We
herein
report
a
photochemical
Truce–Smiles
rearrangement
reaction
of
N-sulfinyl
acrylamides
with
bromodifluoroacetamides
resulting
in
the
synthesis
series
aryl
difluoroglutaramides
moderate
to
good
yields.
The
asymmetric
using
chiral
sulfinamides
produced
quaternary
carbon-centered
glutaramide
products
modest
enantioselectivity.
This
protocol
effectively
complements
previous
methods
involving
N-sulfonyl
acrylamides.
Organic Letters,
Год журнала:
2023,
Номер
25(31), С. 5756 - 5761
Опубликована: Июль 28, 2023
Herein
we
report
a
nickel-catalyzed
regioselective
cross-electrophile
ring
opening
reaction
of
sulfonyl-protected
aziridines
with
trifluoromethyl-substituted
alkenes
as
the
gem-difluoroallylating
agents,
providing
new
and
efficient
entry
to
prepare
gem-difluorobishomoallylic
sulfonamides.
Moreover,
scaffold
6-fluoro-1,2,3,4-tetrahydropyridine
can
be
constructed
starting
from
products
via
NaH-mediated
intramolecular
defluorinative
nucleophilic
vinylic
substitution.
Organic Letters,
Год журнала:
2023,
Номер
25(33), С. 6122 - 6127
Опубликована: Авг. 14, 2023
Herein,
we
describe
a
nickel-catalyzed
asymmetric
dearomative
aryl-difluoroallylation
reaction
of
indoles
with
α-trifluoromethyl
alkenes
as
an
electrophilic
coupling
partner.
The
proceeds
via
cascade
sequence
involving
Heck
cyclization
and
reductive
allylic
defluorination.
A
series
gem-difluoroallyl
substituted
indolines
are
obtained
in
moderate
to
good
yields
(36-77%
yield)
excellent
enantioselectivity
(up
99%
ee).
features
broad
functional
group
tolerance,
scaled-up
synthesis,
late-stage
diversification.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(2), С. 458 - 465
Опубликована: Ноя. 23, 2023
A
visible-light-mediated
selective
difluoroalkylation
of
α-trifluoromethyl
alkenes
with
difluoroalkylating
reagents
was
developed.
This
protocol
allowed
the
formation
gem
-difluoroalkene
difluoroacetates
and
trifluoromethylated
difluoroacetamides.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(12), С. 1360 - 1366
Опубликована: Фев. 23, 2024
Comprehensive
Summary
The
conversion
of
CF
3
‐alkenes
to
gem
‐difluoroalkenes
using
reductive
cross‐coupling
strategy
has
received
much
attention
in
recent
years,
however,
the
use
green
and
readily
available
reducing
salt
mediate
these
reactions
remains
be
explored.
In
this
work,
a
concise
construction
gem‐
difluoroalkenes,
which
requires
neither
catalyst
nor
metal
agent,
was
established.
Rongalite,
safe
inexpensive
industrial
product,
employed
as
both
radical
initiator
reductant.
This
procedure
compatible
with
linear
cyclic
diaryliodonium
salts,
enabling
wide
variety
substrates
(>70
examples).
utility
approach
demonstrated
through
gram‐scale
synthesis
efficient
late‐stage
functionalizations
anti‐inflammatory
drugs.
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
13(3)
Опубликована: Янв. 8, 2024
Abstract
An
efficient
and
practical
method
for
the
synthesis
of
(β‐trifluoromethyl‐β‐aryl)ethyl
2‐pyridyl
thioethers
via
hydrothiolation
α‐(trifluoromethyl)styrenes
with
pyridine‐2(1
H
)‐thione
was
reported.
The
reaction
proceeded
smoothly
regioselectively
in
an
anti‐Markovnikov
manner
assistance
DBU
afforded
a
variety
trifluoromethyl‐containing
moderate
to
good
yields.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(23), С. 5843 - 5850
Опубликована: Янв. 1, 2023
A
chromium-catalyzed
reductive
allylic
defluorinative
acylation
of
trifluoromethyl-substituted
alkenes
with
acyl
oxime
esters
has
been
developed,
allowing
for
efficient
synthesis
various
ketones
bearing
a
gem
-difluoroalkene
unit.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8342 - 8356
Опубликована: Май 31, 2024
A
mild
and
transition-metal-free
defluorinative
alkylation
of
benzyl
amines
with
trifluoromethyl
alkenes
is
reported.
The
features
this
protocol
are
easy-to-obtain
starting
materials,
a
wide
range
substrates,
functional
group
tolerance
as
well
high
atom
economy,
thus
offering
strategy
to
access
variety
Green Chemistry,
Год журнала:
2024,
Номер
26(15), С. 8694 - 8700
Опубликована: Янв. 1, 2024
Visible-light-induced
hydroxycarboxylation
of
α-trifluoromethylstyrenes
under
an
air
atmosphere
was
developed
to
construct
densely
functionalized
α-CF
3
tertiary
alcohols.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(14), С. 2416 - 2421
Опубликована: Июнь 27, 2023
Abstract
A
dehydrogenative
fluorination
method
is
developed
to
access
multi‐substituted
trifluoromethylalkenes
starting
from
a
variety
of
gem
‐difluoroalkenes.
The
reaction
proceeds
with
electrophilic
source
NFSI
only
and
accommodates
wide
range
functional
groups,
thus
complementing
the
previously
reported
protocols.
Additionally,
visible‐light‐promoted
stereoinversion
revealed
enable
E
‐isomer
enriched
products.
