The Journal of Organic Chemistry,
Год журнала:
2018,
Номер
83(24), С. 15438 - 15448
Опубликована: Ноя. 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.
Green Chemistry,
Год журнала:
2019,
Номер
21(6), С. 1505 - 1516
Опубликована: Янв. 1, 2019
A
procedure
was
developed
for
the
synthesis
of
fluorinated
2-aminopyridines
based
on
reactions
1,1-enediamines,
benzaldehydes
and
1,3-dicarbonyl
compounds.
Organic Letters,
Год журнала:
2020,
Номер
22(24), С. 9658 - 9664
Опубликована: Ноя. 25, 2020
A
visible-light
photoredox-catalyzed
formal
[5
+
1]
cycloaddition
of
N-tosyl
vinylaziridines
with
difluoroalkyl
halides
as
unique
C1
synthons
was
developed.
The
procedure
provides
an
efficient
and
practical
method
to
synthesize
diverse
pyridines
in
moderate
good
yields.
reaction
underwent
a
radical-initiated
kinetically
controlled
ring-opening
involved
key
α,β-unsaturated
imine
intermediate,
followed
by
E2
elimination,
6π
electrocyclization,
defluorinated
aromatization.
Organic Letters,
Год журнала:
2020,
Номер
22(9), С. 3381 - 3385
Опубликована: Апрель 13, 2020
A
copper-catalyzed
annulation
of
oxime
acetates
and
α-amino
acid
ester
derivatives
for
the
easy
preparation
4-pyrrolin-2-ones
bearing
a
3-amino
group
has
been
developed.
This
process
features
oxidation
amines
with
esters
as
internal
oxidant
to
produce
active
1,3-dinucleophilic
1,2-dielectrophilic
species
concurrently.
The
subsequent
nucleophilic
cyclization
realizes
efficient
construction
4-pyrrolin-2-one
derivatives.
The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
85(12), С. 8157 - 8165
Опубликована: Июнь 1, 2020
The
NH4I-triggered
formal
[4
+
2]
annulation
of
α,β-unsaturated
ketoxime
acetates
with
N-acetyl
enamides
has
been
developed.
current
protocol
employs
electron-rich
as
C2
synthons
and
enables
the
efficient
straightforward
construction
polysubstituted
pyridines
in
moderate
to
good
yields
based
on
metal-free
systems.
reaction
tolerates
a
wide
range
functional
groups
represents
an
alternate
route
toward
synthesis
pyridine
derivatives.
Green Synthesis and Catalysis,
Год журнала:
2021,
Номер
2(2), С. 237 - 240
Опубликована: Март 28, 2021
The
iron-catalyzed
[4
+
2]
annulation
of
α,β-unsaturated
ketoxime
acetates
with
enaminones
has
been
developed,
providing
efficient
access
to
highly
substituted
pyridines
in
moderate
good
yields.
Notable
features
the
present
strategy
include
low-cost
catalytic
system,
simple
and
mild
reaction
condition
wide
substrate
scope.
Mechanistic
studies
reveal
that
FeCl2
may
directly
serve
as
a
Lewis
acid
activate
for
nucleophilic
addition.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(9)
Опубликована: Янв. 2, 2023
Abstract
This
review
provides
a
comprehensive
overview
of
strategies
and
methodologies
for
reducing
C−O
heteroatomic−oxygen
bonds
(N−O,
S−O,
P−O)
using
I
2
/I
−
,
as
well
other
synthetically
relevant
such
C−C,
N−N,
C−N,
C−X,
C−S.
It
highlights
discusses
most
the
mechanistic
details
provided
by
original
authors.
Selected
examples
halides
(Br
Cl)
reductants
are
also
covered.
Organic Letters,
Год журнала:
2023,
Номер
25(51), С. 9237 - 9242
Опубликована: Дек. 14, 2023
With
cyanopyridines
and
alkyl
bromides
as
coupling
partners,
an
electrochemically
driven
C4-selective
decyanoalkylation
has
been
established
to
access
diverse
4-alkylpyridines
in
one
step.
The
reaction
proceeds
through
the
single
electron
reduction/radical–radical
tandem
process
under
mild
electrolytic
conditions,
achieving
cleavage
of
C(sp2)–CN
bond
formation
C(sp3)–C(sp2).
practicality
this
protocol
is
illustrated
by
no
sacrificial
anodes,
a
broad
substrate
scope,
gram-scale
synthesis.
European Journal of Organic Chemistry,
Год журнала:
2018,
Номер
2018(23), С. 2963 - 2971
Опубликована: Апрель 21, 2018
A
mild
domino
rearrangement
strategy
for
the
direct
access
to
substituted
quinoline‐4‐carboxamides
has
been
developed.
This
copper‐catalyzed
coupling
reaction
of
O
‐acyl
oximes
with
isatins
in
presence
molecular
oxygen
as
sole
oxidizing
agent
proceeds
through
a
ring
expansion
cleavage
two
C–N
bonds.
Organic & Biomolecular Chemistry,
Год журнала:
2017,
Номер
15(47), С. 10024 - 10028
Опубликована: Янв. 1, 2017
2-Substituted-benzothiazole
derivatives
were
selectively
prepared
from
2-aminothiophenols
and
arylacetylenes
or
styrenes
using
elemental
sulfur
as
the
efficient
oxidant.
Chinese Journal of Chemistry,
Год журнала:
2021,
Номер
39(5), С. 1175 - 1180
Опубликована: Янв. 23, 2021
Main
observation
and
conclusion
A
facile
copper‐based
catalytic
system
has
been
developed
to
enable
efficient
cyclization
of
methylketoximes
alkynals.
This
protocol
provides
a
viable
entry
synthetically
pharmaceutically
useful
2‐acylpyrroles
with
broad
range
compatible
functionalities.
Mechanistically,
key
acyl
migration
is
probably
involved
that
leads
the
formation
N
‐acyl
pyrroles
or
otherwise
NH
by
further
hydrolysis.
More
importantly,
present
reaction
also
gives
an
opportunity
realize
three‐component
pyrrole
assembly
simple
addition
carboxylic
acid.
