Visible Light-Mediated Aza-Norrish–Yang Type Cyclization
ACS Catalysis,
Год журнала:
2025,
Номер
unknown, С. 6473 - 6485
Опубликована: Апрель 6, 2025
Язык: Английский
Microfluidic Photocatalytic Ring Expansion of Sulfonium Salts for the Synthesis of Cyclic Sulfides
ACS Catalysis,
Год журнала:
2025,
Номер
unknown, С. 6507 - 6513
Опубликована: Апрель 6, 2025
Cyclic
sulfides
are
relevant
building
blocks
in
medicinal
and
synthetic
chemistry,
with
applications
ranging
from
drug
discovery
to
materials
science.
However,
the
synthesis
of
medium-sized
cyclic
(6-8-membered
rings)
remains
largely
underdeveloped.
Herein,
we
report
a
photocatalytic
ring-expansion
strategy
for
sulfonium
salts,
granting
access
six-,
seven-,
eight-membered
very
high
regio-
diastereocontrol.
The
implementation
method
under
continuous
flow
was
key
increasing
efficiency
minimizing
product
decomposition.
Mechanistic
investigations
revealed
formation
benzylic
radicals
carbocation
intermediates
that
control
diastereoselectivity
observed.
Finally,
utility
this
approach
demonstrated
sulfoxides
sulfones,
which
can
be
easily
obtained
corresponding
sulfide
products.
Язык: Английский
Access to Methylidene-Azaspiro[4.5]decatrienones via Radical-Promoted Domino Thio-Functionalization/Dearomative Ipso-Annulation
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 9, 2025
An
unprecedented
approach
involving
radical-mediated
sulfonylation/dearomative
ipso-annulation
of
N-(methyl-2-phenylacetate)propiolamides
using
arylsulfonyl
radical,
generated
from
aryl
diazonium
salt
in
the
presence
DABSO,
is
developed.
This
strategy
provides
uniquely
substituted
3-sulfonyl
azaspiro[4.5]decatrienones
good
yields.
The
developed
has
also
been
extended
fruitfully
to
3-thiocyano
aza-spirocycles
through
domino
thiocyanation/dearomative
ipso-annulation.
Язык: Английский