The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(9), С. 5893 - 5899
Опубликована: Апрель 18, 2023
Allenyl
carbonate
was
used
as
a
1,3-butadiene
surrogate
to
develop
photocatalytically
sustainable
protocol
for
cobalt-catalyzed
crotylation
of
aldehydes.
The
developed
method
tolerated
wide
range
aromatic
and
aliphatic
aldehydes
with
retention
functional
groups
under
mild
conditions
produced
good-to-excellent
yields
crotylated
secondary
alcohols.
Based
on
preliminary
mechanistic
studies
literature
precedents,
plausible
mechanism
is
proposed.
ACS Catalysis,
Год журнала:
2023,
Номер
13(18), С. 12238 - 12268
Опубликована: Сен. 1, 2023
Organofluorine
compounds
have
attracted
extensive
attention
in
various
industrial
fields
due
to
their
unique
chemical
and
physical
properties.
Despite
increasing
demand
a
wide
range
of
scientific
fields,
the
synthesis
organofluorine
still
faces
several
problems,
such
as
difficulties
handling
fluorinating
reagents
control
chemoselectivity.
Compared
with
formation
C–F
bonds,
activation
functionalization
carbon–fluorine
bonds
is
very
important
but
challenging
topic
synthetic
chemistry.
Due
properties
nickel,
Ni-catalyzed
defluorinative
cross-couplings
been
greatly
developed
past
few
decades
powerful
strategies
for
construction
fluorinated
organic
compounds.
This
Review
summarizes
advances
cross-coupling
aryl
fluorides,
gem-difluorovinyl
trifluoromethyl
Organic Letters,
Год журнала:
2022,
Номер
24(14), С. 2705 - 2710
Опубликована: Апрель 5, 2022
We
report
the
transition-metal-free
defluorinative
C-C
bond-forming
reaction
of
trifluoromethyl
alkenes
with
gem-(diborylalkyl)lithiums.
This
synthetic
strategy
provides
access
to
a
variety
4,4-difluoro
homoallylic
diboronate
esters,
which
serve
as
versatile
intermediates
in
efficient
preparation
valuable
gem-difluoroalkene
derivatives.
Further
modifications
are
conducted
demonstrate
utility
obtained
esters.
Organic Process Research & Development,
Год журнала:
2023,
Номер
27(3), С. 423 - 447
Опубликована: Фев. 17, 2023
Nonprecious-metal-catalyzed
alternatives
to
powerful
precious
metal
transformations
are
of
increasing
interest
in
academia
and
the
pharmaceutical
industry
due
lower
cost,
better
sustainability,
toxicity.
With
continual
growth
broad
field
nonprecious
catalysis
(NPMC),
we
have
chosen
highlight
selected
articles
published
from
March
June
2022
which
intended
examples
NPMC
that
feel
may
be
especially
relevant
development.
We
aim
inspire
academic
industrial
innovation
through
discussion
herein.
Organic Letters,
Год журнала:
2023,
Номер
25(51), С. 9124 - 9129
Опубликована: Ноя. 17, 2023
Herein,
we
describe
a
novel
and
efficient
photoredox
catalytic
Cα
radical
addition/defluoroalkylation
coupling
reaction
between
α-trifluoromethyl
alkenes
N-trifluoroethyl
hydroxylamine.
A
series
of
gem-difluoroallylated
α-trifluoromethylamines
were
synthesized
by
the
addition
enabled
1,2-H
shift
in
situ-generated
radical.
Notably,
this
protocol
is
distinguished
its
mild
conditions,
easy
operation,
excellent
functional
group
tolerability.
Organic Letters,
Год журнала:
2024,
Номер
26(13), С. 2656 - 2661
Опубликована: Март 25, 2024
We
disclose
a
photocatalytic
strategy
that
simultaneously
addresses
the
construction
of
trifluoromethylated
quaternary
carbon
centers
and
preparation
β-CF3-enones
through
radical
difunctionalization
α-CF3
alkenes
with
acyl
chlorides.
This
method
is
characterized
by
its
broad
functional
group
compatibility,
high
efficiency,
atom
economy.
The
versatility
this
transformation
poised
to
broaden
applications
alkenes,
providing
new
pathways
for
rapid
assembly
structurally
diverse
fluorinated
compounds.
Organic Letters,
Год журнала:
2022,
Номер
24(17), С. 3211 - 3216
Опубликована: Апрель 28, 2022
In
this
protocol,
we
demonstrate
our
discovery
that
iron
is
able
to
efficiently
catalyze
the
reductive
allylic
defluorinative
ketyl
olefin
coupling
reaction
between
α-trifluoromethyl
alkenes
and
unactivated
ketones.
This
operationally
simple
cross-electrophile
circumvents
use
of
pre-generated
organometallics
allows
for
synthesis
diverse
functional-group-rich
tertiary
gem-difluorohomoallylic
alcohols
through
a
polarity-reversed
strategy.
Preliminary
mechanistic
studies
support
mechanism
proceeds
formation/olefin
insertion/β-fluoro
elimination
sequence.
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.
Chemical Communications,
Год журнала:
2023,
Номер
59(35), С. 5213 - 5216
Опубликована: Янв. 1, 2023
gem
-Difluoroallylic
bicyclo[1.1.1]pentanes
were
synthesized
via
visible
light-induced
defluorinative
-difluoroallylation
of
[1.1.1]propellane
under
mild
conditions
with
good
functional
group
tolerance.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(8), С. 1981 - 1987
Опубликована: Янв. 1, 2023
A
photoinduced
radical
[1,2]-Brook
rearrangement/defluorinated
alkylation
reaction
of
α-trifluoromethyl
alkenes
with
α-silyl
alcohols
was
developed
for
facile
access
to
gem
-difluoro
homoallylic
alcohol
derivatives.
Organic Letters,
Год журнала:
2023,
Номер
25(8), С. 1336 - 1341
Опубликована: Фев. 23, 2023
A
concise
Fe-catalyzed
alkylazidation
of
α-trifluoromethylalkenes
via
a
C–C
bond
cleavage/radical
addition/azidation
cascade
is
described.
This
protocol
features
broad
substrate
scope,
excellent
functional
group
compatibility,
and
the
ability
to
be
performed
on
gram
scale,
thus
offering
practical
step-economic
approach
synthetically
useful
tertiary
α-trifluoromethyl
azides.
