Organic Letters,
Год журнала:
2019,
Номер
21(23), С. 9763 - 9768
Опубликована: Ноя. 20, 2019
Catalytic
enantioselective
chemical
reactions
involving
highly
reactive
radical
species
remain
largely
unexplored.
We
report
herein
for
the
first
time
a
novel
ring-opening
cyanation
of
redox-active
oxime
esters
by
dual
photoreodox
and
copper
catalysis.
This
mild
protocol
shows
good
functional
group
tolerance
broad
substrate
scope,
producing
wide
range
optically
active
alkyl
dinitriles
with
high
yields
excellent
enantioselectivities,
which
are
difficult
to
access
traditionally.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(4), С. 917 - 922
Опубликована: Янв. 1, 2022
The
synthesis
of
β-azidosulfones
starting
from
alkenes,
cycloketone
oxime
esters,
trimethylsilyl
azide
and
a
sulfur
dioxide
surrogate
DABCO·(SO
2
)
under
iron
catalysis
is
developed.
ACS Catalysis,
Год журнала:
2025,
Номер
15(3), С. 1854 - 1941
Опубликована: Янв. 17, 2025
Over
the
past
decade,
visible-light-mediated
energy-transfer
(EnT)
catalysis,
particularly
triplet–triplet
(TTEnT)
has
emerged
as
a
mild
and
environmentally
friendly
approach
for
diverse
organic
synthetic
transformations.
In
contrast
to
photoredox
which
typically
requires
sacrificial
electron
donors
or
acceptors
complete
catalytic
cycle,
EnT
photocatalysis
generally
proceeds
with
high
atom
economy
while
minimizing
generation
of
wasteful
byproducts.
Furthermore,
successful
catalysis
is
contingent
upon
precise
control
redox
potentials
both
photocatalysts
substrates,
strategies
are
primarily
influenced
by
triplet
energy
compatibility
between
these
entities.
Considering
growing
importance
photocatalysis,
well
hydrofunctionalization
difunctionalization
reactions
in
synthesis,
this
review
systematically
summarizes
significant
advancements
EnT-enabled
unsaturated
compounds
via
sigma-bond
homolysis
over
decade.
Special
emphasis
placed
on
elucidating
substrate
scopes
mechanistic
scenarios.
Additionally,
discusses
versatile
applications
methodologies
addresses
current
challenges
opportunities
within
evolving
research
field.
This
structured
into
six
main
categories
based
different
types
sigma-bonds
undergoing
homolysis.
These
include
transformations
mediated
1)
N–O
bond
oxime
esters
other
N,O-radical
precursors;
2)
N–S
N-sulfonyl
imines
N,S-radical
3)
chalcogen–chalcogen
disulfides
oxy/thio/selenosulfonates;
4)
C–S
tri/difluoromethylated
sulfinates,
acetylenic
triflones,
arylsulfonium
salts;
5)
C–X
(X
=
halogen)
halides;
6)
acceptors.
Through
providing
theoretical
backgrounds
along
comprehensive
overview
currently
employed
acceptors,
photosensitizers,
contemporary
EnT-induced
compounds,
aims
serve
an
invaluable
resource
future
innovations
rapidly
Organic Letters,
Год журнала:
2019,
Номер
21(23), С. 9763 - 9768
Опубликована: Ноя. 20, 2019
Catalytic
enantioselective
chemical
reactions
involving
highly
reactive
radical
species
remain
largely
unexplored.
We
report
herein
for
the
first
time
a
novel
ring-opening
cyanation
of
redox-active
oxime
esters
by
dual
photoreodox
and
copper
catalysis.
This
mild
protocol
shows
good
functional
group
tolerance
broad
substrate
scope,
producing
wide
range
optically
active
alkyl
dinitriles
with
high
yields
excellent
enantioselectivities,
which
are
difficult
to
access
traditionally.
