Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
43(2), P. 199 - 204
Published: Oct. 17, 2024
Comprehensive
Summary
A
tandem
Diels–Alder
reaction/Claisen
rearrangement/decarboxylation
strategy
of
N
‐allenamides
(or
aryloxyallenes)
with
3‐alkoxycarbonyl‐2‐pyrones
has
been
developed
for
the
efficient
synthesis
diarylmethanes
moderate
to
good
yields.
The
reaction
exhibits
functional
group
tolerance
and
can
be
applied
late‐stage
modifications
known
drug
molecules.
Mechanistic
studies
indicate
that
ester
at
3‐position
2‐pyrones
is
essential,
initial
between
proximal
C=C
bond
crucial
success
reaction.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(39), P. 5865 - 5868
Published: Jan. 1, 2022
A
Lewis
acid-catalyzed
[4+4]
cycloaddition
reaction
from
D–A
cyclobutanes
and
anthranils,
providing
the
corresponding
oxa-bridged
eight-membered
heterocycles
under
mild
conditions.
Chemistry - A European Journal,
Journal Year:
2021,
Volume and Issue:
27(24), P. 7154 - 7159
Published: Feb. 10, 2021
Abstract
Gold(I)‐catalyzed
higher‐order
[8+2]
cycloadditions
of
8‐aryl‐8‐azaheptafulvenes
1
with
allenamides
2
and
ynamides
3
were
studied.
1,8‐Dihydrocycloheptapyrroles
4
achieved
by
a
regioselective
cycloaddition
azaheptafulvenes
in
the
presence
(2,4‐di
t
BuC
6
H
O)
PAuNTf
as
catalyst.
Besides,
,
undergo
cycloaddition,
to
give
2‐amido‐1,4‐dihydrocycloheptapyrroles
7
JohnPhosAuNTf
Both
reactions
take
place
good
yields
variety
substituents.
A
plausible
mechanism
hypothesis
suggests
nucleophilic
attack
8‐azaheptafulvene
gold
activated
electron
rich
allene
or
alkyne
moieties
allenamide
ynamide,
respectively.
Synthesis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: June 11, 2024
Abstract
Since
their
discovery
in
2011,
gold-catalyzed
transformations
of
vinyldiazo
compounds
have
become
an
important
synthetic
tool,
enabling
the
identification
new
reaction
patterns
that
greatly
expanded
versatility
these
reagents.
In
this
short
review,
we
showcase
most
relevant
advances
been
made
exciting
area
research.
1
Introduction
2
Gold-Catalyzed
Transformations
Vinyldiazo
Compounds
Involving
Metal
Carbene
Intermediates
2.1
Liu’s
Seminal
Work:
Vinylogous
Reactivity
Au(I)
Vinyl
Carbenes
2.2
Reactions
with
Alkenes
2.3
Alkynes
2.4
Allenes
2.5
Reagents
Aromatic
2.6
Nitriles
2.7
Diazo
Cross-Couplings
3
That
Do
Not
Involve
Initial
Dinitrogen
Extrusion
3.1
Formal
[n+2]
Cycloaddition
through
Moiety
3.2
Activation
Non-Diazo
Reagent
4
Conclusions
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(26), P. 5493 - 5499
Published: June 21, 2024
A
gold-catalyzed
cycloaddition/ring
opening
of
allenamides
with
quinoline
N-oxides
has
been
developed,
which
provides
C2-alkenylated
quinolines
high
E
selectivity
in
moderate
to
yields.
It
is
noted
that
a
C8
or
C7
substituent
are
crucial
for
this
catalytic
reaction.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(28), P. 5752 - 5756
Published: Jan. 1, 2023
A
gold-catalyzed
tandem
reaction
of
o-alkynylphenols
with
diazo
compounds
has
been
developed,
providing
the
2,3-disubstituted
benzofurans
in
moderate
to
good
yields
under
mild
conditions.
In
this
protocol,
vinyl
gold
and
carbene
species
might
form
during
process.
Control
experiments
have
performed
understand
mechanism.
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(10)
Published: Aug. 21, 2023
Abstract
An
additive‐free
three‐component
reaction
of
allenamides
with
in
situ
generated
trifluoromethylnitrones
has
been
uncovered.
The
afforded
an
interesting
class
trifluoromethylated
methyleneisoxazolidines
under
mild
conditions.
Additionally,
a
gram‐scale
and
the
reductive
transformation
isoxazolidines
to
aminomethylated
allyl
alcohol
illustrate
high
synthetic
utility
present
strategy.
