Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(35), P. 6571 - 6576
Published: Aug. 30, 2023
A
practical
and
precise
method
for
visible-light-promoted
deoxygenative
deuteration
of
common
aliphatic
alcohols
using
D2O
as
the
deuterium
source
is
reported.
Upon
intermediacy
xanthate
anions,
a
variety
primary,
secondary,
tertiary
can
be
facilely
transformed
into
deuterioalkanes
with
excellent
D-incorporation
at
predicted
sites.
The
deoxygenation
sequence
catalyzed
by
in
situ
formed
deuterated
2-mercaptopyridine,
which
plays
dual
roles
atom
transfer
catalyst
an
electron
shuttle
well.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(9), P. 6334 - 6344
Published: April 15, 2024
A
one-pot
strategy
for
deoxygenative
alkylation
of
alcohols
with
quinoxalin-2(1H)-ones
was
developed
by
using
xanthate
salts
as
alcohol-activating
groups
radical
generation
in
the
presence
tricyclohexylphosphine
under
visible-light-promoted
conditions.
The
remarkable
features
this
reaction
include
a
broad
substrate
scope,
excellent
functional
group
tolerance,
mild
conditions,
and
simple
operation.
Moreover,
synthetic
utility
validated
success
two-step
reactions,
scale-up
synthesis,
chemoselective
monodeoxygenation
diols.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(22), P. 4070 - 4074
Published: June 1, 2022
Reactions
involving
an
alkyl
radical
generated
from
a
primary
alcohol
by
photochemistry
are
rare
and
challenging.
Herein,
we
present
photocatalyst-
metal-free
approach
that
enables
the
generation
of
corresponding
subsequent
C(sp3)-C(sp3)
bond
formation
with
activated
olefin,
via
thianthrenium
salt/Hantzsch
ester
electron
donor-acceptor
complex.
This
protocol
for
conversion
C-OH
to
C-C
is
highly
functionality
tolerant
can
successfully
be
used
in
late-stage
functionalization
pharmaceuticals.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(35), P. 6571 - 6576
Published: Aug. 30, 2023
A
practical
and
precise
method
for
visible-light-promoted
deoxygenative
deuteration
of
common
aliphatic
alcohols
using
D2O
as
the
deuterium
source
is
reported.
Upon
intermediacy
xanthate
anions,
a
variety
primary,
secondary,
tertiary
can
be
facilely
transformed
into
deuterioalkanes
with
excellent
D-incorporation
at
predicted
sites.
The
deoxygenation
sequence
catalyzed
by
in
situ
formed
deuterated
2-mercaptopyridine,
which
plays
dual
roles
atom
transfer
catalyst
an
electron
shuttle
well.
