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
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(34), P. 15480 - 15487
Published: Aug. 17, 2022
An
iridium-catalyzed
stereoselective
coupling
of
allylic
ethers
and
alkynes
to
generate
3,4-substituted
1,5-enynes
is
reported.
Under
optimized
conditions,
the
products
are
formed
with
excellent
regio-,
diastereo-,
enantioselectivities,
protocol
functional
group
tolerant.
Moreover,
we
report
conditions
that
allow
reaction
proceed
complete
reversal
diastereoselectivity.
Mechanistic
studies
consistent
an
unprecedented
dual
role
for
iridium
catalyst,
enabling
propargylic
deprotonation
alkyne
through
π-coordination,
as
well
generation
a
π-allyl
species
from
ether
starting
material.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 4, 2025
An
efficient
and
expeditious
method
to
assemble
oxa-bridged
polycycles
bearing
up
six
contiguous
stereocenters
from
a
gold(I)-catalyzed
[3
+
2]
cycloaddition/unactivated
C(sp3)-H
bond
insertion
cascade
of
o-1,6-enynyl
benzaldehydes
at
low
catalyst
loading
2
mol
%
is
described.
The Chemical Record,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 7, 2025
Abstract
Gold
catalysis
has
experienced
remarkable
progress
over
the
past
two
decades,
particularly
in
transformations
involving
alkynes.
While
numerous
aspects
of
gold‐catalyzed
reactions
have
been
extensively
reviewed,
specific
area
cascade
annulations
between
functionalized
amines
and
alkynes
represents
a
distinct
rapidly
developing
direction
that
warrants
focused
attention.
This
survey
collects
systematically
analyzes
these
transformations,
which
emerged
as
convenient
synthetic
strategies
to
diverse
nitrogen
heterocycles.
The
relevant
are
classified
firstly
by
chemical
nature
amine
functional
substituent,
secondly
size
formed
ring.
field
under
consideration
bridges
several
fundamental
practical
branches
chemistry,
including
catalysis,
organic
synthesis,
medicinal
materials
science.
Israel Journal of Chemistry,
Journal Year:
2022,
Volume and Issue:
63(9)
Published: Aug. 29, 2022
Abstract
Gold
catalysis
has
emerged
as
an
efficient
tool
for
the
selective
functionalisation
of
C−C
multiple
bonds.
Despite
significant
progress
in
this
field,
potential
asymmetric
gold
not
been
fully
explored
to
date.
A
historical
retrospect
on
area
reveals
that
enantioselective
is
based
three
pillars:
Au(I)
catalysis,
Au(III)
and
Au(I)/Au(III)
redox
catalysis.
Irrespective
mode
being
operative,
design
new
ligands
crucial
development
gold‐catalysed
organic
transformations.
This
minireview
summarizes
made
ligand
focusing
which
were
specially
designed
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(27), P. 4930 - 4934
Published: July 1, 2022
An
unprecedented
Au(I)-catalyzed
domino
intramolecular
carbonyl-alkyne
cyclization/indole
addition
strategy
has
been
disclosed
here.
This
generalized
enables
the
synthesis
of
3(2H)-furanone-incorporated
unsymmetrical
bis(indolyl)methanes
with
generation
a
stereocenter
at
furanone
junction
from
easily
accessible
indole-tethered
ynediones.
In
addition,
this
present
protocol
could
also
be
extended
for
number
indolyl-(hetero)arylmethanes
by
employing
variety
(hetero)arenes
as
nucleophile
coupling
partner.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(49)
Published: Oct. 24, 2023
Two
different
classes
of
stereoselective
cyclizations
have
been
developed
using
a
chiral
auxiliary
approach
with
commercially
available
[JohnPhosAu(MeCN)SbF6
]
as
catalyst.
First,
cascade
cyclization
1,5-enynes
was
achieved
the
Oppolzer
camphorsultam
auxiliary.
In
this
case,
one-pot
cyclization-hydrolysis
sequence
to
directly
afford
enantioenriched
spirocyclic
ketones.
Then,
alkoxycyclization
1,6-enynes
mediated
by
an
Evans-type
oxazolidinone.
A
reduction-hydrolysis
selected
remove
give
β-tetralones.
DFT
studies
confirmed
that
steric
clash
between
and
alkene
accounts
for
experimentally
observed
diastereoselective
through
Si
face.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(50), P. 27205 - 27210
Published: Dec. 8, 2023
Enantioselective
gold
catalysis
remains
a
challenging
area
of
research.
By
harnessing
gold-ligand
cooperation
in
the
presence
chiral
bifunctional
phosphine
ligand
featuring
novel
3'-phosphine
oxide
moiety,
highly
enantioselective
desymmetrization
1-ethynylcyclobutanols
is
achieved,
permitting
access
to
α-methylenecyclopentanones
diverse
array
quaternary
and
tertiary
centers.
This
cooperative
also
enables
parallel
kinetic
resolution
catalysis,
delivering
cyclopentanone
regioisomers
with
excellent
enantiomeric
excesses.
DFT
calculations
transition
states
support
distinct
mechanism
asymmetric
induction
via
controlling
conformation
bound
substrate
hence
dictating
ring
bond
undergoing
migration.
