Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(40), P. 7394 - 7399
Published: Oct. 4, 2022
Functionalized
pyridine
and
quinoline
rings
are
important
components
of
numerous
bioactive
molecules
natural
products;
however,
diversification
these
often
requires
de
novo
heterocycle
ring
synthesis
or
demanding
reaction
conditions.
We
report
a
method
for
desulfinative
alkylation
N-methoxide
salts
that
operates
under
both
photocatalytic
electrostatic
electron
donor-acceptor-mediated
pathways.
Unlike
most
EDA-mediated
processes,
this
in
the
absence
light
with
desulfination
donor
compound.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(45), P. 8116 - 8120
Published: Nov. 8, 2023
Hantzsch
esters
(HEs)
are
widely
recognized
as
sources
of
hydride
ions
(H-)
and
sacrificial
electron
donors
in
their
ground
state.
Here,
we
report
the
application
HE
a
mediator
[2π+2σ]
cycloaddition
bicyclo[1.1.0]butanes
(BCBs)
with
alkenes
under
photo
conditions.
Through
this
strategy,
various
substituted
bicyclo[2.1.1]hexanes
can
be
efficiently
prepared.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
26(12), P. 7331 - 7336
Published: Jan. 1, 2024
A
novel
photocatalytic
acylation
strategy
was
developed
harnessing
tetrabutylammonium
decatungstate
(TBADT)
as
a
hydrogen
atom
transfer
(HAT)
photocatalyst
to
facilitate
the
direct
coupling
of
aldehydes
with
N-heterocycles
at
ambient
temperature.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(24)
Published: April 15, 2023
Abstract
1‐Aryl‐substituted
bicyclo[1.1.1]pentanes
(BCPs)
are
an
important
class
of
BCP
derivatives
with
widespread
application
in
drug
development.
Most
syntheses
these
materials
require
multiple
chemical
steps
via
electrophiles
or
nucleophiles
derived
from
[1.1.1]propellane.
Although
one‐step,
multicomponent
radical
cross‐coupling
reactions
could
provide
a
more
sustainable
and
rapid
route
to
access
diverse
heteroarylated
BCPs,
current
approaches
limited
tertiary
alkyl
radicals,
leading
decrease
their
practical
value.
In
this
study,
conceptually
different
approach
enabled
by
heteroarylation
[1.1.1]propellane
functionalized
BCPs
is
described.
Importantly,
protocol
compatible
primary‐,
secondary‐,
aliphatic
as
well
various
fluoroalkyl
sources,
thus
enabling
library
generation
sought‐after
for
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(4), P. 2543 - 2549
Published: Feb. 7, 2023
We
conceptualized
a
novel
disconnection
approach
for
the
synthesis
of
fused
tetrahydroquinolines
that
exploits
visible
light-mediated
radical
(4
+
2)
annulation
between
alkyl
N-(acyloxy)phthalimides
and
N-substituted
maleimides
in
presence
DIPEA
as
an
additive.
The
reaction
proceeds
through
formation
photoactivated
electron
donor-acceptor
complex
NHPI
esters
DIPEA,
final
were
obtained
complete
regioselective
fashion.
methodology
features
broad
scope
good
functional
group
tolerance
operates
under
metal-
catalyst-free
conditions.
Detailed
mechanistic
investigations
including
density
theory
studies
provide
insight
into
pathway.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(12), P. 8508 - 8519
Published: Feb. 21, 2024
Tricomponent
cobalt(salen)-catalyzed
carbofunctionalization
of
unsaturated
substrates
by
radical-polar
crossover
has
the
potential
to
streamline
access
broad
classes
heteroatom-functionalized
synthetic
targets,
yet
reaction
platform
remained
elusive,
despite
well-developed
analogous
hydrofunctionalizations
mediated
high-valent
alkylcobalt
intermediates.
We
report
herein
development
a
cobalt(salen)
catalytic
system
that
enables
carbofunctionalization.
