HFIP-Mediated, Regio-, and Stereoselective Hydrosulfenylation of Ynamides: A Versatile Strategy to Access Ketene N,S-Acetals
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Herein,
we
report
an
HFIP-mediated,
versatile,
sustainable,
atom-economical,
and
regio-
stereoselective
hydro-functionalization
of
ynamides
with
various
S-nucleophiles
(1
equiv.)
such
as
thiols,
thiocarboxylic
acids,
carbamates,
xanthates,
O,O-diethyl
S-hydrogen
phosphorothioate
to
access
a
wide
variety
stereodefined
trisubstituted
ketene
N,S-acetals
under
mild
conditions.
This
protocol
requires
only
HFIP,
which
plays
multiple
roles,
acting
Brønsted
acid
protonate
the
ynamide
regioselectively
at
beta
carbon
generate
reactive
keteniminium
intermediate,
stabilizing
intermediate
solvent
through
H-bonding.
After
nucleophilic
attack
S-nucleophile
on
deprotonation,
HFIP
is
regenerated
in
most
cases
can
be
easily
recovered
recycled,
revealing
high
sustainability
protocol.
Remarkably,
all
reactions
are
highly
efficient
furnish
excellent
yields
many
pure
products
were
obtained
just
by
washing
crude
reaction
mixture
pentane.
Significantly,
green
chemistry
metrics
found
excellent.
Язык: Английский
Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 12, 2025
Organoselenium
compounds
and
quinolines
are
widely
used
in
drugs
materials.
Herein,
we
report
an
electro-oxidative
cyclization
between
isocyanides
diselenides
to
effectively
synthesize
2-organoselenyl
a
simple
undivided
cell
without
transition-metal
catalysts
or
toxic
oxidants.
Gram-scale
synthesis
postsynthetic
modifications
highlighted
the
practicality
of
this
electrochemical
strategy.
A
series
produced
with
up
82%
yield,
good
functional
group
tolerance
high
atom
efficiency
under
room
temperature.
Язык: Английский
Electrochemically Chalcogenative Annulation Enabled Construction of Functionalized Saturated N-Heterocycles†
Chemical Communications,
Год журнала:
2024,
Номер
60(74), С. 10156 - 10159
Опубликована: Янв. 1, 2024
An
efficient
chalcogenative
annulation
strategy
for
constructing
functionalized
saturated
N-heterocycles
from
unactivated
alkenes
with
dichalcogenides
under
electrochemical
conditions
has
been
presented.
This
protocol
is
applicable
to
mono-,
di-
or
tri-substituted
alkenes,
providing
a
straightforward
pathway
aziridines,
azetidines,
pyrrolidines,
and
piperidines
high
regioselectivity.
Moreover,
the
qualified
realize
oxychalcogenation
of
as
well.
Язык: Английский
Electrochemically promoted selenocyclization for the synthesis of organoselenyl isoxazoles
Green Chemistry,
Год журнала:
2024,
Номер
26(19), С. 10240 - 10246
Опубликована: Янв. 1, 2024
Herein,
we
report
a
general
and
sustainable
electrochemically
promoted
oxidative
selenocyclization
protocol
for
the
synthesis
of
organoselenyl
isoxazoles
from
2-alkyn-1-one
O
-methyloximes
diorganyl
diselenides.
Язык: Английский
Visible-Light-Mediated, Organophotocatalytic C–H Thiocyanation of Pyrazolo[1,5-a]pyrimidines
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(18), С. 13215 - 13223
Опубликована: Сен. 11, 2024
Herein,
we
report
a
metal-free,
organophotoredox-catalyzed
sustainable
C-H
thiocyanation
of
biologically
active
class
N-heterocycles,
pyrazolo[1,5-
Язык: Английский