Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(12)
Опубликована: Окт. 1, 2022
Abstract
An
efficient,
metal‐free
oxidation
method
of
the
N
‐
ortho
C(sp
3
)−H
bond
amide
via
visible‐light
irradiation
has
been
developed.
A
broad
range
imides
can
be
facilely
obtained
at
room
temperature
and
this
protocol
is
showcased
in
gram‐scale
synthesis.
Preliminary
mechanistic
studies
revealed
that
a
hydrogen
atom
transfer
(HAT)
process
was
involved
H
2
O
offered
main
oxygen
source
to
achieve
greener
photochemical
oxidation.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(7), С. 1072 - 1081
Опубликована: Март 17, 2023
Abstract
Being
in
its
infancy,
radical
cross‐coupling
is
highly
efficient
for
C−C
bond
construction,
though
suffers
from
selectivity
problems
and
limited
reaction
types.
New
methodologies
to
realize
selectively
are
desired.
Herein,
an
iron
catalyzed
deconstructive
cyanomethylation
of
unstrained
cyclic
linear
alcohols
with
acetonitrile
has
been
developed
through
cross‐coupling.
The
unprecedented
method
enables
a
ring‐opening
functionalization
cyclohexanols
produce
α‐cyanomethyl
ketones.
Notably,
the
challenging
involves
twice
single
cleavage
β‐scission
alkoxyl
intermediates,
C(
sp
3
)−H
transformation
via
hydrogen
atom
transfer
(HAT)
procedures,
resulting
two
carbon
species
that
process
form
new
)−C(
)
selectively.
α‐arylketo
α‐aryl
substituted
tertiary
can
also
be
applied
as
substrates,
leading
terminal
cyano‐functionalized
products,
ketone
leaving
fragment.
Mechanistically,
procedure
generate
chlorine
in‐situ
formed
intermediate
cycloalkyl
hypochlorite
was
suggested.
magnified
image
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.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(20), С. 13727 - 13732
Опубликована: Май 10, 2024
Although
chemical
methods
for
the
selective
derivatization
of
amino
acid
(AA)
side
chains
in
peptides
and
proteins
are
available,
N-terminal
labeling
is
challenging,
especially
glycine,
which
has
no
chain
at
α-carbon
position.
We
report
here
a
double
activation
glycine's
α-methylene
group
that
allows
this
AA
to
be
differentiated
from
other
19
AAs.
A
condensation
reaction
dibenzoylmethane
with
glycine
results
formation
an
imine,
subsequent
tautomerization
followed
by
intramolecular
cyclization,
leading
fluorescent
pyrrole
ring.
Additionally,
approach
exhibits
compatibility
AAs
possessing
reactive
chains.
Further,
method
pull-down
assays
mixtures
without
prior
knowledge
peptide
distribution.
European Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 21, 2025
Abstract
A
photoredox‐catalyzed
decarboxylative
C(
sp
3
)−H
alkylation
of
glycine
derivatives,
utilizing
(+)/(−)‐camphorsultam
as
a
chiral
auxiliary
and
alkyl
N
‐hydroxyphthalimide
(NHP)
ester
radical
precursor,
has
been
developed,
providing
an
efficient
approach
for
the
stereoselective
synthesis
valuable
enantioenriched
unnatural
α
‐alkylated
amino
acid
derivatives.
The
methodology
operates
under
mild
conditions,
demonstrates
broad
substrate
tolerance,
exhibits
excellent
stereoselectivity.
Preliminary
mechanistic
investigations
indicate
that
reaction
proceeds
via
pathway.
Chemical Communications,
Год журнала:
2023,
Номер
59(85), С. 12783 - 12786
Опубликована: Янв. 1, 2023
A
visible-light-induced
aerobic
oxidative
[2+3]
cycloaddition
reaction
between
glycine
derivatives
and
thiiranes
is
achieved
via
a
cooperative
photoredox
catalysis
iron
catalysis.
Organic Letters,
Год журнала:
2023,
Номер
25(6), С. 928 - 932
Опубликована: Фев. 2, 2023
A
facile
and
efficient
nickel-catalyzed
C-C
bond
cleavage/phosphorylation
of
various
cycloalkyl
hydroperoxides
was
developed.
This
radical
ring-opening
strategy
provided
practical
access
to
structurally
diverse
distal
ketophosphine
oxides
in
one
pot
through
concurrent
C═O/C-P
formation
with
high
atom
economy
under
mild
room
temperature
base-free
conditions.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(16), С. 11924 - 11934
Опубликована: Авг. 10, 2023
A
new
method
for
the
synthesis
of
α-amino
phenylpropanoids
under
blue
light-emitting
diode
irradiation
has
been
developed
through
α-C-H
benzylation
readily
available
N-phenyl
glycine
ester
with
benzyl
oxalates
as
a
coupling
partner
mild
conditions.
range
esters
were
successfully
converted
to
phenylpropanoid
products
in
moderate
good
yields.
The
utility
this
methodology
is
underlined
by
its
application
late-state
modification
natural
products.
