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
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(ii)-catalyzed selective β-C–H functionalization of azobenzene carboxamides
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(13), P. 2689 - 2694
Published: Jan. 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.
Language: Английский
Pd(ii)-catalyzed coupling of C–H bonds of carboxamides with iodoazobenzenes toward modified azobenzenes
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(8), P. 1793 - 1813
Published: Jan. 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
Language: Английский
Fluorene and Fluorenone Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed sp3C−H Functionalization
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(23)
Published: April 17, 2024
Abstract
This
paper
reports
the
construction
of
racemic
and
enantiopure
(D‐
L‐)
fluorene
fluorenone‐based
novel
unnatural
amino
acid
derivatives.
The
Pd(II)‐catalyzed
bidentate
directing
group‐aided
arylation
prochiral
β
‐C(sp
3
)‐H
bonds
in
racemic,
carboxamides
acids
with
iodofluorenes
was
reported.
examples
fluorenone
motifs
containing
comprising
norvaline,
leucine,
phenylalanine,
norleucine,
2‐aminooctanoic
derivatives
having
anti
‐stereochemistry
(with
good
enantiopurity)
accomplished.
bis
fluorenyl
alanine
scaffolds
motif‐containing
non‐
α
‐amino
(aminoalkanoic
acid)
also
Examples
removal
group
(8‐aminoquinoline)
phthalimide‐protecting
present
fluorenyl‐based
have
been
shown.
Accordingly,
motif‐based
esters
free
group‐containing
were
synthesized.
stereochemistry
major
(
)
diastereomers
obtained
via
ascertained
from
X‐ray
structure
a
representative
compound.
Fluorene‐
are
vital
skeletons
materials
medicinal
chemistry
research.
this
work
is
contribution
towards
enriching
library
scaffolds.
Language: Английский
Construction of C5‐Indole Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed β‐C(sp3)‐H Functionalization
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(25)
Published: May 4, 2024
Abstract
We
report
the
construction
of
C5‐indole
unnatural
amino
acid
derivatives
via
diastereoselective
Pd(II)‐catalyzed
prochiral
β
‐C(sp
3
)‐H
arylation
racemic
(DL),
and
enantiopure
L‐
D‐carboxamides
acids
with
5‐iodoindoles.
Independently,
indole‐based
compounds
motifs
are
important
small
molecules
in
organic
synthesis
drug
discovery
research.
This
aimed
to
contribute
enriching
library
derivatives.
The
examples
motif‐installed
comprising
norvaline,
phenylalanine,
leucine,
norleucine,
2‐aminooctanoic
having
anti‐
stereochemistry
was
accomplished.
motif‐containing
non‐
α
‐amino
(aminoalkanoic
acid)
also
reported.
C−H
reactions
carboxamides
5‐iodoindoles
afforded
corresponding
indole
good
diastereoselectivity
(
anti
,
dr
>95
:
5
enantiopurity
er
up
99
1).
Removal
directing
group
(8‐aminoquinoline),
phthalimide
preparation
esters
free
group‐containing
were
shown.
utility
methodology
shown
by
synthesizing
pyrrolidone
peptide
molecules.
major
)
diastereomers
ascertained
from
X‐ray
structure
a
representative
compound.
Language: 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,
Journal Year:
2023,
Volume and Issue:
13(1)
Published: Nov. 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
Language: Английский