Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 4, 2024
Difluoromethylene
and
pyridine
cores
are
very
important
structural
units
in
medicinal
chemistry.
Herein,
we
report
the
development
of
photoredox-catalyzed
ring-opening
1,3-alkoxypyridylation
gem-difluorinated
cyclopropanes
using
4-cyanopyrines
alcohols,
employing
cyclopropane
radical
cations
as
key
intermediate.
The
reaction
exhibits
high
regioselectivity
under
mild
conditions
can
also
be
practiced
on
gram-scale
synthesis,
telescoped
reaction,
late-stage
functionalization
biological
molecules.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(5), P. 1166 - 1172
Published: Jan. 1, 2023
Visible
light-induced
intermolecular
thiolation/pyridylation
of
styrenes
using
a
thiolate-based
EDA
complex
as
bifunctional
reagent
under
mild
conditions
free
photocatalyst,
metal
or
external
redox
agent
is
reported.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
26(7), P. 4199 - 4208
Published: Jan. 1, 2024
A
new
photoelectrocatalytic
mode
permits
the
synthesis
of
polycyclic
pyrimidin-4-ones
through
dehydrogenative
cyclization
malonates
with
unactivated
alkenes.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(13)
Published: Jan. 19, 2024
Abstract
In
modern
organic
chemistry,
harnessing
the
power
of
multicomponent
radical
reactions
presents
both
significant
challenges
and
extraordinary
potential.
This
article
delves
into
this
scientific
frontier
by
addressing
critical
issue
controlling
selectivity
in
such
complex
processes.
We
introduce
a
novel
approach
that
revolves
around
reversible
addition
thiyl
radicals
to
multiple
bonds,
reshaping
landscape
reactions.
The
key
lies
intricate
interplay
between
reversibility
energy
landscapes
governing
C−C
bond
formation
thiol‐yne‐ene
developed
not
only
allows
prioritize
cascade,
dominating
over
alternative
reactions,
but
also
extends
scope
coupling
products
obtained
from
alkenes
alkynes
various
structures
electron
density
distributions,
regardless
their
relative
polarity
difference,
opening
doors
more
versatile
synthetic
possibilities.
present
study,
we
provide
powerful
tool
for
atom‐economical
C−S
formation,
paving
way
efficient
synthesis
molecules.
Carrying
out
our
experimental
computational
studies,
elucidated
fundamental
mechanisms
underlying
cascades,
knowledge
can
be
broadly
applied
field
chemistry.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(11)
Published: Jan. 20, 2024
Abstract
A
practical
and
mild
electrochemical
dehydrogenative
regioselective
cyclization
method
has
been
established
for
the
synthesis
of
4‐pyrrolin‐2‐ones
using
3‐aza‐1,5‐dienes
1,3‐dicarbonyl
compounds
as
substrates.
This
protocol
is
catalyst‐free,
metal‐free,
does
not
require
oxidizing
agents.
It
exhibits
wide
substrate
compatibility
can
be
easily
scaled
up
to
gram
scale.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(13), P. 2058 - 2091
Published: May 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.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(33), P. 6184 - 6188
Published: Aug. 9, 2023
1,3-Functionalized
cyclobutane
structural
motifs
are
ubiquitous
in
natural
products
and
pharmaceuticals.
Photoinduced
alkylation
of
bicyclo[1.1.0]butanes
(BCBs)
offers
a
step-economical
strategy
for
accessing
1,3-functionalized
motifs.
Herein,
we
disclose
general
mild
photocatalytic
protocol
bromoallylation
BCBs
metal,
additive-free
manner
by
using
the
same
photocatalyst,
2-isopropylthioxanthone,
different
catalytic
roles.
Furthermore,
synthetic
utility
these
was
illustrated
synthesis
various
valuable
complex
derivatives.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(3), P. 1703 - 1708
Published: Jan. 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,
Journal Year:
2024,
Volume and Issue:
60(33), P. 4451 - 4454
Published: Jan. 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.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(31)
Published: April 3, 2024
Abstract
Saturated
heterocycles
are
important
class
of
structural
scaffolds
in
small‐molecule
drugs,
natural
products,
and
synthetic
intermediates.
Here,
we
disclosed
a
metal
free,
mild,
scalable
functionalization
saturated
using
vinylarenes
as
linchpin
approach.
Key
to
success
this
transformation
is
the
employing
simple
cheap
benzophenone
hydrogen
atom
transfer
(HAT)
catalyst.
This
operationally
robust
process
was
used
for
making
diverse
functionalized
heterocycles.
Furthermore,
aldehydes,
alkane,
alcohol
have
been
under
optimized
conditions.
The
potential
pharmaceutical
utility
procedure
has
also
demonstrated
by
late‐stage
bioactive
compounds
molecules.
Initial
mechanism
studies
control
experiments
were
performed
elucidate
reactions
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(51)
Published: June 27, 2023
Described
herein
is
a
visible-light
photoredox-catalyzed
regioselective
1,4-hydroalkylation
of
1,3-enynes.
Various
di-
and
tri-substituent
allenes
were
really
accessible
under
the
present
reaction
conditions.
The
photoredox
activation
carbon
nucleophile
to
generate
its
radical
species,
allowing
addition
with
un-activated
enynes.
synthetic
utility
for
protocol
was
demonstrated
by
large-scale
reaction,
as
well
derivatization
allene
product.
