Organic Letters,
Год журнала:
2024,
Номер
26(1), С. 390 - 395
Опубликована: Янв. 2, 2024
Molecules
containing
heteroatoms,
such
as
Se
and
S,
play
an
indispensable
role
in
the
discovery
design
of
pharmaceuticals,
whereas
has
been
less
studied.
Here,
we
described
a
photoredox
strategy
to
synthesize
C-benzoselenazolyl
(Bs)
glycosides
from
2-isocyanoaryl
selenoethers
glycosyl
bromides.
This
reaction
was
carried
out
under
mild
conditions
with
high
efficiency.
C-Benzothiazolyl
(Bt)
could
also
be
synthesized
thioethers
using
this
strategy.
method
can
access
novel
seleno/thiosugars,
which
will
benefit
Se/S-containing
drug
discovery.
Green Chemistry,
Год журнала:
2019,
Номер
21(17), С. 4706 - 4711
Опубликована: Янв. 1, 2019
A
direct
electrochemical
oxidative
cyclization
of
activated
alkynes
with
diselenides
or
disulfides
toward
functionalized
coumarins
and
quinolinones
has
been
developed.
ACS Catalysis,
Год журнала:
2020,
Номер
10(21), С. 12636 - 12641
Опубликована: Окт. 16, 2020
Electron
donor–acceptor
(EDA)
complexes
can
controllably
generate
radicals
under
mild
conditions
through
selective
photoexcitation
events.
However,
unproductive
reactivity
from
fast
deactivation
of
the
photoexcited
back
electron
transfer
has
slowed
development
EDA
in
synthetic
methodology.
Here,
we
disclose
study
derived
2-methoxynaphthalene
donor
and
acylated
ethyl
isonicotinate
N-oxide
acceptor
that
undergo
a
N–O
bond
fragmentation
event
upon
photoexcitation.
This
reaction
design
not
only
overcomes
limitations
but
also
enables
regeneration
species,
representing
rare
example
photochemistry
catalytic
regime.
The
utility
is
demonstrated
visible
light-driven
radical
trifluoromethylation
Minisci
alkylation
reactions.
scalability
complex-promoted
evidenced
by
successful
multigram-scale
methyl
N-Boc
pyrrole-2-carboxylate
continuous
flow
manifold.
The Journal of Organic Chemistry,
Год журнала:
2019,
Номер
84(16), С. 10160 - 10171
Опубликована: Июль 22, 2019
A
simple
metal–ligand
cooperative
approach
for
the
dehydrogenative
functionalization
of
alcohols
to
various
substituted
quinolines
and
quinazolin-4(3H)-ones
under
relatively
mild
reaction
conditions
(≤90
°C)
is
reported.
Simple
easy-to-prepare
air-stable
Cu(II)
complexes
featuring
redox-active
azo-aromatic
scaffolds,
2-arylazo-(1,10-phenanthroline)
(L1,2),
are
used
as
catalyst.
wide
variety
were
synthesized
in
moderate
good
isolated
yields
via
coupling
reactions
inexpensive
easily
available
starting
materials
aerobic
conditions.
few
control
experiments
deuterium
labeling
studies
carried
out
understand
mechanism
reactions,
which
indicate
that
both
copper
coordinated
ligand
participate
a
manner
during
catalytic
cycle.
Advanced Synthesis & Catalysis,
Год журнала:
2019,
Номер
361(22), С. 5176 - 5181
Опубликована: Сен. 26, 2019
Abstract
A
metal‐free
visible‐light‐induced
cyclization
procedure
was
developed
for
the
rapid
synthesis
of
perfluoroalkyl‐substituted
benzimidazo[2,1‐
a
]isoquinolin‐6(5
H
)‐ones
and
indolo[2,1‐
under
mild
reaction
conditions.
In
this
procedure,
formation
electron‐donor‐acceptor
(EDA)
complex
is
critical
visible‐light
promoted
process
to
avoid
utilization
external
photocatalysts.
magnified
image
Organic Letters,
Год журнала:
2019,
Номер
21(13), С. 5341 - 5345
Опубликована: Июнь 21, 2019
Two
efficient
continuous
flow
iodoperfluoroalkylation
methods
are
described:
using
0.05
mol
%
perylene
diimide
(PDI)
photocatalyst
under
450
nm
irradiation
or
substoichiometric
triethylamine
405
irradiation.
These
enable
dramatically
elevated
productivity
versus
batch
processes.
The
triethylamine-mediated
method
is
explored
mechanistically
and
in
substrate
scope.
gram-scale
synthesis
of
an
active
pharmaceutical
ingredient
side
chain
also
reported
flow,
via
a
photochemical
followed
by
hydrogenolysis.
Organic Letters,
Год журнала:
2019,
Номер
21(19), С. 7823 - 7827
Опубликована: Сен. 18, 2019
An
efficient
metal-free,
photomediated
iodo
perfluoroalkylation
under
mild
conditions
was
developed.
Using
catalytic
amounts
(10
mol
%)
of
phosphines
and
blue
light
irradiation,
various
olefins
are
transformed
into
the
corresponding
addition
products
within
short
reaction
times.
For
this
purpose,
a
modular
convenient
3D
printed
photoreactor
constructed,
which
is
presented
as
an
open
source
model.
The
presumably
proceeds
upon
generation
perfluoroalkyl
radicals,
formed
by
catalyst-induced
absorption
enhancement.
ChemSusChem,
Год журнала:
2020,
Номер
13(8), С. 2053 - 2059
Опубликована: Фев. 3, 2020
A
novel
and
green
route
has
been
developed
for
the
electrochemical
synthesis
of
spiro[4.5]trienones
through
radical-initiated
dearomative
spirocyclization
alkynes
with
diselenides.
This
metal-free
oxidant-free
electrosynthesis
reaction
was
performed
in
an
undivided
cell
under
mild
conditions.
variety
selenation
products
were
prepared
moderate-to-good
yields,
showing
a
broad
scope
functional
group
tolerance.
Moreover,
continuous-flow
system
combined
possesses
potential
to
achieve
scaled-up
reactions,
overcoming
low
efficiency
conventional
reactions.
Chemical Communications,
Год журнала:
2020,
Номер
56(12), С. 1815 - 1818
Опубликована: Янв. 1, 2020
The
first
example
of
visible
light
promoted
fluoroalkylation
reactions
initiated
via
noncovalent
interactions
between
acetone
and
fluoroalkyl
iodides
is
presented.
reaction
system
features
synthetic
simplicity,
mild
conditions
without
any
photoredox
catalyst,
high
functional
group
tolerance.
A
wide
range
substrate
scopes
such
as
alkenes,
alkynes
(hetero)arenes
were
all
compatible
with
the
system.
