Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
13(1)
Опубликована: Ноя. 21, 2023
Abstract
A
wide
range
of
polyaryl
compounds
(π‐extended
biaryls)
including
terphenyls,
tetraphenyls,
pentaphenyls,
and
hexaphenyls
were
assembled
in
a
single
operation
Pd(II)‐catalyzed
C−H
coupling
biaryl
carboxamides
iodobiaryls.
Traditionally,
cross‐coupling
protocols
involving
organometallic
reagents
employed
to
assemble
the
core
structure
π‐extended
biaryls
(polyphenylenes
or
polyaryls).
The
pre‐assembling
is
limitation
investigations
pertaining
aryl‐aryl
reactions
affording
polyaryls
(polyphenylenes).
We
report
application
bidentate
directing
group
(DG)‐aided
arylation
method
for
constructing
motifs
using
biaryl‐based
iodobiaryls
as
partners
operation.
current
investigation
on
DG‐aided
with
expected
serve
useful
route
enrich
library
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
This
work
describes
the
development
of
a
heterobimetallic
Pd(
ii
)/Cu(
)-catalyzed
C–H
olefination
2-benzamidopyridine
1-oxide
with
acrylates
followed
by
intramolecular
aza-Michael
addition
to
construct
desired
isoindolinone
core.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(6), С. 1279 - 1298
Опубликована: Янв. 1, 2024
Chemical
transformations
involving
pyrenylglycine
are
seldom
known.
This
paper
reports
the
synthesis
of
C(2)-arylated
(an
unnatural
amino
acid)
motifs
via
a
Pd(
ii
)-catalyzed
C–H
functionalization
and
arylation
in
non-K-region
pyrene.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(31)
Опубликована: Июнь 20, 2023
Abstract
This
paper
describes
Pd(II)‐catalyzed
picolinamide‐directed
intermolecular
arylation
and
benzylation
of
remote
δ
−C(sp
2
)−H
bond
(C(2)
position)
the
aryl
ring
in
tyrosine
derivatives
expansion
library
unnatural
tyrosine.
Various
racemic
enantiopure
bis
C(2)
(
ortho
C−H)
arylated
benzylated
were
assembled
good
yields.
Removal
picolinoyl
moiety
after
C(2)−H
assembling
tyrosine‐based
peptides
using
tyrosines
shown.
Tyrosine
biaryl
amino
acids
are
vital
scaffolds
medicinal
chemistry.
Correspondingly,
this
work
is
a
contribution
towards
with
biaryl‐
or
terphenyl
diarylmethane‐based
scaffolds.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(29)
Опубликована: Июнь 13, 2023
Abstract
This
paper
describes
the
Pd(II)‐catalyzed,
picolinamide‐directing‐group‐aided
C(sp
2
)−H
(
ortho
)
functionalization
of
racemic
and
enantiopure
β
‐phenylalanines
3‐amino‐3‐phenylpropanols
(1,3‐amino
alcohols).
The
functionalizations
including
arylation,
bromination,
iodination,
alkoxylation
were
attempted.
arylation
reactions
gave
biaryl
or
terphenyl‐type
‐phenylalanine
scaffolds,
halogenation
methoxylation
C−H
halogenated
methoxylated
‐phenylalanines.
Additionally,
an
‐methyl
substituted
containing
both
remote
3
bonds
was
investigated.
‐Phenylalanine
is
arylated
‐amino
acid
motif
present
in
various
natural
products,
bioactive
molecules,
‐peptides
it
a
precursor
to
medicinally
active
compounds.
Accordingly,
this
work
contributes
expansion
library
unnatural
acid)
derivatives
through
site‐selective
functionalization.
