Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(12)
Published: Nov. 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
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(50), P. 9259 - 9263
Published: Dec. 14, 2022
This
paper
describes
the
nickel-catalyzed
reductive
alkylation
of
aroyl
fluorides
with
alkyl
bromides
in
a
decarbonylative
manner.
In
this
reaction,
various
functional
groups
are
well
tolerated
and
C(sp2)-C(sp3)
bond
can
be
constructed
directly
without
use
organometallic
reagents.
The
present
reaction
is
cross-electrophile
coupling
via
radical
pathway,
affording
corresponding
alkylarenes
moderate
to
good
yields.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(21), P. 4391 - 4414
Published: Jan. 1, 2022
Synthesis
of
racemic
and
enantiopure
carbazole-based
unnatural
amino
acid
motifs
was
accomplished
via
diastereoselective
Pd(
ii
)-catalyzed
β-C(sp
3
)–H
functionalization.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(31)
Published: June 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,
Journal Year:
2024,
Volume and Issue:
27(13)
Published: Feb. 15, 2024
Abstract
Direct
C−H
functionalization
is
an
important
strategy
for
the
rapid
synthesis
of
valuable
organic
molecules.
Radical‐involved
remote
C(sp
3
)‐H
based
on
hydrogen
atom
transfer
(HAT)
becomes
method
enabling
selective
direct
transformation
bonds
at
specific
distal
position(s).
In
recent
years,
copper‐catalyzed
fluoroamide‐directed
bond
through
intramolecular
HAT
has
served
as
a
robust
and
elegant
assembly
variety
functionalized
(sulfon)amides
related
derivatives.
This
review
focuses
advances
in
this
area.
These
transformations
proceed
effectively
with
high
selectivities
good
functional
group
compatibility
under
mild
conditions.
Chemical Society Reviews,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
This
review
provides
an
overview
of
the
research
advaces
in
Ni-,
Cu-,
Fe-
and
Co-catalyzed
directed
C(sp
3
)–H
bond
functionalization
reactions;
including
design
principles,
mechanistic
discussions,
along
with
potential
applications
limitations.
ACS Omega,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 21, 2025
This
study
describes
the
utility
of
Pd(II)-catalyzed
C-H
arylation
benzamides
for
constructing
biaryl
sulfonamides.
Sulfonamides
are
known
their
promising
applications
in
pharmaceuticals
and
agrochemicals.
A
literature
review
revealed
that
sulfonamides
were
generally
constructed
via
traditional
cross-coupling
reactions.
We
report
a
progressive
method
obtaining
bidentate
directing
group
(8-aminoquinoline
or
picolinamide)-assisted
sp2
bonds
aromatic
carboxamides
with
iodobenzenesulfonamides.
After
reactions,
we
attempted
removal
8-aminoquinoline
from
synthesized
scaffolds
possessing
carboxamide
sulfonamide
moieties
using
triflic
acid.
In
some
cases,
observed
occurrence
decarboxylation
Friedel-Crafts
acylation,
affording
interesting
moiety.
The
current
work
contributes
toward
developing
alternative
ways
assembling
various
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(6), P. 1279 - 1298
Published: Jan. 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.
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(9)
Published: July 8, 2022
Abstract
We
have
shown
our
efforts
toward
expanding
the
utility
of
relatively
inexpensive
pyridine‐
N
‐oxide
directing
group
in
Pd(II)‐catalyzed
site‐selective
γ
‐C(sp
2
)−H,
3
)−H
and
δ
functionalization.
The
functionalization
β
−C−H
bonds
using
bidentate
(DG)
which
operates
through
N,O
‐coordination
mode
has
been
well
documented
literature.
However,
there
exist
rare
reports
dealing
with
remote
sp
/sp
‐
δ‐
C−H
carboxamides
assisted
by
groups
operating
via
‐coordination.
In
this
paper,
scope
DG
was
examined
for
accomplishing
(mono)
arylation
substrates
containing
competitive
C(sp
bonds.
investigation
enabled
to
assemble
a
library
‐oxide‐based
biarylacetamides,
heteroaryl‐based
biaryl
carboxamides,
tricyclic
quinolones,
arylheteroarylmethanes,
biaryl‐based
aliphatic
mono
(
ortho
)
arylated
phenylglycine
derivatives.
general,
derivatives
particular,
arylacetamide,
arylacetic
acid
(2‐aminopyridyl)
motifs
are
medicinally
relevant
classes
compounds.
This
work
assembling
above‐mentioned
types
compounds
group‐aided
γ‐
carboxamides.
