Chemical Science,
Год журнала:
2020,
Номер
12(5), С. 1834 - 1842
Опубликована: Дек. 8, 2020
Intermolecular
asymmetric
haloamination
reactions
are
challenging
due
to
the
inherently
high
halenium
affinity
(HalA)
of
nitrogen
atom,
which
often
leads
N-halogenated
products
as
a
kinetic
trap.
To
circumvent
this
issue,
acetonitrile,
possessing
low
HalA,
was
used
nucleophile
in
catalytic
Ritter-type
chloroamidation
allyl-amides.
This
method
is
compatible
with
Z
and
E
alkenes
both
alkyl
aromatic
substitution.
Mild
acidic
workup
reveals
1,2-chloroamide
enantiomeric
excess
greater
than
95%
for
many
examples.
We
also
report
successful
use
sulfonamide
chlorenium
reagent
dichloramine-T
chlorenium-initiated
reaction.
Facile
modifications
lead
chiral
imidazoline,
guanidine,
orthogonally
protected
1,2,3
tri-amines.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 23, 2024
Abstract
The
high
utility
of
halogenated
organic
compounds
has
prompted
the
development
numerous
transformations
that
install
carbon‐halogen
motif.
Halogen
functionalities,
deemed
as
“functional
and
functionalizable”
molecules
due
to
their
capacity
modulate
diverse
internal
properties,
constitute
a
pivotal
strategy
in
drug
discovery
development.
Traditional
routes
these
building
blocks
have
commonly
involved
multiple
steps,
harsh
reaction
conditions,
use
stoichiometric
and/or
toxic
reagents.
With
emergence
solid
halogen
carriers
such
N
‐halosuccinimides,
halohydantoins
popular
sources
halonium
ions,
past
decade
witnessed
enormous
growth
new
catalytic
strategies
for
halofunctionalization.
This
review
aims
provide
nuanced
perspective
on
nucleophilic
activators
roles
activation.
It
will
highlight
critical
discoveries
effecting
racemic
asymmetric
variants
reactions,
driven
by
catalysts,
activation
modes,
improved
understanding
chemical
reactivity
kinetics.
European Journal of Organic Chemistry,
Год журнала:
2021,
Номер
2021(19), С. 2788 - 2791
Опубликована: Апрель 21, 2021
Abstract
The
weakly
coordinating
dianion
[B
12
Cl
]
2−
originates
from
a
family
of
carboranes
typically
reserved
for
application
in
coordination
chemistry.
Herein,
we
show
that
its
readily
accessible
Ag(I)
salt,
[Ag]
2
],
can
be
used
as
catalyst
the
PhICl
mediated
chlorination
arenes,
alkenes,
and
alkynes.
promising
activity
displayed
by
over
variety
commercially
available
sources
merits
incorporation
to
toolkit
commonly
screened
silver
catalysts
synthesis.
Chemistry - A European Journal,
Год журнала:
2021,
Номер
27(69), С. 17341 - 17345
Опубликована: Окт. 14, 2021
The
first
example
for
the
electrochemical
cis-dichlorination
of
alkenes
is
presented.
reaction
can
be
performed
with
little
experimental
effort
by
using
phenylselenyl
chloride
as
catalyst
and
tetrabutylammoniumchloride
supporting
electrolyte,
which
also
acts
nucleophilic
reagent
S
Synthetic Communications,
Год журнала:
2020,
Номер
50(15), С. 2319 - 2330
Опубликована: Июнь 5, 2020
Rui
Dinga*,
Shuai
Huanga*,
Qiyi
Wanga,
Yongguo
Liua,
Baoguo
Suna
&
Hongyu
Tiana*a
Beijing
Advanced
Innovation
Center
for
Food
Nutrition
and
Human
Health,
Key
Laboratory
of
Flavor
Chemistry,
Technology
Business
University,
Beijing,
China
Chemical Science,
Год журнала:
2020,
Номер
12(5), С. 1834 - 1842
Опубликована: Дек. 8, 2020
Intermolecular
asymmetric
haloamination
reactions
are
challenging
due
to
the
inherently
high
halenium
affinity
(HalA)
of
nitrogen
atom,
which
often
leads
N-halogenated
products
as
a
kinetic
trap.
To
circumvent
this
issue,
acetonitrile,
possessing
low
HalA,
was
used
nucleophile
in
catalytic
Ritter-type
chloroamidation
allyl-amides.
This
method
is
compatible
with
Z
and
E
alkenes
both
alkyl
aromatic
substitution.
Mild
acidic
workup
reveals
1,2-chloroamide
enantiomeric
excess
greater
than
95%
for
many
examples.
We
also
report
successful
use
sulfonamide
chlorenium
reagent
dichloramine-T
chlorenium-initiated
reaction.
Facile
modifications
lead
chiral
imidazoline,
guanidine,
orthogonally
protected
1,2,3
tri-amines.
