The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(19), P. 12921 - 12931
Published: Sept. 21, 2022
A
simple
visible-light-initiated
strategy
has
been
established
for
the
construction
of
organophosphorus
compounds
via
aerobic
multicomponent
reaction
α-diazoesters,
cyclic
ethers,
and
P(O)H
under
air.
number
phosphonates
phosphinates
could
be
efficiently
isolated
in
moderate
to
good
yields
without
use
photosensitizers
metal
reagents.
This
advantages
mild
condition,
operation,
eco-friendly
energy,
functional-group
tolerance,
gram-scale
synthesis.
Chemical Society Reviews,
Journal Year:
2020,
Volume and Issue:
49(19), P. 6833 - 6847
Published: Jan. 1, 2020
Carbenes
are
important
intermediates
in
organic
chemistry
and
have
been
widely
applied
various
types
of
reactions,
ranging
from
cycloaddition
reactions
sigmatropic
rearrangements
to
C-H
functionalizations,
thus
allowing
the
rapid
construction
densely
functionalized
molecules.
Over
past
decades,
remarkable
progress
has
achieved
metal-catalyzed
carbene
transfer
reactions.
Nevertheless,
realizing
these
transformations
under
milder
and/or
greener
conditions
is
still
highly
desirable.
Only
recently,
visible
light-promoted
diazo
compounds
via
free
emerged
as
a
practical,
mild
powerful
tool.
In
this
tutorial
review,
we
summarize
latest
advances
area,
aiming
at
providing
clear
overview
on
reaction
design,
mechanistic
scenarios
potential
future
developments.
ACS Sustainable Chemistry & Engineering,
Journal Year:
2021,
Volume and Issue:
9(27), P. 8895 - 8918
Published: June 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.
Chemistry - A European Journal,
Journal Year:
2020,
Volume and Issue:
27(4), P. 1270 - 1281
Published: Aug. 5, 2020
Abstract
Among
the
available
methods
to
increase
molecular
complexity,
sigmatropic
rearrangements
occupy
a
distinct
position
in
organic
synthesis.
Despite
being
known
for
over
century
rearrangement
reactions
of
ylides
via
carbene
transfer
reaction
have
only
recently
come
age.
Most
ylide
mediated
processes
involve
rupture
σ‐bond
and
formation
new
bond
between
π‐bond
negatively
charged
atom
followed
by
simultaneous
redistribution
π‐electrons.
This
minireview
describes
advances
this
research
area
made
recent
years,
which
now
opens
up
metal‐catalyzed
enantioselective
reactions,
metal‐free
photochemical
novel
pathways
that
can
be
accessed
intermediates.
Chemical Reviews,
Journal Year:
2024,
Volume and Issue:
124(11), P. 7214 - 7261
Published: May 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.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(48), P. 7346 - 7360
Published: Jan. 1, 2023
This
article
discusses
the
photochemistry
of
several
diazo
compounds
undergoing
visible
light-mediated
photolysis
to
generate
free
carbenes
(or
other
highly
reactive
intermediates),
which
can
be
sequentially
trapped
by
different
reacting
partners.
Chemistry - A European Journal,
Journal Year:
2019,
Volume and Issue:
26(12), P. 2586 - 2591
Published: Dec. 11, 2019
The
photolysis
of
diazoalkanes
is
a
timely
strategy
to
conduct
carbene-transfer
reactions
under
mild
and
metal-free
reaction
conditions,
has
developed
as
an
important
alternative
conventional
metal-catalyzed
reactions.
One
the
major
limitations
lies
within
rapidly
occurring
side
carbene
intermediate
with
remaining
diazoalkane
molecules
that
result
in
use
excess
partner
thus
impacts
on
efficiency.
Herein,
we
describe
protocol
takes
advantage
situ
generation
donor-acceptor
by
Bamford-Stevens
reaction.
Following
this
strategy,
concentration
can
be
minimized
reduce
unwanted
now
photochemical
transfer
stoichiometric
conditions.
We
have
explored
approach
C-H
N-H
functionalization
cyclopropanation
N-heterocycles
could
demonstrate
applicability
method
51
examples.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(17), P. 6951 - 6955
Published: Aug. 12, 2021
A
green
and
sustainable
oxime
ether
formation
method
via
the
visible-light-promoted
O–H
functionalization
of
oximes
with
diazo
esters
is
described.
The
reaction
occurs
under
very
mild
conditions
(catalyst-
additive-free)
a
high
yield
functional
group
tolerance.
When
was
performed
cyclic
as
solvent
(e.g.,
THF,
1,4-dioxane,
tetrahydropyran,
ect.),
an
interesting
photochemical
three-component
product
obtained
in
good
yields.
Green Chemistry,
Journal Year:
2022,
Volume and Issue:
24(12), P. 4915 - 4920
Published: Jan. 1, 2022
A
convenient
and
eco-friendly
visible-light
promoted
multicomponent
protocol
has
been
developed
for
the
synthesis
of
S
-alkyl
phosphorothioates
by
using
elemental
sulfur
as
cheap
odorless
source.
