Photoredox/Pyridine N-Oxide Catalyzed Carbohydroxylation and Aminohydroxylation of α-Olefins
Cristina Ascenzi Pettenuzzo,
Deepak Ranjan Pradhan,
Jujhar Singh
и другие.
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 15, 2025
Regioselective
carbohydroxylation
and
aminohydroxylation
of
α-olefins
were
developed
by
a
photoredox
catalyst
pyridine
N-oxide.
This
approach
offers
the
catalytic
direct
conversion
unactivated
alkenes
to
series
primary
alcohols,
including
those
bearing
β-quaternary
carbon
centers
β-amino
alcohols.
The
regioselective
difunctionalization
is
enabled
radical
addition
α-olefin
from
N-oxy
radical,
which
generated
readily
available
N-oxide
via
catalyzed
single-electron
oxidation.
A
combination
experimental
computational
mechanistic
studies
was
employed
lend
support
for
proposed
reaction
mechanism
that
proceeds
interwoven
steps
polar
substitution.
implications
this
method
further
demonstrated
examples
carboetherification,
carboesterification,
lactone
formation.
Язык: Английский
Vitamin B12 and Micellar Solution Enable Regioselective Ring Opening of Epoxides and Aziridines with Electrophilic Olefins
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 23, 2025
Vitamin
B12,
a
water-soluble
cobalt
complex,
is
inherently
predisposed
to
catalyze
reactions
under
aqueous
conditions.
Despite
its
potential,
adopting
this
strategy
for
transformations
of
hydrophobic
reagents
has
been
challenging,
because
their
low
solubility.
Here,
we
demonstrate
that
vitamin
B12
promotes
the
reaction
epoxides
and
aziridines
with
electrophilic
olefins
in
micellar
system.
The
desired
products
are
obtained
efficiently
fully
regioselective
manner.
This
green
catalytic
approach
further
advances
use
sustainable
catalysis
providing
valuable
method
synthesize
important
intermediates.
Язык: Английский
Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art
ChemPhotoChem,
Год журнала:
2024,
Номер
8(9)
Опубликована: Май 13, 2024
Abstract
The
development
of
greener
methods
for
the
preparation
three‐membered
rings
has
increased
in
last
decade,
not
only
due
to
their
biological
activity
but
also
ring
strain
those
heterocycles
that
make
them
useful
precursors
more
complex
molecules.
In
this
work,
visible‐light‐promoted
synthesis
and
ring‐opening
aziridines
epoxides,
reported
five
years,
were
reviewed.
Both
homogeneous
heterogeneous
catalysts
discussed
and,
addition,
plausible
mechanism
pathways
highlighted.
Язык: Английский
Vitamin B12 in Photocatalysis – An Underexplored Frontier in Cooperative Catalysis
ChemCatChem,
Год журнала:
2023,
Номер
16(7)
Опубликована: Дек. 23, 2023
Vitamin
B
Язык: Английский
Building Catalytic Reactions One Electron at a Time
Accounts of Chemical Research,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 24, 2024
ConspectusClassical
education
in
organic
chemistry
and
catalysis,
not
the
least
my
own,
has
centered
on
two-electron
transformations,
from
nucleophilic
attack
to
oxidative
addition.
The
focus
is
well-founded,
as
this
brand
of
enabled
incredible
feats
synthesis,
development
life-saving
pharmaceuticals
production
ubiquitous
commodity
chemicals.
With
that
said,
approach
many
ways
complementary
nature,
where
enzymes
frequently
make
use
single-electron
"radical"
steps
achieve
challenging
reactions
with
exceptional
selectivity,
including
light
detection
C-H
hydroxylation.
While
power
radical
elementary
undeniable,
fundamental
understanding
of─and
ability
apply─these
catalysis
remains
underdeveloped,
constraining
palette
which
chemists
can
new
reactions.Motivation
remedy
traditional
underemphasis
been
intensified
by
runaway
success
outer-sphere
photoredox
only
confirming
versatility
radicals
anthropogenic
but
also
teaching
value
robust
well-understood
catalytic
cycles
for
reaction
design.
Indeed,
I
would
argue
fueled
strong
its
underlying
steps,
consideration
transfer
(SET)
energetics
allowing
be
designed
Язык: Английский
Structural Evolution of Photoexcited Methylcobalamin toward a CarH-like Metastable State: Evidence from Time-Resolved X-ray Absorption and X-ray Emission
The Journal of Physical Chemistry B,
Год журнала:
2024,
Номер
128(34), С. 8131 - 8144
Опубликована: Авг. 16, 2024
CarH
is
a
protein
photoreceptor
that
uses
form
of
B
Язык: Английский