The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14640 - 14648
Published: Sept. 29, 2023
Magnesium-mediated
reductive
carboxylation
of
p-QMs
with
CO2
via
an
Umpolung
strategy
has
been
developed,
which
can
be
used
for
the
preparation
various
aryl
acetic
acids.
This
protocol
featured
high
atom
economy,
mild
conditions,
and
operational
simplicity.
The
creation
this
will
unprecedentedly
extend
application
to
nucleophilic
reagents.
Chemistry - An Asian Journal,
Journal Year:
2023,
Volume and Issue:
19(4)
Published: Dec. 22, 2023
Abstract
We
devised
a
palladium‐catalyzed
α
‐stereoselective
glycosylation
that
incorporates
oxygen
via
in‐situ
generation
of
gem
‐disubstituted
methanols
from
p
‐quinone
methides
to
access
2,3‐unsaturated
‐diarylmethyl
O
‐glycosides
under
open‐air
atmosphere
at
room
temperature.
Advantages
this
environmentally
friendly
strategy
include
the
absence
additives
and
ligands,
using
water
as
green
source
oxygen,
mildest,
operationally
simple,
exhibiting
wide
functional
group
tolerance,
compatibility
with
variety
glycal
progenitors
in
appreciable
yields.
A
mechanistic
study
has
been
verified
H
2
18
labeling,
which
validates
(moisture)
is
sole
oxygen.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14640 - 14648
Published: Sept. 29, 2023
Magnesium-mediated
reductive
carboxylation
of
p-QMs
with
CO2
via
an
Umpolung
strategy
has
been
developed,
which
can
be
used
for
the
preparation
various
aryl
acetic
acids.
This
protocol
featured
high
atom
economy,
mild
conditions,
and
operational
simplicity.
The
creation
this
will
unprecedentedly
extend
application
to
nucleophilic
reagents.