Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(23), P. 9292 - 9296
Published: Nov. 19, 2021
Two
new
visible-light-mediated
strategies
are
described
starting
from
aryldiazoacetates.
The
first
approach
describes
their
reaction
with
azides
to
afford
the
corresponding
imines,
and
then
aryldiazoketones
produces
alkyl
2-carboxylate-2,3,3-trisubstituted
β-lactams.
second
sulfoxides
sulfoxonium
ylides,
followed
by
produce
5-alkoxy-2,2,4-trisubstituted
furan-3(2H)-ones.
These
protocols
take
advantage
of
photolysis
aryldiazoacetates
photochemically
promoted
Wolff
rearrangement
aryldiazoketones.
Chemical Science,
Journal Year:
2022,
Volume and Issue:
13(42), P. 12290 - 12308
Published: Jan. 1, 2022
Catalytic
asymmetric
sigmatropic
rearrangements
induced
by
chiral
metal
catalysis
have
been
intensively
explored.
This
review
summarizes
recent
significant
advances,
mainly
involving
[3,3],
[2,3]
and
[1,3]-rearrangements.
Chemical Society Reviews,
Journal Year:
2022,
Volume and Issue:
51(14), P. 5842 - 5877
Published: Jan. 1, 2022
Transition
metal-catalysed
carbene-
and
nitrene
transfer
to
the
C1-building
blocks
carbon
monoxide
isocyanides
provides
heteroallenes
(i.e.
ketenes,
isocyanates,
ketenimines
carbodiimides).
These
are
versatile
reactive
compounds
allowing
in
situ
transformation
towards
numerous
functional
groups
organic
compounds,
including
heterocycles.
Both
one-pot
tandem
processes
have
been
developed
providing
valuable
synthetic
methods
for
chemistry
toolbox.
This
review
discusses
all
known
transition
reactions
of
hereby
obtained,
with
a
special
focus
on
general
mechanistic
considerations.
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(6), P. 3279 - 3285
Published: Feb. 25, 2022
A
visible
light-driven
photoredox-catalyzed
and
copper(II)-assisted
three-component
radical
addition/hydroxylation
reaction
of
alkenes,
sulfur
ylides,
water
is
reported.
This
process
shows
broad
substrate
scope
high
functional
group
tolerance,
with
respect
to
both
readily
available
ylides
providing
high-yielding
practical
access
valuable
γ-hydroxy
carbonyl
compounds.
Key
the
success
controlled
generation
α-carbonyl
carbon
radicals
from
via
sulfonium
salts
by
a
visible-light-driven
proton-coupled
electron
transfer
(PCET)
strategy
in
mixture
2,2,2-trifluoroethanol/CH2Cl2.
Addition
Cu(TFA)2·H2O
helps
accelerate
radical-cation
crossover
improve
efficiency.
Mechanistic
studies
suggest
that
hydroxy
moiety
products
stems
water.
study
also
builds
up
platform
for
further
investigation
into
synthetic
chemistry
ylides.
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.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(10)
Published: Jan. 14, 2023
[2,3]-Sigmatropic
rearrangement
reaction
involving
sulfonium
ylide
(Doyle-Kirmse
reaction)
generated
from
metal
carbenes
represents
one
of
the
powerful
methods
for
construction
C(sp3
)-S
and
C-C
bonds.
Although
significant
advances
have
been
achieved,
asymmetric
versions
via
generation
ylides
rarely
reported
to
date,
they
so
far
limited
diazo
compounds
as
carbene
precursors.
Here,
we
describe
a
copper-catalyzed
enantioselective
Doyle-Kirmse
azide-ynamide
cyclization,
leading
practical
divergent
assembly
an
array
chiral
[1,4]thiazino[3,2-b]indoles
bearing
quaternary
carbon
stereocenter
in
generally
moderate
excellent
yields
enantioselectivities.
Importantly,
this
protocol
unique
catalytic
non-diazo
approach
unprecedented
[2,3]-sigmatropic
α-imino
carbenes.
Chemical Society Reviews,
Journal Year:
2024,
Volume and Issue:
53(10), P. 4926 - 4975
Published: Jan. 1, 2024
In
search
for
the
perfect
wave(length).
This
review
is
dedicated
to
recent
efforts
in
development
of
visible
light
driven
photochemical
strategies
occurring
coloured
organic
compounds.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 30, 2025
The
complicated
mechanism
makes
the
regiodivergent
rearrangement
of
ammonium
ylide
seem
to
be
out
reach.
Herein,
we
reported
a
gramine
well
controlled
by
substituents.
Density
functional
theory
studies
reveal
that
with
more
steric
hindrance
substituent
2-diazo-2-arylacetate
goes
through
stepwise
yield
both
kinetically
and
thermodynamically
preferred
[1,2]-rearrangement
product.
In
contrast,
less
ethyl
diazoacetate
concerted
generate
[2,3]-rearrangement
product,
which
is
favored
as
result
release
ring
strain
in
transition
state.
This
study
would
open
up
avenues
grasp
ylide,
will
promote
application
skeletal
editing
synthesis
complex
natural
products.
Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(21), P. 5982 - 5987
Published: Jan. 1, 2021
A
green
and
efficient
route
for
the
synthesis
of
trisubstituted
hydroxylamines
from
β-keto
ester,
2-nitrosopyridine
aryldiazoacetates
has
been
reported.
This
multicomponent
reaction
occurred
under
mild
conditions
without
catalysts
or
additives.
