selective
remains
challenging.
In
general,
greater
stability
N1
tautomer
makes
N2
position
non-preferable
reactive
site,
which
limited
application
1,2,3-triazoles.
this
review,
we
summarized
advances
direct
since
2008.
1
Introduction
2
N2-Alkylation
3
N2-Allylation
4
N2-Propargylation
5
N2-Alkenylation
6
N2-Alkynylation
7
N2-Arylation
8
Conclusions
and
Outlook
ACS Sustainable Chemistry & Engineering,
Год журнала:
2021,
Номер
9(27), С. 8895 - 8918
Опубликована: Июнь 25, 2021
The
development
of
new
sustainable
reactions
and
protocols
is
essential
to
fulfill
the
growing
demands
every
branch
organic
chemistry
for
greener
synthetic
methodologies.
In
this
context,
use
visible
light
as
only
source
energy
highly
appealing.
Since
diazo
compounds
are
valuable
reagents
in
synthesis,
their
transformations
realized
a
manner
interest.
High
reactivity
easy
availability
make
them
suitable
solar-driven
transformations.
Indeed,
photochemical
have
recently
proven
alternative
transition
metal
catalysis.
perspective,
we
highlight
applications
these
under
irradiation,
particularly
focusing
on
recent
advancements.
These
include
generation
carbenes
radicals
which
involve
many
relevant
reactions,
[2+1]-cycloadditions,
X–H
C–H
insertions,
Wolff
rearrangement,
more.
Mechanistic
aspects
processes
briefly
addressed
give
readers
deeper
understanding
rules
underlying
photoreactivity
compounds.
We
conclude
by
emphasizing
significant
advancements
discussing
challenges
future
developments
photochemistry
reagents.
Chemical Reviews,
Год журнала:
2024,
Номер
124(11), С. 7214 - 7261
Опубликована: Май 16, 2024
In
recent
years,
visible
light-induced
reactions
of
diazo
compounds
have
attracted
increasing
attention
in
organic
synthesis,
leading
to
improvement
existing
reactions,
as
well
the
discovery
unprecedented
transformations.
Thus,
photochemical
or
photocatalytic
generation
both
carbenes
and
radicals
provide
milder
tools
toward
these
key
intermediates
for
many
valuable
However,
vast
majority
transformations
represent
new
reactivity
modes
compounds,
which
are
achieved
by
decomposition
photoredox
catalysis.
particular,
use
a
redox-active
photocatalysts
opens
avenue
plethora
radical
reactions.
The
application
methods
led
inaccessible
classical
associated
with
metal
carbenes.
most
cases,
act
sources
but
can
also
serve
acceptors.
Importantly,
described
processes
operate
under
mild,
practical
conditions.
This
Review
describes
this
subfield
compound
chemistry,
particularly
focusing
on
advancements.
Chinese Journal of Organic Chemistry,
Год журнала:
2021,
Номер
41(12), С. 4565 - 4565
Опубликована: Янв. 1, 2021
Carbene
is
one
of
the
most
important
synthetic
intermediates
in
organic
synthesis.In
past
few
decades,
transition-metal
catalyzed
carbene
transfer
reactions
have
made
remarkable
development.Recently,
visible
light-promoted
transformation
diazo
compounds
through
formation
free
as
key
intermediate
begun
to
rise.The
reaction
only
need
light
sole
energy
source
which
meets
concept
green
chemistry.Since
pioneering
works
developed
by
groups
Diaves
and
Zhou,
photo-promoted
has
attracted
more
attentions.On
basis
previous
work,
latest
progress
this
field
further
improved,
mainly
focuses
on
recent
new
under
irradiation
contributions
reported
from
Chinese
research
group.The
future
development
direction,
well
challenges
prospected.
Chemical Communications,
Год журнала:
2022,
Номер
58(28), С. 4435 - 4455
Опубликована: Янв. 1, 2022
Indazole
and
pyrazole
are
renowned
as
a
prodigious
class
of
heterocycles
having
versatile
uses
in
medicinal
well
industrial
chemistry.
Considering
sustainable
approaches,
recently,
photocatalysis
has
become
an
indispensable
tool
organic
chemistry
due
to
its
application
for
the
activation
small
molecules
use
clean
energy
source.
In
this
review,
we
have
highlighted
metal-based
photocatalysts,
photoredox
catalysts,
transfer
photocatalysts
electron-donor-acceptor
complexes
functionalization
indazole
pyrazole.
