Molecules,
Год журнала:
2024,
Номер
29(24), С. 6016 - 6016
Опубликована: Дек. 20, 2024
Nitriles
are
valuable
compounds
because
they
have
widespread
applications
in
organic
chemistry.
This
report
details
the
nickel-catalyzed
reductive
cyanation
of
aryl
halides
and
epoxides
with
cyanogen
bromide
for
synthesis
nitriles.
robust
protocol
underscores
practicality
using
a
commercially
available
cost-effective
reagent.
A
variety
featuring
diverse
functional
groups,
such
as
-TMS,
-Bpin,
-OH,
-NH2,
-CN,
-CHO,
were
successfully
converted
into
nitriles
moderate-to-good
yields.
Moreover,
syntheses
at
gram-scale
application
late-stage
natural
products
drugs
reinforces
its
potentiality.
ACS Organic & Inorganic Au,
Год журнала:
2024,
Номер
4(3), С. 287 - 300
Опубликована: Март 4, 2024
In
the
past
5
years,
hexafluoroisopropanol
(HFIP)
has
been
used
as
a
unique
solvent
or
additive
to
enable
challenging
transformations
through
substrate
activation
and
stabilization
of
reactive
intermediates.
this
Review,
we
aim
at
describing
difunctionalization
processes
which
were
unlocked
when
HFIP
was
involved.
Specifically,
focus
on
cyclizations
additions
alkenes,
alkynes,
epoxides,
carbonyls
that
introduce
wide
range
functional
groups
interest.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(22)
Опубликована: Март 19, 2024
Abstract
We
reveal
here
a
catalyst‐free,
ring‐opening‐cyclization
of
donor‐acceptor
cyclopropanes
with
primary
amines
to
synthesize
functionalized
dihydropyrroles.
This
protocol
avoids
inert
conditions
and
solvents
promoted
by
hexafluoroisopropanol
(HFIP).
The
reaction
is
quite
general
aryl,
alkyl,
alicyclic
amines.
A
good
number
bearing
keto
groups
reacted
excellently
produce
the
desired
products.
Further,
we
complemented
this
method
Meldrum's
acid‐derived
for
synthesizing
γ‐lactams.
have
demonstrated
post‐synthetic
applications
products
gram‐scale
synthesis
highlight
adaptability
synthetic
protocol.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
62(9)
Опубликована: Дек. 21, 2022
β-Arylethylamines
are
prevalent
structural
motifs
in
molecules
exhibiting
biological
activity.
Here
we
report
a
sequential
one-pot
protocol
for
the
1,2-aminoarylation
of
alkenes
with
hydroxylammonium
triflate
salts
and
(hetero)arenes.
Unlike
existing
methods,
this
reaction
provides
direct
entry
to
unprotected
β-arylethylamines
remarkable
functional
group
tolerance,
allowing
key
drug-oriented
groups
be
installed
two-step
process.
The
use
hexafluoroisopropanol
as
solvent
combination
an
iron(II)
catalyst
proved
essential
reaching
high-value
nitrogen-containing
molecules.
Chemical Science,
Год журнала:
2023,
Номер
14(11), С. 2983 - 2989
Опубликована: Янв. 1, 2023
The
use
of
epoxides
as
aldehyde
surrogates
allows
isochromans
to
be
constructed
with
greater
scope
than
previously
reported
oxa-Pictet–Spengler
reactions.
initial
Meinwald
rearrangement
and
subsequent
steps
are
promoted
by
HFIP
triflic
acid.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2726 - 2740
Опубликована: Фев. 2, 2024
A
facile
and
efficient
approach
for
the
synthesis
of
multisubstituted
tetrahydropyridazines
starting
from
cyclopropyl
ketones
hydrazines
has
been
developed.
The
transformation
is
chalcone-based
takes
place
via
a
Cloke–Wilson-type
rearrangement-involved
tandem
reaction
catalyzed
by
TfOH
in
HFIP.
Organic Letters,
Год журнала:
2024,
Номер
26(15), С. 2934 - 2938
Опубликована: Март 29, 2024
Natural
sesquiterpenoid
lactones
are
prominent
scaffolds
in
drug
discovery.
Despite
the
progress
made
their
synthesis,
extensive
oxidative
decoration
makes
chemo-
and
stereoselective
syntheses
highly
challenging.
Herein,
we
report
our
effort
to
mimic
part
of
oxidase
phase
used
costunolide
pathway
achieve
protecting-group-free
total
synthesis
santamarine,
dehydrocostus
lactone,
estafiatin,
nine
more
related
natural
by
using
dioxygen
as
sole
oxidant.
Organic Letters,
Год журнала:
2023,
Номер
25(27), С. 4956 - 4961
Опубликована: Июнь 29, 2023
A
novel
and
unprecedented
p-toluenesulfonic
acid-catalyzed
dehydrative
Nazarov-type
cyclization/C2-N1
bond
cleavage
cascade
reaction
of
perfluoroalkylated
3-indolyl(2-benzothienyl)methanols
has
been
developed.
This
provides
an
efficient
practical
protocol
for
the
construction
highly
functionalized
benzothiophene-fused
cyclopentenones
with
exclusive
stereoselectivity.
In
addition,
this
transformation
also
delineates
a
rare
example
involvement
selective
C2-N1
indoles.
Abstract
Here,
the
evolution
of
titanocene‐catalyzed
hydrosilylation
epoxides
that
yields
corresponding
anti‐Markovnikov
alcohols
is
summarized.
The
study
focuses
on
aspects
sustainability,
efficient
catalyst
activation,
and
stereoselectivity.
latest
variant
reaction
employs
polymethylhydrosiloxane
(PMHS),
a
waste
product
Müller–Rochow
process
as
terminal
reductant,
features
an
activation
with
benzylMgBr
use
bench
stable
Cp
2
TiCl
precatalyst.
combination
olefin
epoxidation
epoxide
provides
uniquely
approach
to
formal
addition
H
O
olefins.
Abstract
Here,
we
describe
that
polymethylhydrosiloxane
(PMHS)
is
a
sustainable
terminal
reductant
in
the
titanocene
catalyzed
hydrosilylation
of
epoxides.
The
products
formally
constitute
anti
‐Markovnikov
H
2
O‐addition
to
alkenes.
PMHS
not
only
more
and
cheaper
than
other
silanes
such
as
PhSiH
3
Ph(Me)SiH
.
It
also
results
higher
diastereoselectivity
epoxide
reduction.
