Chemical Reviews,
Год журнала:
2021,
Номер
121(7), С. 4253 - 4307
Опубликована: Фев. 26, 2021
Aliphatic
azides
are
a
versatile
class
of
compounds
found
in
variety
biologically
active
pharmaceuticals.
These
also
recognized
as
useful
precursors
for
the
synthesis
range
nitrogen-based
scaffolds
therapeutic
drugs,
compounds,
and
functional
materials.
In
light
growing
importance
aliphatic
both
chemical
biological
sciences,
vast
array
synthetic
strategies
preparation
structurally
diverse
have
been
developed
over
past
decades.
However,
to
date,
this
topic
has
not
subject
dedicated
review.
This
review
aims
provide
concise
overview
modern
access
that
emerged
since
2010.
The
discussed
azidation
reactions
include
(a)
C–C
multiple
bonds,
(b)
C–H
(c)
direct
transformation
vinyl
into
other
azides,
(d)
miscellaneous
azides.
We
critically
discuss
outcomes
generality
uniqueness
different
mechanistic
rationale
each
selected
reactions.
challenges
potential
opportunities
outlined.
Chemical Reviews,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 13, 2024
Hypervalent
iodine(III)
compounds
have
found
wide
application
in
modern
organic
chemistry
as
environmentally
friendly
reagents
and
catalysts.
iodine
are
commonly
used
synthetically
important
halogenations,
oxidations,
aminations,
heterocyclizations,
various
oxidative
functionalizations
of
substrates.
Iodonium
salts
arylating
reagents,
while
iodonium
ylides
imides
excellent
carbene
nitrene
precursors.
Various
derivatives
benziodoxoles,
such
azidobenziodoxoles,
trifluoromethylbenziodoxoles,
alkynylbenziodoxoles,
alkenylbenziodoxoles
group
transfer
the
presence
transition
metal
catalysts,
under
metal-free
conditions,
or
using
photocatalysts
photoirradiation
conditions.
Development
hypervalent
catalytic
systems
discovery
highly
enantioselective
reactions
chiral
represent
a
particularly
recent
achievement
field
chemistry.
Chemical
transformations
promoted
by
many
cases
unique
cannot
be
performed
any
other
common,
non-iodine-based
reagent.
This
review
covers
literature
published
mainly
last
7-8
years,
between
2016
2024.
Green Synthesis and Catalysis,
Год журнала:
2020,
Номер
1(2), С. 86 - 120
Опубликована: Авг. 6, 2020
The
azido
group
is
found
in
large
numbers
of
natural
products,
drugs,
biochemicals
and
materials
to
date,
many
elegant
useful
methods
for
the
synthesis
organic
azides
their
transformations
have
been
documented.
In
this
review,
we
provide
a
summary
state
art
radical
azidation
construction
C(sp3)-N3
bonds.
There
specific
emphasis
on
synthetic
reactions
involving
C(sp3)-H
azidation,
decarboxylative
difunctionalized
olefins.
This
review
will
be
those
working
field
hopefully
could
inspire
further
development
reactions.
Angewandte Chemie International Edition,
Год журнала:
2021,
Номер
60(49), С. 25640 - 25666
Опубликована: Май 4, 2021
Classical
amination
methods
involve
the
reaction
of
a
nitrogen
nucleophile
with
an
electrophilic
carbon
center;
however,
in
recent
years,
umpoled
strategies
have
gained
traction
where
source
acts
as
electrophile.
A
wide
range
aminating
agents
are
now
available,
and
these
underpin
powerful
C-N
bond-forming
processes.
In
this
Review,
we
highlight
strategic
use
total
synthesis.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
59(39), С. 17239 - 17244
Опубликована: Июнь 10, 2020
The
first
Pd-catalyzed
enantioselective
azidation
of
unactivated
alkenes
has
been
established
by
using
readily
accessible
1-azido-1,2-benziodoxol-3(1H)-one
(ABX)
as
an
azidating
reagent,
which
affords
a
wide
variety
structurally
diverse
3-N3
-substituted
piperidines
in
good
yields
with
excellent
enantioselectivity.
reaction
features
functional-group
compatibility
and
mild
conditions.
Notably,
both
electrophilic
reagent
the
sterically
bulky
chiral
pyridinyl-oxazoline
(Pyox)
ligand
are
crucial
to
successful
reaction.
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Июнь 10, 2024
Chiral
1,2,3-triazoles
are
highly
attractive
motifs
in
various
fields.
However,
achieving
catalytic
asymmetric
click
reactions
of
azides
and
alkynes
for
chiral
triazole
synthesis
remains
a
significant
challenge,
mainly
due
to
the
limited
systems
substrate
scope.
Herein,
we
report
an
enantioselective
azidation/click
cascade
reaction
N-propargyl-β-ketoamides
with
readily
available
potent
azido
transfer
reagent
via
copper
catalysis,
which
affords
variety
up
99%
yield
95%
ee
under
mild
conditions.
Notably,
1,5-disubstituted
triazoles
that
have
not
been
accessed
by
previous
also
prepared
good
functional
group
tolerance.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(18)
Опубликована: Март 9, 2023
Organic
nitrates
are
broadly
applied
as
pharmaceuticals
(acting
efficient
nitric
oxide
donor),
energetic
materials,
building
blocks
in
organic
synthesis,
etc.
However,
practical
and
direct
methods
to
access
efficiently
still
rare,
mainly
due
the
lack
of
powerful
nitrooxylating
reagents.
Herein,
we
report
bench-stable
highly
reactive
noncyclic
hypervalent
iodine
reagents,
oxybis(aryl-λ3
-iodanediyl)
dinitrates
(OAIDNs,
2),
which
prepared
just
by
using
aryliodine
diacetate
HNO3
.
The
reagents
used
achieve
a
mild
operationally
simple
protocol
diverse
nitrates.
By
employing
2,
zinc-catalyzed
regioselective
nitrooxylation
cyclopropyl
silyl
ethers
is
realized
corresponding
β-nitrooxy
ketones
with
high
functional-group
tolerance.
Moreover,
series
catalyst-free
nitrooxylations
enolizable
C-H
bonds
carried
out
smoothly
afford
desired
within
minutes
mixing
substrates
2
dichloromethane.
Organic Letters,
Год журнала:
2023,
Номер
25(15), С. 2739 - 2744
Опубликована: Апрель 12, 2023
Both
azido
(N3)
and
trifluoromethyl
(CF3)
groups
are
key
moieties
of
numerous
valuable
molecules
that
extensively
applied
in
drug
discovery,
chemical
biology,
synthetic
chemistry.
However,
the
asymmetric
construction
chiral
quaternary
stereocenters
bearing
both
N3
CF3
is
still
unexplored.
Herein,
we
report
a
kind
bench-stable
easily
adjustable
benziodazolone-based
azidating
reagents.
These
reagents
were
used
to
achieve
an
enantioselective
copper-catalyzed
azidation
N-unprotected
3-trifluoromethylated
oxindoles
provide
diverse
enantioenriched
3-N3-3-CF3
oxindoles.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(20), С. 4238 - 4243
Опубликована: Март 16, 2024
Abstract
The
catalytic
asymmetric
dearomative
arylation
of
2‐naphthols
enabled
by
the
unconventional
reactivity
o
‐quinone
diimides,
i.
e.
1,4‐conjugate
addition
on
quinone
sp
2
hybridized
carbon,
has
been
established.
Under
catalysis
chiral
phosphoric
acid,
various
cyclohexaenones
bearing
an
all‐carbon
quaternary
stereocenter
have
prepared
with
excellent
yields
and
enantioselectivities.
