Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(24), С. 4513 - 4519
Опубликована: Окт. 31, 2023
Abstract
An
oxidant‐free
photocatalytic
[2+2+m]
cyclization
of
2‐cyanoaryl
acrylamides
with
2‐bromocarbonyls
is
reported,
enabling
the
assembly
biologically
important
N‐heterocycle‐fused
quinolinones
including
benzo[1,6]naphthyridinones
and
pyrrolo[3,2‐
c
]‐quinolines.
This
protocol
proceeds
through
a
radical
relay
pathway
alkene
difunctionalization
along
an
intramolecular
cyano
insertion
subsequent
site‐specific
functionalization
inert
C(
sp
3
)−H
bond
enabled
by
cyano‐derived
iminyl
radical‐mediated
1,n‐hydrogen
atom
transfer.
Notably,
this
transformation
selectively
formed
two
distinct
C−C
bonds,
one
C−N
bond,
quaternary
carbon
center
in
one‐pot
procedure.
Herein,
we
report
a
visible
light-induced
difluoromethylation
cyclization
and
subsequent
amination-defluorination
reaction.
This
protocol
allows
efficient
to
valuable
3-fluoro-quinolinones
in
moderate
excellent
yields.
A
sequential
difluoromethylation-cyclization-amination-defluorination
mechanism
was
proposed
based
on
study.
Further
density
functional
theory
(DFT)
calculations
revealed
that
the
base
K
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(46), С. 9112 - 9122
Опубликована: Янв. 1, 2023
Organic
thiocyanates
are
valuable
biological
moities
and
drug-building
blocks.
They
can
also
transform
effectively
into
thioethers,
thiols,
alkynyl
thiocarbamates
in
synthetic
chemistry.
With
respect
to
the
merits
of
thiocyanates,
many
chemists
our
research
team
have
developed
diverse
strategies
access
SCN-revised
heterocycles/spirocycles
via
an
effective
radical
cyclization
process.
Hence,
this
review
article
first
describes
importance/application
thiocyanates.
Subsequently,
it
summarizes
reaction
conditions,
substrate
scopes,
plausible
mechanism,
respectively,
excellent
work
stated
above.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
366(1), С. 70 - 76
Опубликована: Ноя. 17, 2023
A
strategy
for
sulfonylation
of
boronic
acids
with
sulfonyl
chlorides
has
been
established
via
Suzuki-type
radical
cross-coupling.
This
approach
allows
the
synthesis
more
than
50
sulfone
examples
enabled
by
photoredox
catalysis
under
visible
light
radiation.
Moreover,
title
reaction
is
applied
in
late-stage
functionalization
bioactive
molecules,
and
further
transformation
resulting
sulfones
into
2-functionalized
sulfones,
borates,
triphenylphosphine
oxide
N-arylcarbazole
can
be
also
achieved.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(24), С. 4513 - 4519
Опубликована: Окт. 31, 2023
Abstract
An
oxidant‐free
photocatalytic
[2+2+m]
cyclization
of
2‐cyanoaryl
acrylamides
with
2‐bromocarbonyls
is
reported,
enabling
the
assembly
biologically
important
N‐heterocycle‐fused
quinolinones
including
benzo[1,6]naphthyridinones
and
pyrrolo[3,2‐
c
]‐quinolines.
This
protocol
proceeds
through
a
radical
relay
pathway
alkene
difunctionalization
along
an
intramolecular
cyano
insertion
subsequent
site‐specific
functionalization
inert
C(
sp
3
)−H
bond
enabled
by
cyano‐derived
iminyl
radical‐mediated
1,n‐hydrogen
atom
transfer.
Notably,
this
transformation
selectively
formed
two
distinct
C−C
bonds,
one
C−N
bond,
quaternary
carbon
center
in
one‐pot
procedure.
