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
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.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
21(4), С. 673 - 699
Опубликована: Дек. 22, 2022
Over
the
past
decades,
reactions
involving
C-H
functionalization
have
become
a
hot
theme
in
organic
transformations
because
they
lot
of
potential
for
streamlined
synthesis
complex
molecules.
C(sp3)-H
bonds
are
present
most
species.
Since
molecules
massive
significance
various
aspects
life,
exploitation
and
hold
enormous
importance.
In
recent
years,
first-row
transition
metal-catalyzed
direct
selective
has
emerged
as
simple
environmentally
friendly
synthetic
method
due
to
its
low
cost,
unique
reactivity
profiles
easy
availability.
Therefore,
research
advancements
being
made
conceive
catalytic
systems
that
foster
under
benign
reaction
conditions.
Cobalt-based
catalysts
offer
mild
convenient
conditions
at
reasonable
expense
compared
conventional
2nd
3rd-row
metal
catalysts.
Consequently,
probing
Co-based
is
one
topics
from
outlook
an
chemist.
This
review
primarily
focuses
on
literature
2018
2022
sheds
light
substrate
scope,
selectivity,
benefits
limitations
cobalt
transformations.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(13), С. 2689 - 2694
Опубликована: Янв. 1, 2023
We
report
a
Pd(II)-catalyzed
bidentate
directing
group
8-aminoquinoline-aided,
site-selective
β-C-H
functionalization
protocol
for
assembling
modified
azobenzene
carboxamides.
Considering
the
importance
of
azobenzenes
in
chemical
sciences,
this
paper
reports
new
route
enriching
library
motifs.
Synthesis,
Год журнала:
2022,
Номер
54(18), С. 4059 - 4094
Опубликована: Апрель 20, 2022
Abstract
In
this
paper,
we
report
the
Pd(II)-catalyzed,
picolinamide
DG-aided
sp2
γ-C–H
functionalization
and
expansion
of
library
enantiopure
α-methylbenzylamine
phenylglycinol
scaffolds.
We
have
shown
synthesis
a
wide
range
racemic
ortho-C–H
arylated,
alkylated,
brominated,
iodinated
Various
R
S
(chiral)
functionalized
scaffolds
were
synthesized
with
good
enantiopurities.
Racemic
derivatives
are
important
building
blocks
in
organic
medicinal
chemistry.
Accordingly,
work
contributes
to
libraries
motifs
substrate
scope
development
through
Pd(II)-catalyzed
bidentate
directing
group
picolinamide-aided
site-selective
C–H
activation
method.
Chemistry - An Asian Journal,
Год журнала:
2023,
Номер
19(5)
Опубликована: Дек. 27, 2023
Abstract
The
use
of
iron
as
a
core
metal
in
catalysis
has
become
research
topic
interest
over
the
last
few
decades.
reasons
are
clear.
Iron
is
most
abundant
transition
on
Earth's
crust
and
it
widely
distributed
across
world.
It
been
extracted
processed
since
dawn
civilization.
All
these
features
render
noncontaminant,
biocompatible,
nontoxic,
inexpensive
therefore
constitutes
perfect
candidate
to
replace
noble
metals
(rhodium,
palladium,
platinum,
iridium,
etc.).
Moreover,
direct
C−H
functionalization
one
efficient
strategies
by
which
introduce
new
functional
groups
into
small
organic
molecules.
majority
compounds
contain
C(sp
3
)−H
bonds.
Given
enormous
importance
molecules
so
many
aspects
existence,
utilization
bioactivity
bonds
utmost
importance.
This
review
sheds
light
substrate
scope,
selectivity,
benefits,
limitations
catalysts
for
bond
activations.
An
overview
activation
protocols
summarized
herein
up
2022.
Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(9)
Опубликована: Авг. 8, 2022
Abstract
This
paper
reports
the
synthesis
of
enantiopure
aryl
alkyl
ethers
via
Pd(II)‐catalyzed
picolinamide‐aided
γ
‐C(sp
2
)−H
alkoxylation
various
α
‐alkylbenzylamine
derivatives
using
alcohols.
Enantiopure
‐methylbenzylamines
and
amino
alcohol
substrates
such
as
2‐amino‐2‐phenylethanol
(phenylglycinol)
3‐amino‐3‐phenylpropanol
were
subjected
to
(etherification)
with
alcohols
PIDA.
‐Alkylbenzylamines
phenylglycinols
are
valuable
building
blocks
in
organic
medicinal
chemistry
research
areas.
Accordingly,
this
work
has
enabled
assembling
ortho
‐alkoxylated
‐methylbenzylamine
containing
ether
functionality.
We
have
shown
utility
for
‐methylbenzylamine‐based
sulfamoylcarbamates
carboxamides
which
structurally
related
bio‐active
compounds
known
literature.
demonstrates
substrate
scope
elaboration
C−H
functionalization
etherification
through
C−O
bond‐forming
process
functionality
‐alkylbenzylamines.
Chemical Communications,
Год журнала:
2022,
Номер
58(93), С. 12967 - 12970
Опубликована: Янв. 1, 2022
Azobenzene-based
unnatural
amino
acid
motifs
were
constructed
via
the
Pd(
ii
)-catalyzed
diastereoselective
β-C(sp
3
)–H
arylation
and
Mills
azo
coupling
tactics.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(8), С. 1793 - 1813
Опубликована: Янв. 1, 2023
In
this
paper,
we
report
a
synthetic
protocol
for
the
construction
of
biaryl
motif-based
or
π-extended
azobenzene
and
alkylated
derivatives
via
Pd(II)-catalyzed
bidentate
directing
group
(DG)-aided
C-H
activation
functionalization
strategy.
past,
synthesis
azobenzenes
was
accomplished
through
traditional
cross-coupling
reaction
involving
organometallic
reagents
aryl
halides
equivalent
coupling
partners.
We
have
shown
direct
bonds
aromatic/aliphatic
carboxamides
(possessing
DG)
with
iodoazobenzenes
as
partners
DG-aided,
site-selective
method.
Azobenzene-containing
compounds
are
versatile
class
photo-responsive
molecules
that
found
applications
across
branches
chemical,
biological
materials
sciences
prevalent
in
medicinally
relevant
molecules.
Accordingly,
new
functionalized
azobenzene-based
scaffolds
has
been
an
attractive
topic
research.
Although
classical
methods
efficient,
they
need
pre-functionalized
starting
materials.
This
Pd(II)-catalyzed,
group-aided
arylation
aromatic
aliphatic
using
iodoazobenzene
partner
affording
is
additional
route
also
contribution
towards
enriching
library
modified
azobenzenes.
photoswitching
properties
representative
synthesized
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.