Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
363(1), С. 120 - 143
Опубликована: Ноя. 14, 2020
Abstract
Recent
years
have
witnessed
a
renaissance
of
radical
cross‐coupling
cycloketone
oximes
which
served
as
active
cyanoalkyl
via
ring
fragmentation
in
various
transformations.
It
provided
an
efficient
and
practical
strategy
to
introduce
groups
into
organic
compounds
without
using
toxic
cyanide
sources.
In
this
review,
comprehensive
overview
recent
advances
the
field
redox‐active
oximes‐based
cross‐couplings
were
covered.
This
review
was
categorized
two
broad
parts:
non‐photocatalyzed
photocatalyzed
according
reaction
conditions.
Moreover,
parts
further
divided
several
sub‐sections
depending
on
nature
bond
formation.
Some
representative
examples
along
with
mechanisms
also
discussed.
magnified
image
Chemical Science,
Год журнала:
2024,
Номер
15(23), С. 8993 - 8999
Опубликована: Янв. 1, 2024
The
aromatization-driven
deconstructive
coupling
of
spiro
carbocycles
with
organic
halides
via
dual
photoredox/nickel
catalysis
is
developed.
An
in-depth
mechanism
study
revealed
that
this
reaction
proceeded
a
radical-metal
crossover
pathway.
We
describe
an
efficient
acyl
esterification
method
for
alkenes
utilizing
acyloxime
esters
as
bifunctional
reagents
featuring
radical
acylation
and
congested
C–O
bond
formation.
This
approach
is
characterized
by
mild
photoredox
conditions,
high
step
atom
economy,
a
broad
substrate
scope,
excellent
regioselectivity.
A
variety
of
valuable
α-acyl
hindered
alcohol
esters,
including
those
obtained
via
gram-scale
synthesis
late-stage
functionalization
pharmaceutical
molecules,
were
presented,
demonstrating
its
synthetic
potential
practicability.
Journal of the American Chemical Society,
Год журнала:
2020,
Номер
142(28), С. 12420 - 12429
Опубликована: Июль 2, 2020
By
utilizing
an
underexplored
reactivity
mode
of
N-aminopyridinium
ylides,
we
developed
the
visible-light-induced
ortho-selective
aminopyridylation
alkenes
via
radical-mediated
1,3-dipolar
cycloaddition.
The
photocatalyzed
single-electron
oxidation
ylides
generates
corresponding
radical
cations
that
enable
previously
inaccessible
1,3-cycloaddition
with
a
broader
range
alkene
substrates.
resulting
cycloaddition
adducts
rapidly
undergo
subsequent
homolytic
cleavage
N-N
bond,
conferring
substantial
thermodynamic
driving
force
to
yield
various
β-aminoethylpyridines.
Remarkably,
amino
and
pyridyl
groups
can
be
installed
into
both
activated
unactivated
modular
control
ortho-selectivity
1,2-syn-diastereoselectivity
under
metal-free
mild
conditions.
Combined
experimental
computational
studies
are
conducted
clarify
detailed
reaction
mechanism
origins
site
selectivity
diastereoselectivity.
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
363(1), С. 120 - 143
Опубликована: Ноя. 14, 2020
Abstract
Recent
years
have
witnessed
a
renaissance
of
radical
cross‐coupling
cycloketone
oximes
which
served
as
active
cyanoalkyl
via
ring
fragmentation
in
various
transformations.
It
provided
an
efficient
and
practical
strategy
to
introduce
groups
into
organic
compounds
without
using
toxic
cyanide
sources.
In
this
review,
comprehensive
overview
recent
advances
the
field
redox‐active
oximes‐based
cross‐couplings
were
covered.
This
review
was
categorized
two
broad
parts:
non‐photocatalyzed
photocatalyzed
according
reaction
conditions.
Moreover,
parts
further
divided
several
sub‐sections
depending
on
nature
bond
formation.
Some
representative
examples
along
with
mechanisms
also
discussed.
magnified
image
