Picolinamide-assisted ortho-C–H functionalization of pyrenylglycine derivatives using aryl iodides
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.
Language: Английский
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,
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.
Language: Английский
Construction of β‐Phenylalanine Derivatives through Pd‐Catalyzed, C(sp2)−H (ortho) Functionalization
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(29)
Published: June 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.
Language: 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,
Journal Year:
2023,
Volume and Issue:
55(21), P. 3535 - 3567
Published: March 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.
Language: Английский
Recent Advances in C–H Functionalization of Pyrenes
Chemistry,
Journal Year:
2023,
Volume and Issue:
5(4), P. 2713 - 2755
Published: Dec. 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.
Language: Английский
Phenylglycinol Derived Chemistry
Elsevier eBooks,
Journal Year:
2023,
Volume and Issue:
unknown, P. 606 - 637
Published: July 20, 2023
Language: Английский
Pd-Catalyzed Remote δ-C(sp2)–H Functionalization in Phenylalaninol: Expanding the Library of Phenylalaninols
Synthesis,
Journal Year:
2023,
Volume and Issue:
55(24), P. 4113 - 4144
Published: Aug. 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.
Language: Английский