This
perspective
is
arranged
based
on
types
reactions
A
detailed
discussion
regarding
reaction
mechanism
each
given
provide
comprehensive
guide
reader.
Finally,
summary
existing
challenges
future
outlook
towards
development
efficient
photocatalytic
methods
these
also
presented.
Organic Letters,
Год журнала:
2024,
Номер
26(4), С. 933 - 938
Опубликована: Янв. 19, 2024
A
visible-light-induced
highly
efficient
C(sp3)–H
amination
of
ethers
with
amides
and
azoles
has
been
presented
under
mild
conditions
via
a
nitrogen-
carbon-centered
radical
coupling
process.
This
protocol
successfully
utilizes
2,3-dichloro-5,6-dicyano-p-benzoquinone
(DDQ)
tert-butyl
nitrite
(TBN)
as
cocatalysts
to
deliver
the
aminated
products
aerobic
conditions.
Notably,
developed
reaction
features
corresponding
in
good
yields
(up
93%)
wide
substrate
scope.
The
mechanistic
study
indicates
that
C–N
bond
formation
proceeds
direct
cross-coupling
Preliminary
biological
activity
analysis
resulting
have
selective
inhibitory
on
osteosarcoma
(OS)
cell
lines
are
promising
for
use
hits
drug
discovery.
Organic Letters,
Год журнала:
2020,
Номер
22(21), С. 8407 - 8412
Опубликована: Окт. 13, 2020
A
visible-light-mediated
protocol
for
the
hydroacylation
of
azobenzenes
with
α-keto
acids
has
been
developed.
In
absence
any
catalyst
or
additive,
decarboxylative
proceeded
smoothly
under
visible-light
irradiation
at
room
temperature.
wide
range
and
were
well-tolerated
afforded
products
in
high
to
excellent
yields.
Preliminary
investigations
indicated
that
photoactive
absorb
visible
light
enable
transformation.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(5), С. 1321 - 1326
Опубликована: Янв. 1, 2022
A
visible
light-mediated
strategy
insensitive
to
air
or
moisture
allows
a
3-component
reaction
between
aryldiazoacetates,
cyclic
ethers
and
various
nucleophiles
afford
formal
O–H
inserted
products
of
more
complex
alcohols.
Organic Letters,
Год журнала:
2022,
Номер
24(7), С. 1530 - 1535
Опубликована: Фев. 14, 2022
A
visible-light-promoted
aerobic
oxyphosphorylation
of
α-diazoesters
and
H-phosphine
oxides
has
been
developed.
Using
air
as
the
oxygen
source,
reaction
proceeded
smoothly
at
room
temperature
under
blue-light
irradiation.
The
α-diazoesters,
molecular
oxygen,
are
conveniently
incorporated
into
a
C-O-P(O)
unit
in
one
step.
preliminary
mechanistic
studies
indicated
that
light-triggered
radical
process
is
involved.
developed
strategy
shows
unrevealed
reactivity
diazo
compounds
with
potential
value
synthetic
applications.
Organic Letters,
Год журнала:
2021,
Номер
23(9), С. 3409 - 3414
Опубликована: Апрель 12, 2021
An
unprecedented
visible
light-assisted
and
zinc
triflate-catalyzed
construction
of
a
diaryl-substituted
quaternary
stereocenter
is
reported.
2-(4-Hydroxyphenyl)-substituted
aldehydes
ketones
have
been
prepared
in
moderate
to
high
yields
via
multicomponent
reaction
acetylene,
benzoquinone
(BQ),
indole/aniline/thiol.
The
believed
proceed
situ
generation
p-quinone
methide
through
[2+2]
cycloaddition–retroelectrocyclization
BQ
acetylene
blue
light
followed
by
vinylogous
Michael
addition
with
nucleophiles.
Organic Letters,
Год журнала:
2022,
Номер
24(31), С. 5855 - 5859
Опубликована: Авг. 2, 2022
A
visible
light-promoted
generation
of
nitrilium
ions
from
diazoacetates
and
nitriles
has
been
developed.
The
reaction
utilized
light
transformation
to
the
free
carbene
that
could
be
trapped
by
generate
ions,
followed
nucleophilic
attack
on
benzotriazoles
carboxylic
acids.
This
protocol
provides
an
efficient
practical
approach
N-imidoylbenzotriazoles
diacylglycine
esters
in
good
excellent
yields.
