Photocatalyzed Carbon─Carbon Bond Formation Between Ethylene Glycol and Electron‐Deficient Olefins
ChemistrySelect,
Год журнала:
2025,
Номер
10(1)
Опубликована: Янв. 1, 2025
Abstract
Ethylene
glycol
is
produced
on
a
very
large
industrial
scale
and
used
for
the
preparation
of
polyesters
antifreeze
formulations.
Although
diol
mainly
manufactured
from
fossil‐based
resources,
new
commercial
procedures
carbohydrates
are
currently
being
introduced,
which
eventually
will
make
ethylene
an
important
bio‐derived
compound
in
organic
chemistry.
However,
further
transformations
formation
carbon─carbon
bonds
have
so
far
received
relatively
little
attention.
In
present
work,
photocatalyzed
coupling
between
electron‐deficient
olefins
therefore
investigated.
The
results
show
that
iridium
complex
can
be
employed
to
mediate
reaction
with
acrylates,
acrylamides,
acrylonitriles,
vinyl
sulfones
generate
range
chain‐elongated
lactones
diols.
Substituents
tolerated
α
position
acrylates
while
poor
outcome
obtained
substituents
β
olefin.
illustrate
abundant
alcohol
by
use
photocatalytic
transformations.
Язык: Английский
Reactivity of Alcohol Substrates and Boron-Containing Complexes in C–H Alkylation Enabled by Photoredox, Hydrogen Atom Transfer, and Boronic Acid Catalysis
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 21, 2025
Using
boronic
acid,
photoredox,
and
HAT
catalysis,
the
relative
alkylation
reactivity
of
representative
alkyl
alcohols
was
evaluated
through
competition
experiments,
revealing
higher
initial
for
diols.
Electron-poor
arylboronic
acid
catalysts
provide
increased
reaction
efficiency
all
substrates,
which
is
attributed
to
a
more
dynamic
facile
equilibrium
between
boron-containing
species.
Furthermore,
β-carboxyboronic
acids
resulted
in
an
additional
increase
efficiency,
results
from
both
catalyst
classes
were
compared
using
kinetic
profiles
select
scope
monoalcohols.
Язык: Английский
Photoredox/Nickel Dual-Catalyzed Allylation of Aldehydes with Allylic Alcohols and Mechanistic Insights in the Presence of CO2
ACS Catalysis,
Год журнала:
2024,
Номер
14(16), С. 12392 - 12402
Опубликована: Авг. 5, 2024
Direct
utilization
of
allylic
alcohols
as
reagents
without
metal
reductants
has
drawn
significant
attention.
Herein,
we
report
a
practical,
diastereoselective
photoredox/Ni(II)-dual-catalyzed
reductive
allylation
reaction
aldehydes
with
readily
accessible
in
the
presence
CO2.
This
methodology
allows
branched
regioselective
direct
wide
range
various
good
to
high
yield
and
up
>20:1
d.r.
ratio.
Accurate
DFT
calculations
revealed
rationale
behind
diastereoselectivity
differences
via
Zimmerman–Traxler
transition
state
for
different
substrates,
while
also
delineated
energetically
most
favorable
mechanistic
pathway
this
reaction.
Язык: Английский
Low‐Impact Synthesis of γ‐Lactones through Photoinduced Baeyer‐Villiger Oxidation of Cyclic Ketones
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(21)
Опубликована: Апрель 5, 2024
Abstract
A
photocatalyzed
oxidation
of
functionalized
cyclobutanones
to
access
γ‐lactones
has
been
performed
in
acetonitrile
at
room
temperature,
using
anthraquinone
derivatives
as
catalysts
the
presence
TFA.
The
best
reaction
results
were
obtained
by
3
mol
%
9,10‐anthraquinone
a
catalyst
under
370
nm
irradiation
an
O
2
environment.
scope
and
limitations
this
have
investigated
both
2‐
3‐substituted
cyclobutanones,
well
enantiopure
ketones,
obtain
full
preservation
their
stereochemical
identity
after
oxidation.
process
furnishes
most
cases
desired
compounds
with
high
purity
removal
simple
filtration,
reducing
production
solvents
waste.
Язык: Английский