The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(11), P. 7245 - 7255
Published: May 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.
Advanced Synthesis & Catalysis,
Journal Year:
2020,
Volume and Issue:
363(1), P. 62 - 119
Published: Oct. 31, 2020
Abstract
The
use
of
clean
and
renewable
light
sources
is
increasingly
common
in
organic
synthesis
due
to
its
safety,
practicality
economy.
Recently,
photoredox
catalysis
has
shown
great
application
values
transformations
because
advantages
environmentally
friendly
abundant
resources.
Indoles
their
derivatives
(indolines,
oxindoles
isatins)
are
the
core
skeletons
some
important
compounds
widely‐present
various
natural
products
pharmaceuticals
with
different
biological
activities.
Therefore,
research
on
modification
indoles
particularly
for
chemists
pharmacologists.
This
review
summarizes
effects
photocatalysis
indole
recent
decades.
These
accomplished
by
using
metal
photocatalysts
(
i.
e
.,
Ir,
Ru,
Ni,
Cu,
Fe,
Au,
Rh,
TiO
2
,
etc.)
or
non‐metallic
Rose
Bengal,
Eosin
Y,
quinones,
naphthols,
N‐heterocyclic
carbenes,
carbazoles,
pyrylium
salts,
etc.),
without
need
photocatalysts.
detailed
mechanisms
these
photo‐catalyzed/promoted
reactions
also
highlighted
deeply.
And
we
hope
this
will
be
helpful
researchers
interested
promising
field
photocatalyzed
transformations.
magnified
image
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(13), P. 2515 - 2519
Published: March 30, 2022
An
efficient
three-component
radical
iodosulfonylative
cyclization
of
enynes
is
described.
The
visible-light
irradiation
iodoform
with
sulfinates
enables
sulfonyl
generation
under
catalyst-
and
oxidant-free
conditions
triggers
the
addition,
iodination
cascade
reactions,
giving
various
vinyl
iodide
containing
sulfones
in
moderate
to
good
yields.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(11), P. 7401 - 7424
Published: May 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.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(22), P. 5735 - 5745
Published: Jan. 1, 2023
During
the
past
decade,
photo-
and
electrochemical
reactions
proceeding
via
single-electron-transfer
(SET)
triggered
radical
pathways
have
emerged
as
an
indispensable
strategy
for
efficient
formation
of
chemical
bonds.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(11), P. 7245 - 7255
Published: May 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.
