Organic Letters,
Год журнала:
2024,
Номер
26(25), С. 5323 - 5328
Опубликована: Июнь 17, 2024
Amino
acids
and
aromatic
nitrogen
heterocycles
are
widely
used
in
pharmaceuticals.
Herein,
we
present
an
effective
visible-light-driven
thiobenzoic
acid
(TBA)-catalyzed
decyanative
C(sp3)–H
heteroarylation
of
glycine
derivatives.
This
process
occurs
under
mild
straightforward
conditions,
affording
a
range
valuable
yet
challenging-to-obtain
α-heteroaryl
amino
Moreover,
this
organocatalytic
C(sp3)–C(sp2)
bond
formation
reaction
is
applicable
to
the
late-stage
modification
various
short
peptides.
Organic Letters,
Год журнала:
2022,
Номер
24(41), С. 7677 - 7684
Опубликована: Окт. 10, 2022
A
general
and
mild
strategy
involving
three-component
carboarylation
of
unactivated
alkenes
with
protic
C(sp3)–H
feedstocks
via
photoredox
catalysis
was
reported.
This
catalytic
system
is
compatible
a
broad
range
alkenes,
cyano-substituted
arenes,
diverse
feedstocks.
The
synthetic
value
this
protocol
demonstrated
by
the
late-stage
functionalization
complex
molecules
synthesis
antiallergies
including
pheniramine,
chlorpheniramine,
brompheniramine.
Green Chemistry,
Год журнала:
2022,
Номер
24(3), С. 1342 - 1349
Опубликована: Янв. 1, 2022
Electrocatalysis
for
the
controllable
coupling
of
thiols
with
DCE
was
achieved
to
generate
value-added
β-chloro-tethered
sulfur
compounds
in
batch
and
flow.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(13), С. 2058 - 2091
Опубликована: Май 17, 2023
Abstract
Decyanation
is
an
important
process
in
the
synthesis
of
aromatic
molecules
studies
pharmaceutical
research,
medical
and
materials
sciences.
In
late‐stage
modifications
privileged
carbo/heterocyclic
scaffolds,
radical‐type
decyanation
techniques
have
been
devised
to
date.
As
a
result,
chemistry
cyano‐involved
conversions,
hotly
debated
subject
over
past
few
decades,
has
advanced
significantly.
The
cyano
group
(CN),
on
other
hand,
rarely
acknowledged
as
good
reaction
site
due
its
thermodynamic
robustness.
most
recent
advancements
catalytic
radical
protocols
that
CN
behaved
leaving
made
are
surveyed
this
article.
Following
introduction
number
different
modes,
reactions
used
activate
C−CN
bonds
primarily
categorized,
text
herein
divided
into
three
groups:
(1)
photo‐catalyzed
transformations,
(2)
electro‐catalyzed
(3)
transition‐metal‐catalyzed
or
metal‐free
transformations.
With
emphasis
systems
synthetic
applications
bond
activation,
review
will
provide
readers
with
overview
reactions.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(12), С. 1399 - 1406
Опубликована: Фев. 29, 2024
Comprehensive
Summary
A
general
and
convenient
photoredox‐catalyzed
acylation
alkylcyanation
of
MBH
acetates
has
been
established,
enabling
the
assembly
C(sp
2
)–C(sp
3
)
bond
by
a
nitrogen‐centered
radical
strategy
for
synthesis
trisubstituted
alkenes
in
moderate
to
excellent
chemical
yields
(48
examples
total).
The
reaction
with
acyl
(indanone)
oxime
esters
afforded
containing
1,4‐dicarbonyl
groups.
Interestingly,
use
Eosin
Y
as
photocatalyst
catalytic
system
resulted
formation
distal
cyano
group‐anchored
via
deconstructive
functionalization
cycloketone
esters.
Notably,
these
resulting
compounds
could
be
applied
late‐stage
transformations,
providing
important
methods
dihydropyridazin‐3(2
H
)‐one.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(37)
Опубликована: Июнь 20, 2024
Abstract
Here,
we
report
CdS
quantum
dot
(QD)
gels,
a
three‐dimensional
network
of
interconnected
QDs,
as
new
type
direct
hydrogen
atom
transfer
(d‐HAT)
photocatalyst
for
C−H
activation.
We
discovered
that
the
photoexcited
QD
gel
could
generate
various
neutral
radicals,
including
α‐amido,
heterocyclic,
acyl,
and
benzylic
from
their
corresponding
stable
molecular
substrates,
amides,
thio/ethers,
aldehydes,
compounds.
Its
activation
ability
imparts
broad
substrate
reaction
scope.
The
mechanistic
study
reveals
this
reactivity
is
intrinsic
to
materials,
radical
generation
did
not
proceed
via
conventional
sequential
electron
proton
pathway.
Instead,
bonds
are
activated
by
d‐HAT
mechanism.
This
mechanism
supported
linear
correlation
between
logarithm
bond
rate
constant
dissociation
energy
(BDE)
with
Brønsted
slope
α
=0.5.
Our
findings
expand
currently
limited
photocatalysis
toolbox
provide
possibilities
photocatalytic
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(3), С. 1703 - 1708
Опубликована: Янв. 16, 2024
Visible-light-induced
three-component
1,2-alkylpyridylation
of
alkenes
with
unactivated
alkyl
iodides
and
aryl
cyanides
is
reported
via
a
photocatalytic
halogen-atom
transfer
(XAT)
strategy.
This
metal-free
protocol
utilizes
readily
available
tertiary
alkylamine
as
the
terminal
reductant
to
smoothly
convert
into
corresponding
carbon
radical
species.
The
reaction
features
broad
substrate
scope,
excellent
functional
group
tolerance,
high
efficiency,
mild
conditions.
practicability
this
methodology
further
demonstrated
in
late-stage
difunctionalization
bioactive
molecules.
Chemical Communications,
Год журнала:
2024,
Номер
60(33), С. 4451 - 4454
Опубликована: Янв. 1, 2024
Photocatalytic
α-C(sp
3
)–H
pyridination
of
N
-arylglycine
derivatives
and
-arylamines
with
cyanopyridines
was
developed
through
radical–radical
cross-coupling
under
redox-neutral
conditions.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 2, 2025
A
photoredox-catalyzed
radical
cascade
cyclization
of
N-(o-cyanobiaryl)acrylamides
with
sulfonyl
chlorides
for
the
construction
sulfonyl-containing
pyrido[4,3,2-gh]phenanthridines
has
been
disclosed.
The
developed
synthetic
tool
tolerates
a
broad
range
to
undergo
sequence,
including
addition,
nitrile
insertion,
and
cyclization.
