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:
2024,
Volume and Issue:
26(12), P. 2511 - 2516
Published: March 20, 2024
This
work
demonstrates
the
synthesis
of
a
variety
perfluoroalkyl
heterocycles
via
visible-light-driven
radical-polar
crossover
cyclization
strategy.
In
this
process,
single-electron
reduction/SNV-type/cyclization
sequences
follow
radical
addition
reaction
diazoester,
which
differs
from
current
role
diazoesters
as
precursors/acceptors.
transformation
excellent
functional
group
compatibility
and
allows
for
modification
many
bioactive
molecules
with
diazoesters.
Such
could
represent
novel
approach
to
photochemical
diazo
compounds.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
27(2), P. 709 - 714
Published: Jan. 7, 2025
Herein,
we
present
a
visible-light-induced
protocol
for
the
synthesis
of
highly
functionalized
oxo-bridged
oxocine
skeletons.
This
method
generates
carbenes
via
ortho-acyl
diazo
compounds,
which
are
rapidly
intercepted
by
oxygen
atom
an
intermolecular
acyl
group
to
form
cyclic
1,3-dipole.
The
in
situ
generated
reactive
1,3-dipole
undergoes
facile
formal
[4
+
3]
cycloaddition
with
alkenyl
pyrazolinone,
yielding
[4.2.1]-oxo-bridged
compounds.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(8), P. 2654 - 2657
Published: March 29, 2019
A
first
example
of
low-energy
blue-light-mediated
formal
Doyle–Kirmse
reaction
for
gem-difluoroallylation
aryl
diazoesters
has
been
developed.
variety
highly
functionalized
gem-difluoroallyl
containing
esters
bearing
transformable
sulfur
and
bromine
groups
were
efficiently
assembled
with
broad
substrate
scope
under
mild,
catalyst-free,
additive-free
conditions.
The
represents
a
practical
environmentally
friendly
approach
C–CF2
bond
formation
based
on
rearrangement
strategy,
which
will
find
potential
applications
among
drug
discovery
development.
Chemical Science,
Journal Year:
2019,
Volume and Issue:
10(36), P. 8399 - 8404
Published: Jan. 1, 2019
A
highly
efficient
and
practical
method
for
incorporation
of
the
arylmethylpyridyl
moiety
into
diverse
molecules
has
been
developed.
This
features
transition
metal-free
light-induced
room
temperature
transformation
pyridotriazoles
pyridyl
carbenes,
which
are
capable
smooth
arylation,
X-H
insertion,
cyclopropanation
reactions.
The
synthetic
usefulness
developed
was
illustrated
in
a
facile
synthesis
biologically
active
molecules.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(21), P. 8814 - 8818
Published: Oct. 16, 2019
Cyclopropanation
reactions
of
carbenes
with
arenes
provide
a
straightforward
pathway
to
norcaradienes
or
cycloheptatrienes.
This
reaction
normally
requires
harsh
conditions
transition-metal
catalysts.
In
this
report,
we
describe
the
metal-free
visible-light
photolysis
aryl
diazoacetates
in
aromatic
solvents,
which
provides
access
norcaradiene
ring
system
highly
regio-
and
stereoselective
manner.
The
mild
approach
also
allow
chemoselective
cyclopropanation
substituted
without
competing
C-H
functionalization
reactions.
Chemical Science,
Journal Year:
2019,
Volume and Issue:
10(43), P. 10129 - 10134
Published: Jan. 1, 2019
We
have
shown
light
mediated
ring-expansion
reactions
of
4-membered
ring
heterocycles.
The
reaction
proceeds
via
a
diradical
mechanism
and
bond
length
play
key
role
in
the
stereodetermining
step.
Advanced Synthesis & Catalysis,
Journal Year:
2020,
Volume and Issue:
362(10), P. 1927 - 1946
Published: April 8, 2020
Abstract
Over
fifty
years
ago,
the
1,2‐rearrangement
of
acylsilanes
was
first
described
by
Adrian
Brook
and
co‐workers.
This
rearrangement
(now
termed
rearrangement)
yields
reactive
silicon‐based
singlet
nucleophilic
carbene
(SNC)
intermediates
that
participate
in
a
variety
chemical
transformations
including
1,2‐carbonyl
addition,
1,4‐addition
to
electron‐deficient
unsaturated
bonds
insertion
into
C−H
O−H
bonds.
review
aims
cover
historical
literature
recent
advances
with
regard
these
valuable
reagents
highlight
additional
aspects
related
intriguing
reactivity
both
oxocarbenium
intermediates.
magnified
image
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
59(14), P. 5572 - 5576
Published: Dec. 30, 2019
Abstract
A
palladium
catalyzed
C−H
functionalization
and
consecutive
β‐fluoride
elimination
reaction
between
indole
heterocycles
fluorinated
diazoalkanes
is
reported.
This
approach
provides
for
the
first
time
a
facile
method
rapid
synthesis
of
gem‐difluoro
olefins
using
under
mild
conditions.
Cyclopropanation
products
were
obtained
when
N‐arylated
rather
than
N‐alkylated
indoles
applied
in
this
reaction.
Mechanistic
studies
reveal
importance
step
transformation.
presents
new
concept
simple
direct
transfer
1‐aryl‐(2,2‐difluorovinyl)
group
to
access
olefins.
The Journal of Organic Chemistry,
Journal Year:
2020,
Volume and Issue:
85(17), P. 11030 - 11046
Published: Aug. 5, 2020
The
high
demand
for
new
and
efficient
routes
toward
synthesis
of
nitrogen-containing
heterocyclic
scaffolds
has
inspired
organic
chemists
to
discover
several
methodologies
over
recent
years.
This
Perspective
highlights
one
standout
approach,
which
involves
the
use
pyridotriazoles
related
compounds
in
denitrogenative
transformations.
Readily
available
undergo
ring–chain
isomerization
produce
uniquely
reactive
α-diazoimines.
Such
reactivity,
enabled
by
metal
catalysts,
additives,
or
visible-light
irradiation,
can
be
applied
transannulation,
insertion,
cyclopropanation,
many
other
