Organic Letters,
Год журнала:
2020,
Номер
22(21), С. 8500 - 8504
Опубликована: Окт. 12, 2020
An
efficient
radical
transannulation
reaction
of
pyridotriazoles
with
isothiocyanates
and
xanthate
esters
was
developed.
This
method
features
conversion
into
two
N-fused
heterocyclic
aromatic
systems—imino-thiazolopyridines
oxo-thiazolopyridine
derivatives—via
one-step
Co(II)-catalyzed
proceeding
via
a
mechanism.
The
synthetic
usefulness
the
developed
illustrated
in
synthesis
amino
acid
derivatives
further
transformations
obtained
products.
Organic Letters,
Год журнала:
2023,
Номер
25(1), С. 169 - 173
Опубликована: Янв. 5, 2023
Cyclopropane-fused
lactones
are
highly
desirable
in
drug
and
natural
products
synthesis.
Herein,
we
report
on
a
photochemical,
chemoselective
reaction
of
aryldiazoacetates
with
allylic
alcohols
that
furnishes
cyclopropane-fused
lactone
skeletons
efficiently
one
step.
The
diastereoselectivity
the
protocol
was
precisely
controlled,
cyclopropanation
via
free
carbene
intermediate
followed
by
transesterification
constitutes
series
bicyclic
high
yield
without
formation
ether
byproducts
typical
O–H
insertion
reactions.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(32), С. 22140 - 22144
Опубликована: Авг. 5, 2024
We
present
here
a
catalytic
method
based
on
low-valent
Bi
complex
capable
of
cyclopropanation
double
bonds
under
blue
LED
irradiation.
The
catalysis
features
various
unusual
Bi-based
organometallic
steps,
namely,
(1)
two-electron
inner
sphere
oxidative
addition
Bi(I)
to
CH2I2,
(2)
light-induced
homolysis
the
Bi(III)–CH2I
bond,
(3)
subsequent
iodine
abstraction-ring-closing,
and
(4)
reduction
Bi(III)
with
an
external
reducing
agent
close
cycle.
Stoichiometric
experiments
support
proposed
mechanism.
This
protocol
represents
unique
example
reductive
photocatalytic
process
bismuth
radical
catalysis.
Chemical Communications,
Год журнала:
2019,
Номер
56(4), С. 599 - 602
Опубликована: Дек. 3, 2019
Herein,
we
report
on
a
photochemical
three-component
reaction
of
aryldiazoacetates
with
NFSI
and
cyclic
ethers.
This
method
allows
the
introduction
both
fluorine
short
ether
sidechain
using
1,4-dioxane
as
solvent
in
high
yields
via
an
ylide
pathway
demonstrated
by
DFT
calculations
(26
examples,
up
to
99%
yield).
Asian Journal of Organic Chemistry,
Год журнала:
2020,
Номер
9(8), С. 1133 - 1143
Опубликована: Июнь 16, 2020
Abstract
Pyridinium
ylide
is
a
versatile
building
block
in
synthetic
organic
chemistry,
especially
the
synthesis
of
N
‐heterocycles.
In
this
minireview,
we
have
summarized
advances
[3+2]‐cycloaddition
catalytically
generated
pyridinium
for
indolizines
(since
1970s).
Accordingly,
discussed
article
situ
from
carbene
precursors
and
‐heteroarenes
under
catalytic
conditions,
including
photocatalysis/thermocatalysis,
metal‐catalysis.
The
metal‐catalyzed
version
main
focus,
which
classified
based
on
type
dipolarophiles,
alkyne
alkene,
each
class
further
subdivided
according
to
metal
catalysts
used
these
reactions.
analogous
vinyl
with
pyridines,
formation
other
or
different
‐heteroarenes,
been
also
included
herein
separately.
Organic Letters,
Год журнала:
2020,
Номер
22(21), С. 8500 - 8504
Опубликована: Окт. 12, 2020
An
efficient
radical
transannulation
reaction
of
pyridotriazoles
with
isothiocyanates
and
xanthate
esters
was
developed.
This
method
features
conversion
into
two
N-fused
heterocyclic
aromatic
systems—imino-thiazolopyridines
oxo-thiazolopyridine
derivatives—via
one-step
Co(II)-catalyzed
proceeding
via
a
mechanism.
The
synthetic
usefulness
the
developed
illustrated
in
synthesis
amino
acid
derivatives
further
transformations
obtained
products.
