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(16), P. 7089 - 7095
Published: April 18, 2022
Presented
herein
is
the
first
report
of
enantioselective
Au(I)/Au(III)
redox
catalysis,
enabled
by
a
newly
designed
hemilabile
chiral
(P,N)-ligand
(ChetPhos).
The
potential
this
concept
has
been
demonstrated
development
1,2-oxyarylation
and
1,2-aminoarylation
alkenes
which
provided
direct
access
to
medicinally
relevant
3-oxy-
3-aminochromans
(up
88%
yield
99%
ee).
DFT
studies
were
carried
out
unravel
enantiodetermining
step,
revealed
that
stronger
trans
influence
phosphorus
allows
selective
positioning
substrate
in
C2-symmetric
environment
present
around
nitrogen,
imparting
high
level
enantioselectivity.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(9), P. 2359 - 2384
Published: Jan. 1, 2023
Multicomponent
reactions
(MCRs)
have
emerged
as
an
important
branch
in
organic
synthesis
for
the
creation
of
complex
molecular
structures.
This
review
is
focused
on
gold-catalyzed
MCRs
with
a
special
emphasis
recent
developments.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(6), P. 1858 - 1895
Published: Jan. 1, 2024
This
review
is
planned
to
provide
a
comprehensive
overview
of
the
progress
made
in
design
and
development
chiral
ligands
for
asymmetric
gold
catalysis.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
62(3)
Published: Sept. 28, 2022
Abstract
Direct
C−H
bond
functionalization
is
a
useful
strategy
for
the
straightforward
formation
of
C−C
and
C−Heteroatom
bonds.
In
present
work,
unique
approach
challenging
electrophilic
Au‐catalyzed
α
‐
tertiary
amines
presented.
Electronic,
steric
conformational
synergistic
effects
exerted
by
use
malonate
unit
in
substrate
were
key
to
success
this
transformation.
This
new
reactivity
was
applied
synthesis
tetrahydro‐γ‐carboline
products
which,
under
oxidative
conditions,
could
be
converted
into
valuable
structural
motifs
found
bioactive
alkaloid
natural
products.
ACS Sustainable Chemistry & Engineering,
Journal Year:
2022,
Volume and Issue:
10(21), P. 6900 - 6918
Published: May 16, 2022
Gold
catalysis
has
emerged
as
an
efficient
tool
in
the
field
of
synthetic
organic
chemistry.
Despite
significant
progress,
need
for
high
catalyst
loadings
mainly
hampered
its
applicability
large-scale
synthesis.
Recent
research
showcased
importance
ligand
engineering
to
realize
gold-catalyzed
transformations
at
low
loadings,
milder
reactions
conditions,
and
greener
solvents.
In
this
perspective,
we
summarized
reports
that
clearly
emphasize
crucial
role
ligands
achieving
highly
catalysts
(≤0.1
mol
%)
with
turnover
numbers
frequencies.
This
perspective
also
briefly
discusses
challenges
future
potential
development
ppm-level
gold
catalysis.
Natural Product Reports,
Journal Year:
2024,
Volume and Issue:
41(7), P. 1091 - 1112
Published: Jan. 1, 2024
This
review
highlights
a
curated
selection
of
publications
utilizing
homogeneous
gold-catalyzed
cycloaddition
and
cyclization
reactions
for
the
total
synthesis
natural
products
reported
from
2016
to
mid-2023.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(40)
Published: Aug. 4, 2022
Abstract
An
asymmetric
para‐
C(sp
2
)−H
bond
functionalization
of
alkyl
benzene
derivatives
was
successfully
developed
via
cooperative
catalysis
gold
and
chiral
phosphoric
acid
(CPA),
leading
to
synthetically
useful
1,1‐diaryl
motifs.
Chiral
acid,
ligand,
molecular
sieves
were
found
be
crucial
for
enantioselectivity
control
this
transformation.
The
salient
features
protocol
include
mild
conditions,
high
efficiency,
commercially
available
starting
materials,
highly
chemo‐
site‐
as
well
enantioselective
aromatic
C−H
functionalization,
broad
substrate
scope,
extensive
applications
the
products.
mechanistic
studies
suggested
that
two
CPAs
might
involved
in
induction.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(4), P. 2308 - 2312
Published: Jan. 18, 2024
Bifunctional
ligand-enabled
cooperative
gold
catalysis
accelerates
nucleophilic
attacks
and
offers
a
versatile
strategy
to
achieve
asymmetric
catalysis.
Distinct
from
the
prior
studies
employing
alkyne/allene
as
electrophilic
site,
this
work
engages
an
in
situ-generated
alkenyl/acyl
carbene
ligand-facilitated
attack
by
alcoholic
nucleophile.
With
amide-functionalized
chiral
binaphthylphosphine
ligand,
γ-alkoxy-α,β-unsaturated
imides
are
formed
with
excellent
enantiomeric
excesses.
The
intermediacy
of
species
is
supported
its
alternative
access
via
dediazotization.
reaction
tolerates
broad
range
alcohols
can
accommodate
dienynamide
substrates,
addition
arylenynamides.
This
avails
enrich
chemistry
challenging
enantioselective
trapping
reactive
intermediates.
