Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(38), P. 8121 - 8127
Published: Sept. 16, 2024
We
developed
an
organophotoredox
catalytic
system
to
facilitate
the
decarboxylative
allylation
coupling
process
concerning
α-amino
acids
and
related
C-terminal
carboxylate
peptides
using
Morita-Baylis-Hillman
adducts
as
allylic
precursors.
This
metal-free
method
operates
under
mild
conditions
is
compatible
with
various
amino
acids.
The
versatility
of
this
protocol,
particularly
in
chemical
biology
research,
has
been
preliminarily
demonstrated
through
ligation
bioactive
peptide
chains.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(20), P. 7983 - 7987
Published: Jan. 1, 2023
An
atom-
and
step-economical,
efficient
eco-friendly
method
for
constructing
naphthoselenazol-2-amines
through
a
visible-light
photocatalytic
multi-component
reaction
under
aqueous
phase
conditions
is
reported.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(20), P. 7971 - 7977
Published: Jan. 1, 2023
Alkyl
diacyl
peroxides
were
demonstrated
to
be
efficient
alkylating
reagents
for
the
visible-light-induced
4CzIPN-catalyzed
direct
C–H
alkylation
of
N
-heteroaromatics.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(8), P. 6247 - 6258
Published: April 10, 2024
Aryl-substituted
bicyclo[1.1.1]pentane
(BCP-aryl)
derivatives
represent
the
most
important
bioisosteres
of
biaryl
scaffolds
and
widely
exist
in
numerous
complex
pharmaceutical
molecules.
The
current
synthetic
method
limitations
using
only
tertiary
radical
precursors,
prefunctionalized
heteroarenes,
toxic
transition
metals,
expensive
photocatalysts
make
it
urgent
to
develop
a
more
simple
practical
protocol.
To
confront
enrich
Minisci-type
chemistry,
herein,
we
disclose
photocatalytic
multicomponent
reaction
for
synthesis
various
(halo)alkyl
BCP-aryls
[1.1.1]propellane,
alkyl
halides,
unfunctionalized
heteroarenes
as
starting
materials.
Diverse
kinds
radicals
(primary,
secondary,
carbons)
derived
from
chlorides,
bromides,
fluoroalkyl
iodides
are
very
compatible
this
transformation.
practicability
is
additionally
boosted
by
product
derivatizations
late-stage
functionalization
pharmaceutically
relevant
mechanistic
studies
demonstrate
that
relay
mechanism
initiated
consecutive
photoinduced
electron
transfer
(ConPET)
process
operation.
We
anticipate
methodology
would
act
useful
tool
biaryl-type
drug
derivatives,
ultimately
resulting
great
utility
discovery
program.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
90(4), P. 1683 - 1696
Published: Jan. 17, 2025
In
the
vanguard
of
sustainable
chemistry,
pursuit
efficient
pathways
for
synthesis
alkyl
bicyclo[1.1.1]pentane-heteroaryls
has
captured
attention
scientific
vanguard.
We
herein
report
a
groundbreaking
and
eco-conscious
multicomponent
coupling
reaction
that
paves
way
alkylation
heteroarylation
[1.1.1]propellane,
process
uniquely
enabled
by
photochemical
prowess
an
electron
donor–acceptor
(EDA)
complex.
This
method
is
distinguished
its
minimalist
yet
powerful
approach:
devoid
transition
metals,
additives,
photosensitizers.
Its
universality
further
exemplified
seamless
compatibility
broad
spectrum
halides
heteroarenes
under
standardized
conditions,
heralding
new
era
synthetic
versatility.
The
method's
practicality
underscored
capacity
late-stage
modification
pharmaceuticals,
offering
transformative
tool
enhancement
existing
drug
molecules.
Moreover,
facile
derivatization
synthesized
products
underscores
adaptability
potential
diverse
applications.
Our
mechanistic
studies
have
elucidated
underlying
radical-relay
pathway,
pinpointing
pivotal
role
EDA
complex
in
initiating
transformation.
discovery
not
only
enriches
our
fundamental
understanding
but
also
opens
avenues
strategic
optimization.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(11), P. 1994 - 1998
Published: March 15, 2023
Herein,
we
report
a
mild
and
practical
protocol
for
the
α-perchloroalkyl
β-heteroarylation
of
alkenes
using
available
chloroform
as
dichloromethyl
source
via
α-amino
radical-mediated
halogen-atom
transfer.
Various
substrates
are
compatible
under
reaction
conditions,
providing
corresponding
products
in
moderate
to
good
yields.
This
strategy
gives
an
efficient
convenient
method
introduction
chloroalkyl
motifs
into
N-heteroarenes.
The
control
experiment
demonstrates
that
radical
generated
situ
is
key
intermediate
transformation.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(6), P. 1758 - 1764
Published: Jan. 1, 2024
This
study
describes
an
efficient
and
green
approach
for
the
synthesis
of
potentially
bioactive
pyrrolo[1,2-
a
]quinoxalin-4(5
H
)-ones
with
appreciable
functional
group
tolerance
wide
substrate
scope.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
This
study
describes
a
pioneering
visible-light-induced
phosphine-catalyzed
halogen-atom
transfer
(XAT)
strategy
that
heralds
new
era
in
the
difunctionalization
of
[1.1.1]propellane.
