Angewandte Chemie,
Год журнала:
2017,
Номер
130(3), С. 752 - 756
Опубликована: Ноя. 8, 2017
Abstract
A
photoinduced
cascade
strategy
leading
to
a
variety
of
differentially
functionalised
nitriles
and
ketones
has
been
developed.
These
reactions
rely
on
the
oxidative
generation
iminyl
radicals
from
simple
oximes.
Radical
transposition
by
C(sp
3
)−(sp
)
)−H
bond
cleavage
gives
access
distal
carbon
that
undergo
S
H
2
functionalisations.
mild,
visible‐light‐mediated
procedures
can
be
used
for
remote
fluorination,
chlorination,
azidation,
were
applied
modification
bioactive
structurally
complex
molecules.
Chemical Science,
Год журнала:
2018,
Номер
9(27), С. 5883 - 5889
Опубликована: Янв. 1, 2018
Fine-tuned
organic
photoredox
catalysts
are
introduced
for
the
metal-free
alkynylation
of
alkylnitrile
radicals
generated
via
oxidative
ring
opening
cyclic
alkylketone
oxime
ethers.
Organic Letters,
Год журнала:
2017,
Номер
19(21), С. 5908 - 5911
Опубликована: Окт. 26, 2017
A
direct
C–H
cyanoalkylation
of
heteroaromatic
N-oxides
and
quinones
with
cyclobutanone
oximes
is
reported.
This
redox-neutral,
operationally
simple
reaction
successfully
amenable
to
a
wide
range
N-oxides,
quinones,
oximes.
novel
catalytic
system
consisting
nickel
source
proved
crucial
for
cleavage
the
C–C
bond
selective
formation
over
β-hydride
elimination.
Mechanistic
studies
suggest
that
radical
intermediate
might
be
involved
in
this
transformation.
Organic Letters,
Год журнала:
2018,
Номер
20(17), С. 5523 - 5527
Опубликована: Авг. 23, 2018
A
unified
strategy
for
intermolecular
remote
C(sp3)–H
and
C–C
vinylation
of
O-acyl
oximes
with
vinyl
boronic
acids
has
been
achieved.
This
is
enabled
by
photoreductive
generation
iminyl
radicals
from
under
irradiation
visible
light.
The
translocated
carbon-centered
radicals,
which
are
generated
the
through
1,5-hydrogen
atom
transfer
or
cleavage,
can
be
vinylated
acids.
opens
up
a
new
approach
to
functionalization
via
cleavage
provides
an
efficient
versatile
solution
synthesis
γ-vinylation
ketones
nitriles.
Chemical Science,
Год журнала:
2018,
Номер
10(1), С. 161 - 166
Опубликована: Окт. 2, 2018
An
efficient
transition-metal
free
C–C
bond
cleavage/borylation
of
cycloketone
oxime
esters
has
been
described.
In
this
reaction,
the
B2(OH)4
reagent
not
only
served
as
boron
source
but
also
acted
an
electron
donor
through
formation
a
complex
with
DMAc-like
Lewis
base.
ACS Catalysis,
Год журнала:
2019,
Номер
9(9), С. 8159 - 8164
Опубликована: Авг. 1, 2019
A
visible
light-induced
and
exogenous
photosensitizer-free,
copper-catalyzed
radical
aminocarbonylation
of
cycloketone
oxime
esters
with
CO
gas
amines
is
developed.
The
mild
catalytic
system
involving
CuCl
N,N,N-tridentate
ligand
shows
good
reactivity
chemoselectivity,
tolerates
a
wide
range
alkyl/aryl
amines,
giving
the
corresponding
cyanoalkylated
amides
in
moderate
to
yields.
Preliminary
mechanistic
studies
suggest
that
reaction
involves
CuI/CuII/CuIII-based
cycle
intermediate.
Organic Letters,
Год журнала:
2019,
Номер
21(10), С. 3769 - 3773
Опубликована: Май 7, 2019
A
visible-light-promoted
redox
neutral
γ,γ-difluoroallylation
of
cycloketone
oxime
ethers
with
trifluoromethyl
alkenes
through
C–C
and
C–F
bond
cleavage
has
been
achieved,
which
affords
various
cyano-substituted
gem-difluoroalkenes
in
generally
good
yields.
The
reaction
provides
a
facile
protocol
for
forming
gem-difluoroalkene
functionality
cyano
group
while
incorporating
them
into
one
molecule.
conversion
the
resulting
to
cyclic
monofluoroalkenes
via
second
was
also
described.
ACS Catalysis,
Год журнала:
2017,
Номер
7(12), С. 8441 - 8445
Опубликована: Ноя. 8, 2017
A
nickel-catalyzed
1,2-aminoarylation
of
oxime-ester-tethered
alkenes
with
boronic
acids
was
developed.
variety
pyrroline
derivatives
were
synthesized
in
good
yields
via
the
successive
formation
C(sp3)–N
and
C(sp3)–C(sp2)
bonds.
For
cyclobutanone-derived
oxime
esters,
reaction
provided
aliphatic
nitriles
incorporating
an
aromatic
group
γ-position.
mechanism
involving
iminyl
radical
carbon-centered
intermediates
proposed.
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.
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