Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(8), С. 2148 - 2156
Опубликована: Фев. 25, 2021
Abstract
Herein,
we
report
the
[Bis(trifluoroacetoxy)iodo]benzene
mediated
C−H
bond
arylselenylation
of
4
H
‐Pyrido‐[1,2‐
a
]‐Pyrimidin‐4‐ones
using
readily
available
organodiselenides.
This
methodology
is
scalable
and
permits
for
generation
broad
spectrum
functionally
structurally
diverse
selenoether
derivatives
in
very
promising
yields
(up
to
98%).
Notably,
this
protocol
proceeds
at
ambient
conditions
absence
metal.
The
application
facile
synthesis
ArSe
substituted
5
‐thiazolo‐pyrido[3,2‐
]pyrimidin‐4‐ones
also
demonstrated.
magnified
image
The Chemical Record,
Год журнала:
2021,
Номер
21(10), С. 2739 - 2761
Опубликована: Март 3, 2021
Organoselenium
compounds
constitute
an
important
class
of
substances
with
applications
in
the
biological,
medicinal
and
material
sciences
as
well
modern
organic
synthesis,
attracting
considerable
attention
from
scientific
community.
Therefore,
construction
C-Se
bond
via
facile,
efficient
sustainable
strategies
to
access
complex
scaffolds
simple
substrates
are
appealing
hot
topic.
Visible
light
can
be
regarded
alternative
source
energy
is
associated
environmentally-friendly
processes.
Recently,
use
visible-light
mediated
seleno-functionalization
has
emerged
ideal
powerful
route
obtain
high-value
selenylated
products,
diminished
cost
waste.
This
approach,
involving
photo-excited
substrates/catalyst
single-electron
transfer
(SET)
between
presence
visible
been
successfully
used
versatile
direct
insertion
organoselenium
moieties
activated
unactivated
C(sp3
)-H,
C(sp2
C(sp)-H
bonds
C-heteroatom
bonds.
In
most
cases,
ease
operation
accessibility
(LEDs
or
commercial
CFL
bulbs)
makes
this
approach
more
attractive
than
traditional
strategies.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(10), С. 2815 - 2820
Опубликована: Янв. 1, 2022
A
regio-
and
stereoselective
electrochemical
approach
for
the
selenoalkylation
of
alkynes
with
1,3-dicarbonyl
compounds
diselenides
has
been
developed.
Molecules,
Год журнала:
2022,
Номер
27(5), С. 1597 - 1597
Опубликована: Фев. 28, 2022
Organoselenium
compounds
have
been
successfully
applied
in
biological,
medicinal
and
material
sciences,
as
well
a
powerful
tool
for
modern
organic
synthesis,
attracting
the
attention
of
scientific
community.
This
great
success
is
mainly
due
to
breaking
paradigm
demonstrated
by
innumerous
works,
that
selenium
were
toxic
would
potential
impact
on
environment.
In
this
update
review,
we
highlight
relevance
these
several
fields
research
possibility
synthesize
them
through
more
environmentally
sustainable
methodologies,
involving
catalytic
processes,
flow
chemistry,
electrosynthesis,
use
alternative
energy
sources,
including
mechanochemical,
photochemistry,
sonochemical
microwave
irradiation.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(2), С. 1230 - 1239
Опубликована: Янв. 7, 2022
Herein,
we
report
an
efficient
methodology
for
the
synthesis
of
alkyl,
benzyl,
and
phenyl
selenoethers
aminopyrazoles
aminouracils
by
C(sp2)-H
functionalization
in
presence
visible
light
Rose
Bengal
as
organophotocatalyst.
The
reaction
amino
pyrazole/iosothiazole/isoxazole
or
uracils
with
0.5
equivalent
diphenyl/dibenzyl/diethyl
diselenides
acetonitrile
medium
a
catalytic
amount
provided
corresponding
phenyl,
ethyl
good
to
very
yields.
