The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(21), С. 14596 - 14608
Опубликована: Окт. 3, 2022
The
scope
of
an
umpolung
approach
to
expand
synthetic
access
bifunctional
γ-keto
hydrazine
intermediates
via
electrophilic
amination
β-homoenolates
derived
from
cyclopropanol
precursors
that
took
advantage
azodicarboxylates
or
azodicarboxamides
as
electron-deficient
nitrogen
sources
was
examined.
This
new
procedure
avails
commercially
available
readily
accessible
starting
materials
along
with
a
ligand-free
Cu(II)
salt
inexpensive
catalyst.
Using
this
operationally
simple
reaction,
which
proceeds
under
mild
conditions
(open-flask
and
ambient
temperature)
is
suitable
for
multigram
scale,
preparative
applications
were
established
range
aryl-
alkyl-substituted
cyclopropanols
azodicarboxylate/azodicarboxamide
substrates
(26
examples,
74-95%
yields).
Further,
the
obtained
products
have
been
shown
provide
convenient
γ-hydroxy
hydrazide,
γ-amino
heterocyclic
derivatives.
Organic Letters,
Год журнала:
2022,
Номер
24(14), С. 2699 - 2704
Опубликована: Апрель 7, 2022
Herein,
we
reported
a
Ni-catalyzed
carbonylation
of
cyclopropanol
with
benzyl
bromide
to
afford
multisubstituted
cyclopentenone
under
1
atm
CO.
The
reaction
proceeds
through
cascade
bromides,
followed
by
generation
nickel
homoenolate
from
cyclopropanols
via
β-C
elimination
1,4-diketones,
which
undergoes
intramolecular
Aldol
condensation
furnish
highly
substituted
derivatives
in
moderate
good
yields.
exhibits
high
functional
group
tolerance
broad
substrate
scope.
Organic Letters,
Год журнала:
2024,
Номер
26(9), С. 1834 - 1839
Опубликована: Фев. 22, 2024
Efficient
access
to
multiple
functionalized
allenes
via
a
three
component
1,4-alkylcyanation
of
enynes
with
cyclic
alcohol
derivatives
in
the
presence
trimethylsilyl
cyanide
(TMSCN)
under
copper/photoredox
dual
catalysis
has
been
developed.
Both
easily
transformable
aldehyde
and
cyano
groups
were
introduced
tetra-substituted
through
light-induced
C–C
bond
cleavage
butanol
pentanol
derivatives.
The
reactions
proceeded
smoothly
mild
conditions
broad
functional
tolerance.
Journal of the American Chemical Society,
Год журнала:
2022,
Номер
144(20), С. 9161 - 9171
Опубликована: Май 12, 2022
Herein,
we
report
a
photoinduced
transition-metal-free
C(aryl)-N
bond
formation
between
2,4,6-tri(aryl)boroxines
or
arylboronic
acids
as
an
aryl
source
and
1,4,2-dioxazol-5-ones
(dioxazolones)
amide
coupling
partner.
Chloride
anion,
either
generated
Green Chemistry,
Год журнала:
2024,
Номер
26(3), С. 1375 - 1380
Опубликована: Янв. 1, 2024
A
visible-light-mediated
tandem
ring
opening/1,6-conjugate
addition
of
cyclobutanols
with
p
-quinone
methides
was
developed.
This
protocol
allowed
the
formation
δ,δ-diaryl
ketones
in
presence
a
readily
available
organic
photocatalyst.
Organic Letters,
Год журнала:
2022,
Номер
24(32), С. 6000 - 6005
Опубликована: Авг. 10, 2022
A
Rh-catalyzed
weak
chelation-guided
C4-alkylation
of
indoles
has
been
accomplished
using
cyclopropanols
as
an
alkylating
agent
via
the
cascade
C–H
and
C–C
bond
activation.
The
substrate
scope,
functional
group
tolerance,
late-stage
mutation
drug
molecules
are
important
practical
features.
ACS Catalysis,
Год журнала:
2023,
Номер
13(7), С. 4362 - 4368
Опубликована: Март 15, 2023
The
transition-metal-catalyzed
intramolecular
hydroarylation
of
alkenes
has
been
recognized
as
a
straightforward
approach
for
the
construction
3,3-disubstituted
2,3-dihydrobenzofurans.
reactions
mainly
rely
on
reductive
Heck
reaction
aryl
halides
or
direct
C–H
bond
activation
arenes
bearing
directing
group.
This
work
realizes
Rh-catalyzed
olefin-tethered
benzocyclobutenols
via
C–C
activation,
which
offers
an
alternative
to
2,3-dihydrobenzofurans
4-β-keto
moiety.
methodology
features
100%
atom
economy
and
pH-
redox-neutral
conditions,
is
applicable
late-stage
functionalization
complex
molecules.
asymmetric
variant
also
achieved
with
excellent
enantioselectivities.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(7), С. 1559 - 1564
Опубликована: Фев. 14, 2024
Abstract
A
photoredox/copper
co‐catalyzed
ring‐opening
cross‐coupling
of
aryl
azides
with
cyclopropanols
has
been
developed
fac
‐Ir(ppy)
3
as
the
photocatalyst.
The
reaction
involves
intermediacy
anilino
radical
generated
through
reduction
azido
group
by
*
and
[Cu
II
]‐enabled
oxidative
cyclopropanol.
An
array
β‐aminoketone
compounds
were
synthesized
under
redox‐neutral
conditions
using
this
method.
ACS Catalysis,
Год журнала:
2022,
Номер
12(15), С. 9690 - 9697
Опубликована: Июль 26, 2022
We
herein
report
a
modular
strategy,
which
enables
Rh(III)-catalyzed
diastereoselective
3,4-amino
oxygenation
and
diamination
of
1,3-dienes
using
different
O-
N-nucleophiles
in
combination
with
readily
available
3-substituted
1,4,2-dioxazolones
(78
examples,
37–91%
yield).
Previous
attempts
to
functionalize
the
internal
double
bond
rested
on
use
plain
alcoholic
solvents
as
nucleophilic
coupling
partners
thus
dramatically
limiting
scope
this
transformation.
have
now
identified
hexafluoroisopropanol
non-nucleophilic
solvent
that
allows
diverse
nucleophiles
greatly
expands
scope,
including
an
unprecedented
amino
hydroxylation
selectively
install
valuable,
unprotected
β-amino
alcohols
across
1,3-dienes.
Moreover,
various
elaborate
prove
be
compatible
providing
unique
access
complex
organic
molecules.
Finally,
method
is
employed
series
intramolecular
reactions
deliver
valuable
nitrogen
heterocycles
well
γ-
δ-lactones.
Organic Letters,
Год журнала:
2023,
Номер
25(11), С. 1845 - 1849
Опубликована: Март 10, 2023
A
rhodium(III)-catalyzed
protocol
for
the
synthesis
of
pyrrolo[1,2-a]quinolines
through
intramolecular
annulation
o-alkynyl
amino
aromatic
ketones
and
subsequent
aromatization
is
reported.
This
transformation
builds
pyrrole
quinoline
moieties
pyrrolo[1,2-a]quinoline
in
one
pot
achieves
a
flexible
introduction
different
substituent
groups
at
4-
5-positions
on
products
that
were
difficult
to
prepare
by
other
means.
The
reaction
proceeds
smoothly
gram
scale,
are
amenable
downstream
synthetic
manipulations.