Synthesis,
Год журнала:
2023,
Номер
55(21), С. 3535 - 3567
Опубликована: Март 16, 2023
Abstract
We
report
the
Pd(II)-catalyzed
β-C–H
arylation,
alkylation,
benzylation,
and
methoxylation
of
carbazole-3-carboxamide
carbazole-2-carboxamide
substrates,
assisted
by
bidentate
directing
groups
8-aminoquinoline
or
2-(methylthio)aniline,
construction
C2,C3,C4-functionalized
carbazole
motifs.
The
arylation
reaction
was
attempted
using
different
such
as
8-aminoquinoline,
4-amino-2,1,3-benzothiadiazole,
4-methoxyquinolin-8-amine,
butan-1-amine.
Through
optimization
reactions,
2-(methylthio)aniline
were
found
to
be
suitable
and,
especially,
an
efficient
group
in
carbazole-3-carboxamide,
substrates.
An
ample
number
arylated,
alkylated,
benzylated,
methoxylated
carbazole-3-carboxamides
synthesized.
structures
representative
β-C(2)–H
arylated
motifs
unequivocally
confirmed
single-crystal
X-ray
structure
analysis.
Given
wide
range
applications
carbazoles
chemistry,
materials
sciences,
medicinal
chemistry
there
have
been
constant
efforts
for
developing
new
methods
synthesizing
functionalized
carbazoles.
This
work
contributes
expansion
library
through
a
directing-group-aided
site-selective
activation
functionalization
carbazole-3-carboxamides.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(45), С. 8916 - 8944
Опубликована: Янв. 1, 2024
We
described
the
application
of
C–H
functionalization
for
constructing
carbazole-based
biaryls
and
their
anticancer
activities
in
cancer
cell
lines,
e.g.
,
HeLa,
HCT116,
MDA-MB-231
MDA-MB-468
human
embryonic
kidney
line
HEK293T.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(34)
Опубликована: Июль 8, 2023
Abstract
A
cobalt‐catalyzed,
N,O‐bidentate
directing
group‐assisted
C−H
bond
functionalization
of
benzamides
with
maleimides
was
developed
for
the
facile
access
to
isoindolone
spirosuccinimides
in
good
excellent
yields.
This
activation
and
spirocyclization
employing
pyridine
N‐oxide
as
group
provided
very
substrate
scope
tolerated
various
functional
groups.
Furthermore,
mechanistic
investigation
revealed
that
is
rate‐determining
step
this
reaction.
Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(12)
Опубликована: Ноя. 17, 2022
Abstract
Expanding
the
availability,
scope,
and
limitations
of
directing
groups
(DGs)
for
executing
site‐selective
C−H
activation
functionalization
substrate
scope
development
are
valuable
efforts.
This
paper
reports
extension
utility
4‐amino‐2,1,3‐benzothiadiazole
(ABTD)
group
in
Pd(II)‐catalyzed
arylation
remote
sp
2
/sp
3
γ‐C−H
bonds
aromatic
carboxamides
β
‐C−H
amino
acid
carboxamides.
The
performance
ABTD
DG
was
compared
with
other
known
DGs.
For
example,
we
have
observed
that
mono
methyl
alanine
carboxamide
possessing
iodopyridine
yielded
pyridylalanine
derivative.
Conversely,
same
reaction
using
8‐AQ
did
not
yield
expected
Furthermore,
2,1,3‐benzothiadiazole
moiety‐containing
compounds
an
important
class
molecules
materials
chemistry
medicinally
relevant
molecules.
While
this
work
reveals
as
including
derivatives.
On
hand,
indirectly
process
ABTD‐aided
reactions
has
enabled
to
accomplish
synthesis
a
library
moiety
containing
new
New Journal of Chemistry,
Год журнала:
2024,
Номер
48(21), С. 9424 - 9428
Опубликована: Янв. 1, 2024
We
present
a
novel
deoxygenation
method
of
heterocyclic
N
-oxides
catalyzed
by
iodide
(MgI
2
)
and
regenerated
formic
acid.
Mechanistic
insights
are
provided
through
DFT
investigations.
