Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(17), P. 3547 - 3551
Published: Jan. 1, 2023
A
highly
efficient
Rh(II)
catalyzed
non-radical
protocol
to
access
NH-free
C-3
bifunctional
oxindoles,
which
possess
3-allyl
and
3-amino
simultaneously,
was
first
achieved
by
employing
an
intermolecular
[2,3]-sigmatropic
rearrangement
reaction
between
diazooxindoles
tertiary
allylic
amines.
Utilizing
readily
available
allylamines
as
the
nitrogen
allyl
source
concurrently,
a
wide
range
of
bio-active
3-allyl-3-(amino)oxindoles
were
obtained
in
excellent
yields
under
very
mild
conditions;
meanwhile,
TON
can
be
up
90
000.
Our
study
addresses
gap
literature
investigating
rearrangements
ammonium
ylides
with
diazoamides,
have
been
relatively
understudied.
Chemistry - A European Journal,
Journal Year:
2022,
Volume and Issue:
28(71)
Published: Sept. 23, 2022
Abstract
The
gold‐catalyzed
ring‐opening
rearrangement
of
cyclopropenes
affords
an
efficient
route
to
either
polysubstituted
naphthols
or
aryl‐substituted
furans.
Owing
the
unique
dichotomy
gold−carbenes,
this
protocol
provides
a
switchable
reaction
selectivity
between
and
furans
enabled
by
use
TFP−Au(MeCN)SbF
6
(tri(2‐furyl)
phosphine)
PNP(AuNTf
2
)
(bis(diphenylphosphino)(isopropyl)
amine)
as
catalysts
respectively.
It
is
proposed
that
gold−carbene
intermediate
might
be
involved
in
cyclopropene→naphthol
while
gold‐carbocation
more
likely
cyclopropene→furan
rearrangement.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 23, 2024
A
copper-catalyzed
[2,3]-sigmatropic
rearrangement
of
azide-ynamides
via
selenium
ylides
is
disclosed,
which
leads
to
the
practical
and
divergent
synthesis
a
variety
tricyclic
heterocycles
bearing
quaternary
carbon
stereocenter
in
generally
moderate
excellent
yields.
Significantly,
this
method
represents
first
ylide
based
on
alkynes
an
unprecedented
α-imino
copper
carbenes.
New Journal of Chemistry,
Journal Year:
2021,
Volume and Issue:
46(3), P. 1018 - 1024
Published: Nov. 30, 2021
Copper-catalyzed
[4+1]
cycloannulation
of
2-aminochalcones
with
ethyl
diazophenylacetates
was
developed,
exhibiting
a
wide
range
substrates
and
good
tolerance
functional
groups.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(17), P. 3547 - 3551
Published: Jan. 1, 2023
A
highly
efficient
Rh(II)
catalyzed
non-radical
protocol
to
access
NH-free
C-3
bifunctional
oxindoles,
which
possess
3-allyl
and
3-amino
simultaneously,
was
first
achieved
by
employing
an
intermolecular
[2,3]-sigmatropic
rearrangement
reaction
between
diazooxindoles
tertiary
allylic
amines.
Utilizing
readily
available
allylamines
as
the
nitrogen
allyl
source
concurrently,
a
wide
range
of
bio-active
3-allyl-3-(amino)oxindoles
were
obtained
in
excellent
yields
under
very
mild
conditions;
meanwhile,
TON
can
be
up
90
000.
Our
study
addresses
gap
literature
investigating
rearrangements
ammonium
ylides
with
diazoamides,
have
been
relatively
understudied.
