Physical Chemistry Chemical Physics,
Год журнала:
2020,
Номер
22(35), С. 19606 - 19612
Опубликована: Янв. 1, 2020
We
herein
report
a
computational
study
of
the
hydrogen
bonding
in
gold-catalyzed
ipso-cyclization
to
diverse
polyheterocyclic
frameworks.
The
different
roles
these
bonds
are
analyzed
for
reactions.
fine-tunability
electronic
as
well
steric
properties
gold
counterions
contributed
substantially
popularity
dearomatization
reaction,
with
robust
applications
total
synthesis
and
catalysis.
have
found
correlation
between
parameters
chemoselectivity
spirocyclization,
playing
critical
determining
reaction
direction
counterion-based
enantioselective
expanded
use
via
interaction
can
occupy
an
important
role
future
concerning
catalyst
optimization
Chemical Reviews,
Год журнала:
2020,
Номер
121(14), С. 8756 - 8867
Опубликована: Ноя. 23, 2020
This
review
describes
the
gold-catalyzed
reactions
of
specially
activated
alkynes,
allenes,
and
alkenes.
Such
species
are
characterized
by
presence
either
electron-donating
or
electron-withdrawing
groups
as
substituents
carbon
π-system.
They
intrinsically
polarized,
when
compared
to
their
nonspecially
counterparts
can
therefore
be
involved
in
transformations
featuring
increased
regio-,
stereo-,
chemoselectivities.
The
chemistry
π-systems
under
homogeneous
gold
catalysis
is
extremely
rich
varied.
reactivity
observed
with
unsaturated
systems
often
transposed
ones
without
loss
efficiency.
However,
also
exhibit
specific
reactivities
that
cannot
attained
regular
substrates.
In
this
family
π-systems,
ynamides
analogs,
along
alkynyl
carbonyl
derivatives,
classes
substrates
have
retained
most
attention.
provides
an
overview
developed
all
discussing
general
reactivities,
presenting
commenting
on
well
applications.
The Chemical Record,
Год журнала:
2021,
Номер
21(12), С. 4123 - 4149
Опубликована: Авг. 25, 2021
Ynamide,
a
unique
species
with
inherited
polarization
of
nitrogen
lone
pair
electron
to
triple
bond,
has
been
largely
used
for
the
developement
novel
synthetic
methods
and
construction
unusual
N-bearing
heterocycles.
The
reaction
versatility
ynamide
on
umpolung
reactivity,
radical
reactions
asymmetric
synthesis
have
recently
reviewed.
This
review
provides
an
overall
scenic
view
into
gold
catalyzed
transformation
ynamides.
ynamides
reactivity
towards
nitrogen-transfer
reagents,
such
as
azides,
ylides,
isoxazoles,
anthranils;
oxygen
atom-transfer
like
nitrones,
sulfoxides,
pyridine
N-oxides;
carbon
nucleophiles
under
catalysis
are
herein
uncovered.
scope
well
mechanistic
insights
each
is
also
briefed.
Organic Letters,
Год журнала:
2020,
Номер
22(19), С. 7681 - 7687
Опубликована: Сен. 11, 2020
Skipped
diynones,
efficiently
prepared
from
biomass-derived
ethyl
lactate,
undergo
a
tandem
hydration–oxacyclization
reaction
under
gold(I)
catalysis.
Reaction
conditions
have
been
developed
for
switchable
process
that
allows
selective
access
to
4-pyrones
or
3(2H)-furanones
the
same
starting
diynones.
Further
application
of
this
methodology
in
total
synthesis
polyporapyranone
B
was
demonstrated.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(36), С. 7151 - 7187
Опубликована: Янв. 1, 2022
Gold-catalyzed
hydroarylation
reaction
offers
new
pathways
for
producing
complex
organic
compounds
with
diverse
ring
sizes
in
a
highly
regio-
and
stereo-selective
approach
from
available
precursors
like
olefins,
alkynes,
arenes,
aryl
halides.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 27, 2025
A
mild
CuI-catalyzed
dearomatization/peroxidation/cyclization
cascade
of
pyrrole-tethered
indoles
has
been
reached,
providing
peroxide-incorporated
indolizino[8,7-b]indole
derivatives
in
acceptable
to
good
yields
(46–76%).
