European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(42)
Опубликована: Сен. 5, 2023
Abstract
Metal‐free,
visible
light‐induced
difunctionalizations
of
α
‐CF
3
styrenes
with
aryl
diazonium
salts
and
various
hetero
nucleophiles
(ROH,
H
2
O,
N
−
F
)
are
described.
This
concise
protocol
provided
easy
access
to
the
tertiary
alkyl
ethers,
alcohol
fluorides
good
yields
excellent
functional
group
tolerance.
In
addition,
four‐component
“SO
”
insertion
reaction
also
worked
efficiently
produce
,
β
‐sulfonyl
ethers
in
moderate
yields.
A
radical‐polar
crossover
coupling
pathway
was
proposed
for
C−O
bond
formation.
Organic Letters,
Год журнала:
2024,
Номер
26(28), С. 6030 - 6034
Опубликована: Июль 8, 2024
A
photoredox-catalyzed
sequential
decarboxylative/defluorinative
aminoalkylation
of
CF3-alkenes
with
N-arylglycines
is
described.
This
metal-free
and
redox-neutral
protocol
provided
efficient
access
to
the
monofluoroalkenyl-1,5-diamines
in
good
yields
excellent
functional
group
compatibility.
Mechanistic
studies
revealed
that
reaction
proceeds
via
a
radical
pathway
gem-difluoroalkenyl
amine
as
an
intermediate.
Organic Letters,
Год журнала:
2024,
Номер
26(15), С. 3208 - 3212
Опубликована: Апрель 10, 2024
Herein,
we
report
a
catalyst-free
reaction
of
cyclobutanone
oximes
with
chlorophosphines
(R2PCl),
which
forms
fragile
C═N–O–PR2
species
that
undergoes
N–O
homolysis,
fragmentation,
and
radical–radical
coupling,
leading
to
the
formation
cyano-containing
phosphine
oxides
in
good
yields.
The
features
an
situ
activation
for
radical
generation,
R2PCl
plays
dual
role
as
both
activator
reactant.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 22, 2025
We
disclosed
an
organophotoredox-catalyzed
three-component
oxidative
radical-polar
crossover
strategy
for
constructing
1,2-alkylamination
products.
Cycloketone
oxime
derivatives
were
used
as
cyanoalkyl
radical
precursors
and
anilines
the
nucleophiles.
This
facile
protocol
shows
a
good
reaction
yield
broad
substrate
scope.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Июнь 4, 2025
A
facile
and
straightforward
electrochemical
oxidative
azidohydroxylation
diazidation
of
α-CF3
alkenes
with
TMSN3
has
been
achieved.
Significantly,
a
series
densely
functionalized
potentially
medicinally
valuable
β-trifluoromethylated
azido
compounds
were
assembled
under
mild
conditions
using
constant
current
in
an
undivided
cell
without
any
external
oxidants
catalysts.
Notably,
this
protocol
exhibited
broad
scope
functional
group
tolerance
to
deliver
azidohydroxyla-tion
products,
respectively,
by
replacing
the
electrode
solvent.
The
reaction
mechanism
was
also
preliminarily
studied.
Abstract
Transition‐metal‐catalyzed
radical
relay
cross‐coupling
reactions
of
1,3‐dienes
have
recently
emerged
as
one
the
most
powerful
methods
for
construction
structurally
diverse
allylic
compound
in
a
single
chemical
step.
However,
there
still
has
been
limited
success
expanding
substrate
scope
precursors
and
coupling
partners,
well
exploring
catalytic
asymmetric
variants.
Herein,
we
report
copper‐catalyzed
enantioselective
three‐component
1,2‐alkylesterification
using
cycloalkyl
hydroperoxides
carbonyl‐containing
alkyl
sources
carboxylic
acids
O‐nucleophiles
under
mild
redox‐neutral
conditions.
This
protocol
features
broad
good
functional
group
tolerance
with
respect
to
each
component,
providing
practical
access
variety
distally
keto‐functionalized
esters
high
enantioselectivity.
Mechanistic
studies
suggest
involvement
sequential
C−O
this
reaction.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(43), С. 8744 - 8748
Опубликована: Янв. 1, 2023
A
halotrimethylsilane
facilitated
cycloketonization
of
γ
-hydroxyl
ynones
is
detailed
for
one-step
synthesis
polysubstituted
3(2
H
)-furanone
products.
Chemical Communications,
Год журнала:
2024,
Номер
60(40), С. 5334 - 5337
Опубликована: Янв. 1, 2024
A
photoredox-catalyzed
alkylarylation
of
activated
alkenes
via
a
ring-opening/Truce–Smiles
rearrangement
cascade
is
developed.
The
protocol
features
broad
substrate
scope
and
excellent
functional
group
compatibility.
Organic Letters,
Год журнала:
2024,
Номер
26(25), С. 5312 - 5317
Опубликована: Июнь 13, 2024
Cu-catalyzed
asymmetric
construction
of
a
chiral
quaternary
center
bearing
CH3
and
CF3
groups
was
achieved
with
high
to
excellent
enantioselectivity
using
our
originally
developed
ligands.
The
conjugate
addition
Me3Al
β-CF3-substituted
enones
unsaturated
ketoesters
proceeded
efficiently.
use
gives
optically
active
furanones
in
yields
enantioselectivities.
perfluoroalkyl-substituted
enone
does
not
seem
be
favorable
the
present
reaction.
Organic Letters,
Год журнала:
2024,
Номер
26(44), С. 9610 - 9616
Опубликована: Окт. 25, 2024
An
efficient
and
metal-free
approach
for
the
divergent
synthesis
of
2-fluoro-3-aryl-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines
α-trifluoromethyl-β-arylthio
tertiary
alcohols
from
2-mercaptoimidazoles
α-CF3
alkenes
has
been
developed.
The
chemoselectivity
was
well
controlled
by
base
or
light;
a
series
were
afforded
via
base-mediated
sequential
SN2′-
SNV-type
reactions.
Meanwhile,
could
be
selectively
achieved
through
visible-light-driven
electron
donor–acceptor
(EDA)
complex-initiated
radical
cascade
thiolation/hydroxylation
in
absence
base,
transition
metal,
external
photocatalyst.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(11), С. 2501 - 2506
Опубликована: Апрель 17, 2024
Abstract
A
Mn‐electrocatalytic
ring‐opening
azidation
of
tert
‐cyclobutanols
has
been
developed.
The
regioselective
method
is
applicable
for
the
a
diverse
array
cyclobutanols
to
provide
practical
γ
‐azido
ketones
in
23–91%
yields
under
chemical
oxidants‐free
reaction
conditions.
Detailed
mechanistic
studies
suggest
process
Mn‐mediated
alkoxy
radical
generation
followed
by
β
‐scission
form
carbon‐centered
species
possibly
involved
this
transformation.