We
have
also
utilized
some
selenylated
preparation
pyrazole-fused
dihydropyrimidines
tethered
arylselenoethers
catalyst-free
one-pot
three-component
reaction.
notable
features
this
are
metal-free
conditions,
yields,
use
organic
photocatalyst,
wide
substrate
scope;
it
is
applicable
gram-scale
provides
medicinally
important
heterocycles
such
amio-pyrazole,
isoxazole,
isothiazole,
uracils.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7401 - 7424
Опубликована: Май 12, 2023
Herein,
we
report
a
blue-light-driven
amination
of
C(sp2)-H
bond
naphthoquinones
and
quinones
with
the
N-H
primary
secondary
amines
for
synthesis
2-amino-naphthoquinones
2-amino-quinones.
The
coupling
wide
array
aliphatic,
aromatic,
chiral,
primary,
having
electron
donating
(-CH3,
-OCH3,
-SCH3),
withdrawing
(-F,
-Cl,
-Br,
-I),
CO2H,
-OH,
-NH2
groups
acidic
protons
selectively
occurred
to
afford
C-N
coupled
in
60-99%
yields
hydrogen
gas
as
byproduct
methanol
solvent
without
using
any
additional
reagents,
additives,
oxidant
under
blue
light
irradiation.
Mechanistic
insight
by
DFT
computation,
controlled
experiments,
kinetic
isotopic
effect,
substitution
effect
substrates
suggest
that
reaction
proceeds
radical
pathway
which
naphthoquinone
forms
highly
oxidizing
naphthoquinonyl
biradical
upon
irradiation
(457
nm).
Consequently,
transfer
from
electron-rich
amine
an
leads
anion
aminyl
cation,
followed
proton
delocalization
leading
carbon-centered
radical.
cross-coupling
nitrogen
radicals
bond,
subsequent
elimination
(which
was
also
confirmed
GC-TCD),
affording
2-amino-1,4-naphthoquinone
metal-,
reagent-,
base-,
oxidant-free
conditions.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7245 - 7255
Опубликована: Май 23, 2023
A
cascade
selenylation/cyclization
of
dienes
with
diselenides
has
been
realized
under
visible-light
irradiation
or
electrolysis
conditions.
Employing
O2
electricity
as
a
"green"
oxidant,
this
protocol
provides
green
and
efficient
method
for
an
array
biologically
important
seleno-benzo[b]azepine
derivatives
in
moderate
to
good
yields.
The
direct
sunlight
gram-scale
reaction
render
the
approach
practical
attractive.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(30), С. 6198 - 6204
Опубликована: Янв. 1, 2024
Reported
herein
is
a
visible-light
induced
selenocyclization
of
2-ethynylanilines
under
ambient
conditions,
with
simple
FeBr
3
as
dual-functional
catalyst.
The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
85(8), С. 5670 - 5682
Опубликована: Апрель 2, 2020
A
visible-light-induced,
catalyst-free
radical
cross-coupling
cyclization
of
diselenides
or
disulfides
with
N-allylbromodifluoroacetamide
has
been
developed.
This
developed
protocol
exhibits
good
functional
group
tolerance
and
affords
a
variety
4-thio-
4-seleno-substituted
3,3-difluoro-γ-lactams
in
moderate
to
yields.
Based
on
control
experiments,
plausible
radical-radical
pathway
is
proposed.
RSC Advances,
Год журнала:
2021,
Номер
11(12), С. 6682 - 6698
Опубликована: Янв. 1, 2021
Aryl
and
heteroaryl
selenides
tellurides
are
found
to
have
broad
applications
in
the
diverse
fields
such
as
medicine,
biology,
materials
science,
pharmaceutical
etc.
thus
their
synthesis
remains
a
challenging
field
for
synthetic
chemists
last
decade.
Although
large
no
of
methodologies
been
developed
based
on
metal
catalyzed
C-Se/Te
coupling,
number
researches
has
focused
developing
catalyst
free
protocols
due
sustainability
recent
times.
This
review
covers
all
developments
decade
under
conditions
by
using
different
sustainable
techniques
e.g.
greener
reagents
solvents,
ball
milling,
visible
light
photocatalysis,
microwave,
ultrasound
