Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(5)
Published: Dec. 9, 2023
Abstract
A
regioselectivity
reversed
three‐component
defluorinative
alkylboration
of
alkenes
with
trifluoromethyls
and
bis(pinacolato)diboron
via
dual
photoredox/copper
catalysis
is
reported.
The
mild
conditions
are
compatible
a
wide
array
nonactivated
trifluoromethyl
aromatics
bearing
electron‐donating
or
electron‐neutral
substituents,
trifluoroacetamides,
various
terminal
internal
alkenes,
enabling
straightforward
access
to
synthetically
valuable
γ
‐
gem
‐difluoroalkyl
boronates
high
efficiency.
Furthermore,
this
protocol
applicable
alkene‐tethered
furnish
‐difluoromethylene‐containing
cyclic
compounds.
Synthetic
applications
preliminary
mechanistic
studies
also
presented.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(5), P. 1016 - 1022
Published: Jan. 25, 2022
Abstract
An
electrochemical
hydroxysulfonylation
of
α‐CF
3
alkenes
was
accomplished
in
this
work.
By
using
easily
available
sodium
sulfinates
as
the
sulfonylating
agents,
a
series
valuable
α‐trifluoromethyl
tertiary
alcohols
were
synthesized
under
mild
and
environmentally
friendly
electrolysis
conditions
moderate
to
good
yields.
The
preliminary
mechanistic
investigation
indicates
that
difunctional
reaction
involves
radical
process
via
sulfonyl
radical.
Gram‐scale
synthesis
shows
significant
potential
application
protocol.
magnified
image
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(32), P. 5946 - 5950
Published: Aug. 4, 2022
A
photocatalytic
three-component
reaction
of
α-trifluoromethyl
alkenes,
electron-rich
and
sodium
sulfinates
for
the
synthesis
gem-difluoroalkenes
in
a
radical/polar
crossover
manner
was
developed.
Due
to
strong
electron-withdrawing
nature
sulfonyl
group,
resultant
can
be
converted
into
various
monofluorocyclopentenes
via
intramolecular
base-mediated
SNV
reactions
one
pot.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(38), P. 7047 - 7051
Published: Sept. 19, 2022
Commercially
available
CF2Br2
has
been
used
as
a
convenient
source
for
the
rapid
and
reliable
incorporation
of
gem-difluorovinyl
motif
into
an
allene
framework
via
N-heterocyclic
carbene
catalyzed
difluoroolefination
1,3-enynes.
The
reaction
proceeds
through
cascade
three-component
radical
relay/elimination
process.
This
protocol
is
distinguished
by
its
mild
conditions,
readily
accessible
starting
materials,
wide
substrate
scope,
ease
late-stage
functionalization,
thus
unlocking
untraditional
strategy
to
construct
new
class
functionalized
allenes.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(12), P. 2026 - 2035
Published: May 22, 2023
Abstract
An
alternative
strategy
for
the
mechanochemical
defluorinative
acylation
of
ortho
‐hydroxyarylenaminones
has
been
developed
to
synthesise
3‐acylchromones
utilizing
CF
3
‐compounds
via
activation
C−F
bound
trifluoromethyl
group
in
presence
ytterbia
(Yb
2
O
).
The
current
protocol
tolerated
a
wide
range
coupling
substrates
access
library
diversely
substituted
under
mechanochemically
induced
domino
cyclisation
mode.
This
is
first
report
deflourinative
transformation
inert
corresponding
carbonyl
functionality
conditions.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(5)
Published: Dec. 9, 2023
Abstract
A
regioselectivity
reversed
three‐component
defluorinative
alkylboration
of
alkenes
with
trifluoromethyls
and
bis(pinacolato)diboron
via
dual
photoredox/copper
catalysis
is
reported.
The
mild
conditions
are
compatible
a
wide
array
nonactivated
trifluoromethyl
aromatics
bearing
electron‐donating
or
electron‐neutral
substituents,
trifluoroacetamides,
various
terminal
internal
alkenes,
enabling
straightforward
access
to
synthetically
valuable
γ
‐
gem
‐difluoroalkyl
boronates
high
efficiency.
Furthermore,
this
protocol
applicable
alkene‐tethered
furnish
‐difluoromethylene‐containing
cyclic
compounds.
Synthetic
applications
preliminary
mechanistic
studies
also
presented.
