Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(95), P. 13202 - 13205
Published: Jan. 1, 2022
A
silver-catalysed
oxidative
sp2
C-H
alkylation
of
N-heteroarenes
with
ketone-derived
2,3-dihydroquinazolinones
at
room
temperature
is
developed.
The
combination
a
metal
catalyst
and
perdisulfate
oxidant
promotes
the
rarely
explored
thermal
activation
pre-aromatic
2,3-dihydroquinazolinone
to
generate
an
alkyl
radical,
supported
by
mechanistic
studies.
In
addition
broad
scope,
good
functionality
tolerance,
late
stage
functionalization
APIs,
synthesis
novel
Papaverine
analogue,
utilization
N-heteroarene
bond
ketone
as
non-trivial
radical
source
represents
salient
feature
this
method.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(8), P. 3292 - 3296
Published: Jan. 1, 2023
The
semi-heterogeneous
g-C
3
N
4
/NaI
dual
catalytic
system
driven
C–C
bond
formation
between
quinoxalin-2(1
H
)-ones
and
arylhydrazines
under
blue
light
irradiation
is
reported
for
the
first
time.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(94), P. 14029 - 14032
Published: Jan. 1, 2023
With
both
ferrocene
and
air
as
the
redox
catalysts,
for
first
time,
low-cost
natural
ilmenite
(FeTiO3)
was
successfully
used
photocatalytic
bond
formations.
Under
assistance
of
a
traceless
H-bond,
HCHO
methylene
reagent,
variety
imidazo[1,5-a]quinoxalinones
were
semi-heterogeneously
photosynthesized
in
high
yields
with
good
functional
group
compatibility.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(5), P. 1975 - 1981
Published: Jan. 1, 2023
This
study
describes
a
green
and
sustainable
photoinduced
strategy
for
decarboxylative
C–H
(amino)alkylation
of
heteroarenes
with
carboxylic
acids
under
metal-
photosensitizer-free
conditions.
ACS Catalysis,
Journal Year:
2025,
Volume and Issue:
15(3), P. 1635 - 1654
Published: Jan. 15, 2025
Metallaphotoredox
cross
coupling
(MCC)
is
ranking
among
the
most
advanced
synthetic
methodology
as
it
can
access
chemical
space
that
difficult
to
attain
under
conventional
conditions.
Earlier
developed
MCC
mandates
an
independent
transition
metal
catalyst
and
respective
photocatalyst,
thus
constituting
a
dual
catalytic
manifold.
Complementarily,
paradigm-shifting
metallaphotoredox
strategy
capitalizes
on
single
photoreactive
complex
emerging,
which
brings
not
only
operational
simplification
but
also
unexpected
mechanistic
insights.
This
perspective
compiled
recent
advances
in
monocatalytic
couplings
categorized
them
based
ligands
confer
distinct
photoreactivities
various
mechanisms.
To
this
end,
ligand-enabled
oxidative
addition,
transmetalation,
reductive
elimination
other
radical-involving
pathways
were
summarized
with
notable
examples.
In
way,
we
wish
provide
handy
guideline
for
readers
who
are
interested
emerging
field
inspire
more
future
endeavors
MCCs
beyond.
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
145(2), P. 991 - 999
Published: Dec. 30, 2022
Herein,
we
present
a
comprehensive
study
on
the
use
of
N-heterocyclic
carbene
(NHC)-ligated
boryl
radicals
to
enable
C(sp3)–C(sp3)
bond
formation
under
visible-light
irradiation
via
Halogen-Atom
Transfer
(XAT).
The
methodology
relies
an
acridinium
dye
generate
boron-centered
from
corresponding
NHC-ligated
boranes
single-electron
transfer
(SET)
and
deprotonation.
These
subsequently
engage
with
alkyl
halides
in
XAT
step,
delivering
desired
nucleophilic
radicals.
strategy
is
very
mild
accommodates
broad
scope
halides,
including
medicinally
relevant
compounds
biologically
active
molecules.
key
role
operative
reaction
mechanism
has
been
elucidated
through
combination
experimental,
spectroscopic,
computational
studies.
This
stands
as
significant
advancement
chemistry
radicals,
which
had
long
restricted
radical
reductions,
enabling
C–C
photoredox
conditions.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(13)
Published: Feb. 1, 2023
A
method
for
direct
access
to
enantioenriched
benzylic
amides
and
carbamate-protected
primary
benzylamines
by
C-H
functionalization
is
reported.
The
substrate
used
as
limiting
reagent
with
only
a
small
excess
of
the
unactivated
amide
or
carbamate
nucleophile.
enantioselective
intermolecular
dehydrogenative
C-N
bond
formation
enabled
combination
chiral
copper
catalyst,
photocatalyst,
an
oxidant,
it
takes
place
under
mild
conditions,
which
allow
broad
scope.
compatible
late-stage
functionalization,
provides
easy
15
N-labeled
amines
starting
from
cheap
NH4
Cl.
Molecules,
Journal Year:
2023,
Volume and Issue:
28(16), P. 6127 - 6127
Published: Aug. 18, 2023
The
functionalisation
of
C–H
bonds
has
been
an
enormous
achievement
in
synthetic
methodology,
enabling
new
retrosynthetic
disconnections
and
affording
simple
equivalents
for
synthons.
Hydrogen
atom
transfer
(HAT)
is
a
key
method
forming
alkyl
radicals
from
substrates.
Classic
reactions,
including
the
Barton
nitrite
ester
reaction
Hofmann–Löffler–Freytag
reaction,
among
others,
provided
early
examples
HAT.
However,
recent
developments
photoredox
catalysis
electrochemistry
have
made
HAT
powerful
tool
capable
introducing
wide
range
functional
groups
into
bonds.
Moreover,
greater
mechanistic
insights
stimulated
development
increasingly
site-selective
protocols.
Site-selectivity
can
be
achieved
through
tuning
electron
density
at
certain
using
additives,
judicious
choice
reagent,
solvent
system.
Herein,
we
describe
latest
methods
functionalizing
C–H/Si–H/Ge–H
indirect
between
2018–2023,
as
well
critical
discussion
reagents,
aspects,
substrate
scopes,
background
contexts
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(9), P. 1441 - 1446
Published: Feb. 23, 2023
A
visible-light-photocatalyzed
1,2-arylalkylation
of
N-(arylsulfonyl)acrylamides
with
ketone-based
dihydroquinazolinones
is
described.
The
formal
C-C
bond
cleavage
aliphatic
ketones
unified
tandem
radical
alkylation/1,4-aryl
migration/desulfonylation
to
forge
two
different
types
vicinal
bonds
and
construct
an
all-carbon
quaternary
α-stereocenter,
thus
enhancing
the
carbogenic
complexity
tolerating
diverse
functionalities.
Additional
telescopic
synthesis
product
diversification,
this
method
features
a
dicarbofunctionalization
conjugated
nucleophilic
alkyl
precursor
(dihydroquinazolinone)
utilizing
oxygen
as
green
oxidant
at
ambient
temperature.
