European Journal of Organic Chemistry,
Год журнала:
2021,
Номер
2021(42), С. 5831 - 5834
Опубликована: Окт. 20, 2021
Abstract
A
general
and
efficient
intramolecular
halo‐amination
of
unactivated
alkenes
for
the
synthesis
various
halogenated
N
‐heterocycles
was
developed
via
electrochemical
anodic
oxidation.
This
protocol
proceeds
in
a
simple
undivided
cell
by
employing
LiI
or
LiBr
as
redox
mediums
halogen
sources.
wide
range
‐heterocycles,
including
three‐,
five‐,
six‐membered
were
constructed
moderate
to
good
yields
at
room
temperature.
Notably,
this
oxidative
transformation
avoids
utilization
external
oxidants
strong
bases,
therefore
represents
an
environmentally
benign
approach.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(10), С. 1685 - 1692
Опубликована: Май 5, 2023
Abstract
Installation
of
an
alkyl
chain
at
a
specified
position
in
the
aromatic
ring
via
metal‐free
catalysis
is
very
important.
In
this
regard,
we
have
developed
facile
metal‐free,
extremely
selective,
user‐friendly,
environmentally
benign
and
cost‐effective
Friedel‐Crafts
(FC)
alkylation
protocol
for
2‐oxindoles
anilines
with
donor‐acceptor
cyclopropanes.
Real‐time
NMR
studies
reveal
that
transformation
governed
by
cooperative
Brønsted
acid
(TfOH)
HFIP,
which
facilitates
nucleophilic
attack
on
cyclopropanes
from
anilines.
magnified
image
Organic Letters,
Год журнала:
2023,
Номер
25(49), С. 8777 - 8781
Опубликована: Окт. 11, 2023
Although
oxygen,
nitrogen,
and
carbon
have
been
extensively
studied
as
nucleophilic
elements
in
the
halocyclization
of
alkenes,
sulfur-based
nucleophiles
are
relatively
unexplored.
Herein,
we
investigated
bromocyclization
chemistry
involving
unsaturated
thioesters,
with
a
focus
on
their
use
potential
S-nucleophiles.
We
developed
method
that
uses
alkenoic
thioesters
N-bromoacetamide
(NBA)
to
form
cyclic
bromosulfides.
The
resulting
5-exo
products
labile
can
be
used
various
substitution
reactions.
Chemical Science,
Год журнала:
2023,
Номер
14(43), С. 12083 - 12090
Опубликована: Янв. 1, 2023
Nitrogen
containing
compounds,
such
as
anilines,
are
some
of
the
most
widespread
and
useful
chemical
species,
although
their
high
unselective
reactivity
has
prevented
incorporation
into
many
interesting
transformations,
functionalization
alkenes.
Herein
we
report
a
method
that
allows
trifluoromethylarylation
alkenes
using
for
first
time,
with
no
need
additives,
transition
metals,
photocatalysts
or
an
excess
reagents.
An
in-depth
mechanistic
study
reveals
key
role
hexafluoroisopropanol
(HFIP)
unique
solvent,
establishing
hydrogen
bonding
network
aniline
trifluoromethyl
reagent,
is
responsible
altered
exquisite
selectivity.
This
work
uncovers
new
mode
involves
use
abundant
anilines
non-prefunctionalized
aromatic
source
simultaneous
activation
hypervalent
iodine
reagent.
ACS Catalysis,
Год журнала:
2022,
Номер
12(12), С. 7046 - 7053
Опубликована: Июнь 1, 2022
Asymmetric
catalysis
with
a
chiral
(Salen)Mn(III)
complex
is
applied
successfully
to
highly
enantioselective
intramolecular
haloamination
reactions
of
alkenes
through
aziridinium
ion
ring-opening
sequence.
Computational
and
experimental
studies
suggested
that
the
C5–C6
bond
polarization
has
major
effect
on
regioselectivity
aziridines
ring
intermediate,
steric
hindrance
groups
at
C5
or
C6
plays
minor
role.
Various
amino-alkenes
can
cyclize
under
reaction
conditions
obtain
2-brominated/chlorinated
pyrrolidine
indoline
derivatives
excellent
yield
enantioselectivity.
European Journal of Organic Chemistry,
Год журнала:
2021,
Номер
2021(42), С. 5831 - 5834
Опубликована: Окт. 20, 2021
Abstract
A
general
and
efficient
intramolecular
halo‐amination
of
unactivated
alkenes
for
the
synthesis
various
halogenated
N
‐heterocycles
was
developed
via
electrochemical
anodic
oxidation.
This
protocol
proceeds
in
a
simple
undivided
cell
by
employing
LiI
or
LiBr
as
redox
mediums
halogen
sources.
wide
range
‐heterocycles,
including
three‐,
five‐,
six‐membered
were
constructed
moderate
to
good
yields
at
room
temperature.
Notably,
this
oxidative
transformation
avoids
utilization
external
oxidants
strong
bases,
therefore
represents
an
environmentally
benign
approach.
