The Journal of Organic Chemistry,
Journal Year:
2018,
Volume and Issue:
83(24), P. 15438 - 15448
Published: Nov. 30, 2018
A
copper-catalyzed
iminyl
radical-mediated
C–C
bond
cleavage/cross-coupling
tandem
reaction
of
cyclobutanone
oxime
esters
with
aryl
thiols
in
the
presence
1,8-diazabicyclo[5.4.0]undec-7-ene
(DBU)
at
room
temperature
was
developed,
and
cyanopropyl
sulfides
were
smoothly
synthesized
20–88%
yields.
By
altering
copper
reagent
molar
ratio
ester/aryl
thiol/DBU,
substitutional
product
N-arylthio
imines
selectively
generated
50–91%
Using
this
protocol,
C–S
N–S
formations
using
as
sulfur
sources
realized
under
very
mild
conditions
without
use
photocatalysis
electrocatalysis
techniques.
ACS Catalysis,
Journal Year:
2019,
Volume and Issue:
9(5), P. 4179 - 4188
Published: March 28, 2019
A
4-HO-TEMPO-catalyzed
redox
strategy
for
the
synthesis
of
pyridines
through
annulation
cyclopropanols
and
oxime
acetates
has
been
developed.
This
protocol
features
good
functional
group
tolerance
high
chemoselectivity
also
promises
to
be
efficient
late-stage
functionalization
skeletons
drugs
natural
products.
Mechanism
studies
indicate
that
reaction
involves
in
situ
generated
α,β-unsaturated
ketones
imines
as
key
intermediates,
which
are
derived
from
via
a
TEMPO/TEMPOH
cycle,
respectively.
The
pyridine
products
formed
result
enones
with
followed
by
TEMPO-catalyzed
oxidative
aromatization
excess
acetates.
method
not
only
realizes
but
broadens
frontiers
TEMPO
catalysis.
Organic Chemistry Frontiers,
Journal Year:
2019,
Volume and Issue:
6(8), P. 1146 - 1150
Published: Jan. 1, 2019
A
cooperative
base
system
has
been
developed
for
the
novel
three-component
synthesis
of
2-aminobenzo[4,5]thieno[3,2-d]thiazoles
via
bis-heterocyclization
methylketoxime
acetates.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(21), P. 8630 - 8634
Published: Oct. 16, 2019
A
three-component
cascade
bis-heteroannulation
reaction
is
described
that
provides
access
to
a
variety
of
benzo[4,5]thieno[3,2-c]isoquinoline
and
thieno[3,2-c]isoquinoline
compounds
from
easily
available
methylketoximes,
o-halobenzaldehydes,
elemental
sulfur.
Mechanistic
studies
reveal
two-step
process
involving
sequential
copper
sulfur
catalysis
relay.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(37), P. 7391 - 7404
Published: Jan. 1, 2022
This
review
mainly
focuses
on
the
recent
advances
in
Co-catalyzed
[2
+
2
2]
cycloaddition
reaction
of
alkynes
with
nitriles
to
access
multi-substituted
pyridines.
Meanwhile,
brief
mechanistic
insights
are
also
discussed
explain
observed
regioselectivity.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(21), P. 8533 - 8536
Published: Oct. 11, 2019
A
copper-catalyzed
oxidative
cyclization
of
oxime,
arylthiol,
and
trifluoroacetic
anhydride
for
the
construction
trisubstituted
oxazoles
has
been
developed.
This
transformation
combines
N–O
bond
cleavage,
C–H
functionalization,
intramolecular
annulation,
providing
a
practical
protocol
introduction
trifluoromethyl
(−CF3)
group
at
oxazole
rings.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(3), P. 936 - 942
Published: Jan. 14, 2021
A
copper-based
catalytic
system
has
been
developed
to
enable
efficient
cyclization
of
ketoxime
acetates
with
o-fluorobenzaldehydes.
This
protocol
offers
an
method
for
the
synthesis
substituted
quinoline
derivatives
a
broad
range
compatible
functionalities.
The
present
also
provides
rapid
access
synthetically
and
pharmaceutically
useful
quinoline-fused
polycycles
such
as
benzo[c]acridines.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(20), P. 8239 - 8243
Published: Oct. 3, 2019
A
novel
copper-catalyzed
oxidative
formal
[3
+
2]
annulations
of
ketoxime
acetates
and
tetrohydroisoquinolines
for
the
synthesis
fused
pyrazoles
imidazoles
has
been
developed.
broad
range
important
isoquinoline-fused
pyrazole
imidazole
products
were
selectively
generated
by
key
control
oxidant.
Organic & Biomolecular Chemistry,
Journal Year:
2017,
Volume and Issue:
16(1), P. 124 - 129
Published: Nov. 27, 2017
Pyridine
formation
with
oxime
acetates
as
the
building
blocks
under
metal-free
conditions
is
described.
Ammonium
iodide
has
proved
to
be
a
highly
efficient
promoter
for
N-O
bond
reduction
and
subsequent
condensation
reactions,
whereby
it
played
dual-function
role
in
transformation.
While
three-component
reaction
of
acetates,
benzaldehydes,
1,3-dicarbonyls
proceeded
well
assistance
stoichiometric
amount
ammonium
iodide,
oximes
acroleins
was
enabled
by
using
catalytic
initiator
afford
substituted
pyridines.
By
this
protocol,
pyridine
products
were
generated
moderate
excellent
yields
tolerance
towards
broad
range
functional
groups.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(15), P. 6117 - 6121
Published: July 20, 2020
A
copper(0)/PPh3-mediated
cascade
bisheteroannulation
reaction
of
o-nitroalkynes
with
methylketoximes
has
been
developed
that
provides
viable
access
to
a
diverse
range
pyrazo-fused
pseudoindoxyl
compounds.
Synthetically
useful
functional
groups
including
sensitive
C-I
bonds
are
compatible
this
system.
Mechanistic
studies
suggest
involving
sequential
PPh3-mediated
deoxygenative
cycloisomerization
and
copper-catalyzed
[3
+
2]
pyrazo-annulation.
