Scientia Sinica Chimica,
Год журнала:
2022,
Номер
53(3), С. 410 - 422
Опубликована: Ноя. 26, 2022
Aromatic
amines
are
widely
used
in
the
fields
of
natural
products,
pharmaceutical
chemistry
and
materials
science,
thus
new
methods
metal-catalyzed
C–N
bond
coupling
for
constructing
aromatic
always
have
been
focus
attention
chemists
scientific
community.
Copper,
as
a
catalyst
amination
arenes,
has
attracted
extensive
due
to
its
unique
catalytic
performance
variety
oxidation
states.
In
this
review,
recent
progress
construction
compounds
C(sp2)–N
catalyzed
by
copper
is
reviewed,
reaction
mechanisms
representative
reactions
briefly
described.
ACS Catalysis,
Год журнала:
2021,
Номер
11(13), С. 7772 - 7779
Опубликована: Июнь 13, 2021
Despite
the
significant
success
of
metal-H-catalyzed
hydroamination
methodologies,
considerable
limitations
still
exist
in
selective
alkynes,
especially
for
terminal
alkynes.
Herein,
we
develop
a
highly
efficient
NiH
catalytic
system
that
activates
readily
available
alkynes
cascade
hydroamination/cyclization
reaction
with
anthranils.
This
mild,
operationally
simple
protocol
is
amenable
to
wide
array
including
and
internal,
aryl
alkyl,
electron-deficient
electron-rich
ones,
delivering
structurally
diverse
quinolines
useful
excellent
yields
(>80
examples,
up
93%
yield).
The
utility
this
procedure
exhibited
late-stage
functionalization
several
natural
products
concise
synthesis
an
antitumor
molecule
graveolinine
triplex
DNA
intercalator.
Preliminary
mechanistic
experiments
suggest
alkenylnickel-mediated
alkyne
intramolecular
cyclization/aromatization
putative
enamine
intermediates.
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
363(2), С. 411 - 424
Опубликована: Ноя. 14, 2020
Abstract
Organic
azides
are
highly
reactive,
which
have
long
established
as
versatile
building
blocks
in
the
assembly
of
structurally
diverse
N‐containing
heterocycles.
The
conversion
organic
into
high‐value
compounds
is
great
importance
and
a
subject
enormous
current
interest.
Transition
metal‐catalyzed
C(
sp
2
)−H
amination/annulation
provides
powerful
tool
for
transformation
wide
range
biologically
important
heterocyclic
frameworks.
In
this
review,
we
aim
to
summarize
recent
progress
on
azides‐mediated
N‐heterocycle
synthesis
enabled
by
transition
metal
catalysts.
Representative
strategies
discussed
detail,
including
catalytic
systems,
reaction
scopes,
limitations
mechanisms.
magnified
image
Asian Journal of Organic Chemistry,
Год журнала:
2021,
Номер
10(12), С. 3127 - 3165
Опубликована: Окт. 11, 2021
Abstract
Isoxazoles
are
an
important
class
of
heterocycles
with
nitrogen
and
oxygen
in
a
1,2‐relationship.
They
find
wide
applications
synthetic
organic
chemistry
part
several
drug
molecules.
Since
the
last
two
decades,
great
progress
has
been
achieved
synthesis
functionalization
isoxazoles,
which
transition
metal
catalysis
played
pivotal
role
towards
achieving
this
goal.
In
particular,
(TM)‐mediated
site‐selective
functionalizations
isoxazoles
retain
pharmacologically
synthetically
valuable
isoxazole
skeleton,
highly
appealing.
This
comprehensive
review
is
solely
dedicated
to
TM‐mediated
wherein
we
have
included
as
directing
groups
(DG)
for
TM‐catalyzed
C−H
reactions,
direct
functionalization,
along
cross‐coupling
reactions
annulation
finally
ring‐opening
under
TM‐catalysis
also
discussed.
Also,
incorporated
discussions
on
reaction
designs,
their
advantages
limitations,
mechanistic
details
challenges
that
need
be
addressed
inspire
medicinal
chemists
explore
new
arenas
make
use
key
scaffold.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(21), С. 14640 - 14651
Опубликована: Окт. 14, 2021
An
unprecedented
Pd-catalyzed
asymmetric
intramolecular
cascade
cyclization
of
aryl
halides
with
readily
available
arylboronic
acids
proceeds
through
a
Heck-type
dearomative
terminated
arylation
in
the
presence
Pd2(dba)3
(10
mol
%),
Cu2O
(5
and
Cs2CO3
(2.0
equiv)
1,2-dichloroethane
(1.0
mL)
at
100
°C
for
15
h
air
using
BINOL-based
phosphoramidite
as
chiral
ligand.
This
Heck
protocol,
which
tolerates
broad
variety
functional
groups,
is
amenable
to
generation
optically
active
indoline
derivatives
bearing
all-carbon
quaternary
stereogenic
centers
one
step
moderate
excellent
yields,
diastereoselectivities
(>20:1)
enantioselectivities
(up
>99%
ee).
It
worth
mentioning
that
no
decrease
enantiopurity
was
observed
during
synthetic
transformations
products.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(17), С. 12107 - 12118
Опубликована: Авг. 24, 2021
A
nickel-catalyzed
polarity-reversed
hydroamination
of
olefins
has
been
achieved
with
anthranils
as
the
electrophilic
aminating
agents
and
hydrosilane
reductant.
This
protocol
provides
a
facile
access
to
N-alkyl-2-aminobenzophenones
that
are
versatile
intermediates
in
organic
synthesis.
wide
range
compatible
this
transformation,
delivering
desired
amines
useful
excellent
yields
(38
examples,
up
92%
yield).
The
utility
is
exhibited
late-stage
functionalization
drug
molecules
valuable
derivatives
obtained
amination
products.
Chemical Science,
Год журнала:
2022,
Номер
13(7), С. 2105 - 2114
Опубликована: Янв. 1, 2022
A
practical
route
for
the
synthesis
of
valuable
3-aryl
anthranils
from
readily
available
and
simple
arenes
has
been
achieved
through
an
electrophilic
substitution
rearomatization
sequence
by
employing
Tf
2
O
as
effective
activator.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(21), С. 14861 - 14869
Опубликована: Окт. 11, 2022
The
regioselective
hydroamination
of
unactivated
alkenes
is
a
long-standing
challenge
in
organic
synthesis.
Herein,
we
report
NiH-catalyzed
proximal-selective
with
8-aminoquinoline
(AQ)
as
bidentate
auxiliary
and
anthranils
aminating
reagents.
A
wide
range
primary
aryl
amines
bearing
an
ortho-carbonyl
group
were
installed
both
terminal
internal
alkenes,
delivering
variety
valuable
β-
γ-amino
acid
building
blocks,
respectively,
excellent
regiocontrol.
utility
this
transformation
was
further
demonstrated
by
the
conversion
multifunctionalized
into
useful
N-heterocycles.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(5), С. 3150 - 3160
Опубликована: Фев. 9, 2024
A
practical
synthesis
of
valuable
N-acyl
anthranilic
acids
has
been
achieved
via
a
silver-catalyzed
imino-ketene
generation
from
readily
available
anthranils
and
carboxylic
acids.
wide
range
including
sterically
demanding
aliphatic
acids,
aromatic
acrylic
amino
are
compatible
in
this
reaction.
Moreover,
method
can
be
used
to
modify
drug
molecules
natural
products,
such
as
ibuprofen,
probenecid,
acetylglycine.
