Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 17, 2025
Comprehensive
Summary
A
practical
photocatalytic
annulation‐biselenylation
strategy
has
been
developed
for
the
efficient
synthesis
of
biselenium‐substituted
1‐indanones
(38
examples
in
total)
with
generally
good
yields
(up
to
95%)
and
excellent
stereoselectivity
(>19
:
1
Z
/
E
ratio)
by
employing
enynones
diaryl
selenides
as
starting
materials
under
photosensitizer‐free
conditions.
The
reaction
mechanism
involves
a
cascade
process
comprising
homolytic
cleavage,
radical
addition,
5‐
exo
‐
dig
cyclization,
capture,
enabling
sequential
formation
multiple
bonds,
such
C(sp
3
)‐Se,
)‐C(sp
2
),
)‐Se
rapidly
construct
molecular
complexity.
Notably,
this
approach
demonstrates
wide
substrate
compatibility
tolerability
towards
various
functional
groups.
It
is
further
characterized
its
remarkable
efficiency
creating
chemical
bonds
achieving
high
atomic
utilization
100%.
Язык: Английский
Synthesis of 5‐Arylselenyluracils via Bromide‐Catalyzed Selective C(sp2)‐H Selenylation of Uracils
Asian Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 28, 2025
Abstract
Herein,
an
efficient
method
for
the
synthesis
of
5‐arylselenyluracils
via
bromide‐catalyzed
selective
C(
sp
2
)‐H
selenylation
uracils
using
boronic
acid
and
elemental
selenium
as
selenyl
source
was
successfully
developed.
This
proceeded
smoothly
a
series
arylboronic
acids
under
metal‐free
strong
oxidant‐free
conditions.
protocol
offered
simple
catalytic
conditions,
high
efficiency,
good
functional
group
compatibility,
easy
operation,
scalable.
Furthermore,
mechanistic
studies
suggested
that
this
transformation
possibly
undergone
radical
pathway.
Язык: Английский