Pd‐Catalyzed Arylation and Benzylation of Tyrosine at the δ−C(sp2)−H and C(2) Positions: Expanding the Library of Unnatural Tyrosines
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.
Язык: Английский
Picolinamide-assisted ortho-C–H functionalization of pyrenylglycine derivatives using aryl iodides
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.
Язык: Английский
Construction of β‐Phenylalanine Derivatives through Pd‐Catalyzed, C(sp2)−H (ortho) Functionalization
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.
Язык: Английский
Pd(ii)-catalyzed coupling of C–H bonds of carboxamides with iodoazobenzenes toward modified azobenzenes
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
Язык: Английский
Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation, Alkylation, Benzylation, and Methoxylation of Carbazole-3-carboxamides toward C2,C3,C4-Functionalized Carbazoles
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.
Язык: Английский
Recent Advances in C–H Functionalization of Pyrenes
Chemistry,
Год журнала:
2023,
Номер
5(4), С. 2713 - 2755
Опубликована: Дек. 11, 2023
In
recent
years,
transition
metal-catalyzed
C–H
activation
and
site-selective
functionalization
have
been
considered
to
be
valuable
synthetic
tactics
functionalize
organic
compounds
containing
multiple
bonds.
Pyrene
is
one
of
the
privileged
notorious
polycyclic
aromatic
hydrocarbons.
its
derivatives
found
applications
in
various
branches
chemical
sciences,
including
chemistry,
biology,
supramolecular
material
sciences.
Given
importance
pyrene
derivatives,
several
classical
methods,
method,
developed
for
synthesizing
modified
scaffolds.
This
review
attempts
cover
developments
area
pertaining
modification
motif
through
process
bonds
present
motif,
leading
functionalized
pyrenes.
Язык: Английский
Palladium-catalysed α and β C–H allylation of aryl alkenes
Yilei Liao,
Xiandie Zhang,
Xiaoli Li
и другие.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(12), С. 3341 - 3347
Опубликована: Янв. 1, 2024
This
work
focuses
on
α
and
β
C–H
allylation
of
aryl
alkenes
using
allyl
carbonates
to
produce
linear
branched
1,4-dienes
enabled
by
chelation-assistance
pyridine-2-carboxamide,
which
is
simply
performed
with
Pd(OAc)
2
/AcOH
in
ethanol.
Язык: Английский
Utility of 4‐Amino‐2,1,3‐benzothiadiazole Directing Group in the Pd(II)‐catalyzed Arylation of γ‐C−H Bonds of Carboxamides and β‐C‐H Bonds of Amino Acid Carboxamides
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
Язык: Английский
Pd-Catalyzed Remote δ-C(sp2)–H Functionalization in Phenylalaninol: Expanding the Library of Phenylalaninols
Synthesis,
Год журнала:
2023,
Номер
55(24), С. 4113 - 4144
Опубликована: Авг. 2, 2023
Abstract
We
report
the
Pd(II)-catalyzed,
picolinamide-directed
δ-C(sp2)–H
(ortho)
functionalization
of
phenylalaninol
scaffolds.
Assembling
δ-C–H
arylated,
alkylated,
benzylated,
alkenylated,
brominated,
and
iodinated
scaffolds
was
accomplished.
The
arylation
reaction
occurred
under
neat
conditions.
Hydrolysis
picolinamide
moiety
synthetic
utility
arylated
substrates
were
explored.
have
also
shown
preparation
some
modified
Matijin–Su
(aurantiamide)
derivatives
using
bis
compounds
obtained
from
(Matijin–Su
is
an
anti-HBV
agent
possessing
unit).
Considering
importance
phenylalaninols,
this
work
contributes
to
expanding
library
demonstrates
substrate
scope
development
in
remote
reactions.
Язык: Английский
Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls
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
Язык: Английский