Green Chemistry,
Год журнала:
2023,
Номер
25(17), С. 6733 - 6738
Опубликована: Янв. 1, 2023
A
metal
free,
visible-light
driven
α-C(sp
3
)−H
gem-difluoroallylation
of
glycine
derivatives
with
CF
-alkenes
and
1,3-enynes
is
presented
under
redox-neutral
conditions
good
yields
excellent
functional
group
compatibility.
Organic Letters,
Год журнала:
2025,
Номер
27(4), С. 1072 - 1077
Опубликована: Янв. 18, 2025
A
Cu(I)
photoredox-enabled
reaction
that
selectively
incorporates
a
difluoroalkyl
group
into
N-aryl
glycine
derivatives
has
been
established.
Using
bench-stable
[Ph3PCF2H]+Br-
salt,
the
-CF2H
could
be
installed
either
directly
on
α-carbon
of
backbone
or
in
three-component
fashion
using
an
alkene
as
bridge.
series
have
evaluated,
providing
access
to
diverse
unnatural
amino
esters
and
dipeptides
with
-CHF2
unit.
The
studies
compatibility
other
perfluorinated
alkyl
radical
precursors
showed
selectivity
direct
α-coupling
is
closely
associated
electronic
property
radical,
while
works
well
most
cases.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(6), С. 4056 - 4066
Опубликована: Март 7, 2024
An
organo-photoredox
catalyzed
gem-difluoroallylation
of
glycine
with
α-trifluoromethyl
alkenes
via
direct
C(sp3)–H
functionalization
and
C–F
bond
activation
has
been
described.
As
a
consequence,
broad
range
gem-difluoroalkene-containing
unnatural
amino
acids
are
afforded
in
moderate
to
excellent
yields.
This
reaction
exhibits
multiple
merits
such
as
readily
available
starting
materials,
substrate
scope,
mild
conditions.
The
feasibility
this
highlighted
by
the
late-stage
modification
several
peptides
well
improved
vitro
antifungal
activity
compound
3v
toward
Valsa
mali
compared
that
commercial
azoxystrobin.
Abstract
Sulfur‐containing
amino
acids
and
peptides
play
critical
roles
in
organisms.
Thiol‐ene
reactions
between
the
thiol
residues
of
L
‐cysteine
alkenyl
fragments
designed
coupling
partners
serve
as
primary
tools
for
constructing
C─S
bonds
synthesis
unnatural
sulfur‐containing
acid
derivatives.
These
are
favored
due
to
preference
hydrogen
transfer
from
β‐sulfanyl
carbon
radical
intermediates.
In
this
paper,
study
proposes
utilizing
carbon‐centered
radicals
stabilized
by
capto‐dative
effect,
generated
under
photocatalytic
conditions
N
–aryl
glycine
The
aim
is
compete
with
hydrogen,
enabling
C─C
bond
formation
radicals.
This
protocol
robust
presence
air
water,
offers
significant
potential
a
modular
efficient
platform
synthesizing
modifying
peptides,
particularly
abundant
disulfides
styrenes.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(41), С. 8364 - 8371
Опубликована: Янв. 1, 2023
A
Ce(III)-catalyzed,
visible-light
induced
aerobic
oxidative
dehydrogenative
coupling
reaction
between
glycine
derivatives
and
electron-rich
arenes
is
disclosed.
The
protocol
proceeds
efficiently
under
mild
conditions,
providing
an
efficient
method
for
the
rapid
synthesis
of
α-arylglycine
without
need
external
photosensitizer
additional
oxidant.
Moreover,
this
could
be
performed
on
a
5
mmol
scale,
obvious
reduction
efficiency.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(9), С. 2301 - 2309
Опубликована: Янв. 1, 2023
A
Cu-catalysed
and
ligand-controlled
glycine
ligation
method
is
developed
for
the
modular
selective
synthesis
of
diverse
CF
3
-containing
amino
acids
dipeptides.
Organic Letters,
Год журнала:
2023,
Номер
25(23), С. 4329 - 4334
Опубликована: Июнь 1, 2023
An
inexpensive
iron-catalyzed
alkoxyl
radical-induced
C–C
bond
cleavage/gem-difluoroalkylation
cascade
is
presented.
Regulated
by
the
structure
of
radical
precursors,
fluorinated
distal
diketones
were
synthesized
through
a
ring-opening
strategy
and
difluoroalkylated
medium-sized
lactones
macrolactones
constructed
via
ring-expansion
strategy.
Both
protocols
proceeded
under
mild
redox
neutral
conditions
with
broad
substrate
scope
good
functional
group
compatibility.
Chemical Communications,
Год журнала:
2023,
Номер
60(1), С. 106 - 109
Опубликована: Ноя. 24, 2023
Organophotocatalytic
cascade
cross-dehydrogenative-coupling/cyclization
reaction
of
o-hydroxyarylenaminones
with
α-amino
acid
derivatives
for
the
construction
α-chromone
substituted
was
developed.
Various
N-arylglycine
esters,
amides
and
dipeptides
underwent
cyclization
well
to
afford
corresponding
3-aminoalkyl
chromones
in
good
excellent
yields.
This
approach
consists
visible-light-promoted
oxidation
derivatives,
Mannich
reaction,
intramolecular
nucleophilic
under
acidic
conditions,
features
a
wide
scope,
simple
operation
mild
which
may
have
potential
be
used
synthesis
bioactive
molecules.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
10(2), С. 382 - 387
Опубликована: Ноя. 25, 2022
An
iron-catalysed
and
ligand-controlled
selective
α-C–H
alkylation
of
N
-aryl
glycinates
is
established
with
γ,δ-unsaturated
oxime
esters
as
the
reagent.
This
method
provides
a
facile
synthetic
approach
to
obtain
pyrroline-containing
amino
acids.