The
entails
tricomponent
decarboxylative
1,4-carboamination
dienes
and
provides
direct
route
aromatic
allylic
amines
obviating
preformed
allylation
reagents
protection
oxidation-sensitive
amines.
merges
acridine
photocatalysis
with
regioselective
1,4-carbofunctionalization
facilitates
radical
polar
phases
coupling
process,
revealing
critical
roles
reactants,
as
well
ligand
effects
nature
formal
species
on
chemo-
regioselectivity.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(14), P. 2843 - 2846
Published: Jan. 22, 2024
A
route
toward
heterocycle-functionalized
bicyclo[3.1.1]heptanes
(BCHeps)
and
aza-bicyclo[3.1.1]heptanes
(aza-BCHeps)
has
been
developed,
using
mild,
photocatalytic
Minisci-like
conditions
to
introduce
various
heterocycles
at
the
bridgehead
position
from
readily
available
N-hydroxyphthalimide
esters
of
corresponding
carboxylic
acids.
This
chemistry
enables
access
BCHep-containing
structures
that
are
highly
relevant
in
medicinal
research
as
potential
bioisosteres
meta-substituted
arenes
pyridines.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(43), P. 7961 - 7966
Published: Oct. 24, 2022
The
photocatalyst-free
electron
donor–acceptor
(EDA)
complex
photochemistry
was
deemed
to
expand
the
potential
of
photodriven
radical
chemistry.
Here,
we
report
a
cross-coupling
reaction
thianthrenium
salt
functionalized
arenes
and
sodium
sulfinates
via
photopromoted
single
transfer
(SET)
process
an
EDA
complex.
A
series
biarylsulfones
were
obtained
with
high
site-selectivity
reactivity.
This
mild
practical
could
be
applied
on
bioactive
DNA-encoded
molecules.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(43)
Published: Aug. 25, 2022
The
intermediate
oxidation
state
of
sulfoxides
is
central
to
the
plethora
their
applications
in
chemistry
and
medicine,
yet
it
presents
challenges
for
an
efficient
synthetic
access,
limiting
structural
diversity
currently
available
sulfoxides.
Here,
we
report
a
data-guided
development
direct
decarboxylative
sulfinylation
that
enables
previously
inaccessible
functional
group
interconversion
carboxylic
acids
reaction
with
sulfinates.
Given
broad
availability
growing
potential
sulfinates,
poised
improve
synthetically
accessible
facilitated
by
kinetically
favored
sulfoxide
formation
from
sulfinyl
sulfones,
despite
strong
thermodynamic
preference
sulfone
formation,
unveiling
unknown
chemoselective
radicalophilic
reactivity.
JACS Au,
Journal Year:
2023,
Volume and Issue:
3(3), P. 813 - 822
Published: Feb. 16, 2023
Triazoles
have
major
roles
in
chemistry,
medicine,
and
materials
science,
as
centrally
important
heterocyclic
motifs
bioisosteric
replacements
for
amides,
carboxylic
acids,
other
carbonyl
groups,
well
some
of
the
most
widely
used
linkers
click
chemistry.
Yet,
chemical
space
molecular
diversity
triazoles
remains
limited
by
accessibility
synthetically
challenging
organoazides,
thereby
requiring
preinstallation
azide
precursors
restricting
triazole
applications.
We
report
herein
a
photocatalytic,
tricomponent
decarboxylative
triazolation
reaction
that
first
time
enables
direct
conversion
acids
to
single-step,
triple
catalytic
coupling
with
alkynes
simple
reagent.
Data-guided
inquiry
accessible
indicates
transformation
can
improve
access
structural
complexity
triazoles.
Experimental
studies
demonstrate
broad
scope
synthetic
method
includes
variety
acid,
polymer,
peptide
substrates.
When
performed
absence
alkynes,
also
be
obviating
preactivation
specialized
reagents
providing
two-pronged
approach
C–N
bond-forming
functional
group
interconversions.