Dehydrogenated
peroxide
can
be
obtained
by
the
use
a
FeCl3/TBHP
(tBuOOH)/2,2,2-trifluoroethanol
(TFE)
system
at
50
°C.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 10, 2025
An
NIS-promoted
cascade
of
intramolecular
C-N
bond
formation/aromatization
with
3-(1H-indol-3-yl)-2-(pyridin-2-yl)propanoates
is
described
for
synthesizing
a
polycyclic
indole
skeleton,
indolo[3,2-c]quinolizine,
as
well
1,9-dihydropyrazolo[4',3':5,6]pyrido[2,3-b]indole.
The
advantages
this
protocol
include
accessible
starting
materials,
mild
conditions,
simple
operation,
and
good
yields.
Indolo[3,2-c]quinolizines
exhibited
fluorescence
properties
effective
staining
live
cells,
targeting
lysosomes
mitochondria.
Additionally,
the
products
showed
significant
antiproliferative
activity
against
tumor
cells
in
MTT
assay.
Chemistry - A European Journal,
Год журнала:
2020,
Номер
27(4), С. 1165 - 1218
Опубликована: Июнь 30, 2020
Heteroarene-tethered
functionalized
alkynes
are
multipotent
synthons
in
organic
chemistry.
This
detailed
Review
described
herein
offers
a
thorough
discussion
of
the
metamorphosis
heteroarene-tethered
alkynes,
an
area
which
has
earned
much
attention
over
past
decade
straightforward
synthesis
architecturally
complex
heterocyclic
scaffolds
atom
and
step
economic
manner.
Depending
upon
variety
this
is
divided
into
multiple
sections.
Amongst
vast
array
synthetic
transformations
covered,
dearomatizing
spirocyclizations
cascade
spirocyclization/rearrangement
great
interest.
Synthetic
involving
with
scope,
challenges,
limitations,
mechanism,
their
application
total
natural
products
future
perceptions
surveyed.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
62(8)
Опубликована: Дек. 27, 2022
Herein,
an
I2
-catalyzed
unprecedented
cycloisomerization
of
ynamides
is
developed,
furnishing
various
functionalized
bis(indole)
derivatives
in
generally
good
to
excellent
yields
with
wide
substrate
scope
and
atom-economy.
This
protocol
not
only
represents
the
first
molecular-iodine-catalyzed
tandem
complex
alkyne
cycloisomerizations,
but
also
constitutes
chemoselective
tryptamine-ynamides
involving
distinctively
different
C(sp3
)-C(sp3
)
bond
cleavage
rearrangement.
Moreover,
chiral
tetrahydropyridine
frameworks
containing
two
stereocenters
are
obtained
moderate
diastereoselectivities
enantioselectivities.
Meanwhile,
aromatization
produce
pyrrolyl
indoles
high
efficiency
enabled
by
.
Additionally,
control
experiments
theoretical
calculations
reveal
that
this
reaction
probably
undergoes
a
5-exo-dig
cyclization/rearrangement
process.
Chemical Communications,
Год журнала:
2022,
Номер
58(18), С. 3051 - 3054
Опубликована: Янв. 1, 2022
A
Ag(I)/PPh3-catalyzed
chelation-controlled
cycloisomerization
of
tryptamine-ynamide
was
developed
to
access
the
spiro[indole-3,4'-piperidine]
scaffold
in
a
racemic
and
diastereoselective
manner.
The
products
were
achieved
by
chiron
approach.
Density
functional
theory
(DFT)
calculations
indicated
that
strong
non-covalent
effects
between
substrate
catalyst/ligand
complex
stabilized
spiroindoleninium
intermediate
via
cation-π-π
interactions.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(16), С. 3276 - 3295
Опубликована: Янв. 1, 2023
This
review
focuses
on
recent
advancements
in
the
efficacy
of
gold
catalysts
for
cycloisomerisation
ynamides,
diynes,
and
1,
n
-enynes
to
build
complex
molecules,
with
critical
insight
into
their
mechanism
reaction
scope.
