Synlett,
Год журнала:
2024,
Номер
36(02), С. 97 - 102
Опубликована: Май 28, 2024
Abstract
While
enantioselective
hydrofluorination
methods
for
activated
alkenes
represent
a
notable
advance,
the
resultant
enantiomeric
excesses
remain
largely
moderate,
indicating
necessity
enhancements
in
precision,
efficiency,
and
scope.
We
have
recently
developed
an
innovative
nickel
hydride
catalytic
system
that
enables
regio-
C–F
bond
formation
with
unactivated
alkenes.
By
utilizing
specially
designed
Bn-BOx
ligands
improved
selectivity,
our
approach
demonstrates
exceptional
efficiency
selectivity
β,γ-alkenyl
amide
substrates.
This
breakthrough
enhances
synthesis
of
organofluorine
compounds,
marking
significant
advancement
organic
synthesis.
1
Introduction
2
Reaction
Design
Hydrofluorination
3
Regio-
Enantioselective
4
Asymmetric
Amplification
5
Conclusions
ACS Catalysis,
Год журнала:
2024,
Номер
14(22), С. 16570 - 16576
Опубликована: Окт. 25, 2024
The
reactivity
of
allenes
has
historically
been
limited
with
no
previous
examples
their
hydroalkylation
using
diazo
compounds
in
any
transition-metal
catalytic
framework.
In
this
study,
we
present
a
Ni-catalyzed
regio-
and
stereoselective
reaction
utilizing
as
alkylating
agents.
success
method
can
be
attributed
to
the
use
pyridine-based
P,N
ligand,
which
combines
advantages
both
phosphine
nitrogen
ligands.
Additionally,
carbonyl
group
compound
facilitates
formation
stable
intermediates.
Our
detailed
mechanistic
studies
reveal
that
proceeds
through
an
initial
interaction
compound,
followed
by
engagement
allene.
An
effective
path
for
acid-catalyzed
regioselective
remote
heteroarylation
and
reductive
alkylation
of
alkenes
is
reported,
which
exhibits
excellent
functional
group
compatibility,
regioselectivity,
practicality
potential
applications.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(20)
Опубликована: Март 20, 2024
Abstract
Cyclopropylmethyl
sulfides
react
with
N
‐fluorosulfonimide
(NFSI)
or
molecular
iodine,
enabling
C−S
cleavage
to
generate
cyclopropylcarbinyl
cations,
which
evolve
through
cyclopropane
ring‐opening
reactions
into
homoallyl
cations
suitable
nucleophiles
present
in
the
reaction
media.
This
desulfurative
of
cyclopropylmethyl
thioethers
under
non‐acidic
conditions
facilitates
homoallylation
‐based
such
as
alkyl
aryl
amines
well
sulfonimides
a
one‐pot
protocol
one
two
steps
depending
on
nucleophile.
The
is
initiated
by
halogen‐sulfur
bond
that
causes
cleavage.
Moreover,
iodine
proceeds
iodide
intermediates.
Synlett,
Год журнала:
2024,
Номер
36(02), С. 97 - 102
Опубликована: Май 28, 2024
Abstract
While
enantioselective
hydrofluorination
methods
for
activated
alkenes
represent
a
notable
advance,
the
resultant
enantiomeric
excesses
remain
largely
moderate,
indicating
necessity
enhancements
in
precision,
efficiency,
and
scope.
We
have
recently
developed
an
innovative
nickel
hydride
catalytic
system
that
enables
regio-
C–F
bond
formation
with
unactivated
alkenes.
By
utilizing
specially
designed
Bn-BOx
ligands
improved
selectivity,
our
approach
demonstrates
exceptional
efficiency
selectivity
β,γ-alkenyl
amide
substrates.
This
breakthrough
enhances
synthesis
of
organofluorine
compounds,
marking
significant
advancement
organic
synthesis.
1
Introduction
2
Reaction
Design
Hydrofluorination
3
Regio-
Enantioselective
4
Asymmetric
Amplification
5
Conclusions
