Catalysts,
Journal Year:
2023,
Volume and Issue:
13(7), P. 1051 - 1051
Published: June 29, 2023
In
this
paper,
A
new
gold
self-relay
catalysis
enabling
intramolecular
annulation
and
intermolecular
Michael
addition
of
3-yne-1,2-diols
with
aurone-derived
azadienes
(or
para-quinone
methides)
is
reported,
efficiently
furnishing
a
range
unsymmetrical
furanized
triarylmethanes
substituent
diversity
in
good
yields.
The
overall
process
was
governed
by
the
π-
σ-Lewis
acid
capability
complexes,
providing
catalytic
strategy
for
constructing
triarylmethane
skeletons.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(18), P. 2991 - 3019
Published: July 14, 2023
Abstract
Propargylic
alcohols
are
readily
available
bifunctional
(alkyne
and
hydroxyl
groups)
synthons,
which
recognize
as
one
of
the
attractive
synthetic
feedstock
in
organic
transformations.
Especially,
recent
years
employment
these
valuable
molecules
has
frequently
been
observed
literature.
Hence,
present
review
highlights
advancements
application
propargylic
cyclization,
substitution,
addition
reactions.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(4), P. 780 - 789
Published: Jan. 5, 2024
Abstract
The
functional
group
compatibility
of
our
recently
disclosed
gold(I)‐catalyzed
cycloisomerization
1‐bromoalkynes
is
studied
in
detail.
Two
main
features
are
addressed,
the
minimum
distances
at
which
polar
groups
tolerated
and
influence
both
electronic
steric
effects
on
performance
aryl
ether
derivatives.
Moreover,
robustness
assessment
experiments
have
been
carried
out
shedding
light
factors
dictating
tolerance.
In
addition,
reaction
has
applied
to
synthesis
a
key
intermediate
total
natural
product
heterobifunctional
molecule.
DFT
calculations
shed
mechanistic
behind
observed
reactivity
trends.
On
one
hand,
destabilization
TS
by
proximity
may
hamper
for
proximal
groups.
other
some
not
regardless
their
position
due
preferential
coordination
gold
oxygen
atom
over
alkyne,
resulting
presumably
competitive
catalyst
deactivation
pathways.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(38), P. 5725 - 5728
Published: Jan. 1, 2023
A
novel
gold(I)/Brønsted
acid
relay
catalysis
enabling
azofuran
activation
to
induce
annulative
rearrangement
from
3-yne-1,2-diols
and
aryldiazonium
tetrafluoroborates
is
reported,
producing
a
series
of
furan-2-yl-substituted
pyrrol-2-ones
bearing
quaternary
carbon
center
with
good
yields.
Exchanging
tetrafluoroborate
for
led
skeletally
identical
but
substituent-diverse
furan-2-yl-containing
yields,
supporting
the
key
by
gold/Brønsted
catalysis.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(12), P. 8734 - 8744
Published: May 30, 2024
A
gold-catalyzed
oxidative
rearrangement
of
propargyl
alcohols,
derived
from
commercially
available
cyclohex-2-en-1-ones
and
alkynes,
was
successfully
developed
for
the
efficient
synthesis
seven-membered
rings.
Thorough
investigations
were
conducted
to
optimize
reaction
conditions
evaluate
its
compatibility
with
various
functional
groups.
Additionally,
this
methodology
applied
formal
total
guanacastepene
A,
demonstrating
practical
utility
in
complex
natural
product
synthesis.
This
versatile
approach
opens
up
new
possibilities
construction
diverse
ring
systems,
providing
valuable
building
blocks
further
exploration
drug
discovery
intricate
molecules.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14571 - 14586
Published: Oct. 4, 2023
An
efficient
and
practical
cascade
cyclization
of
1,5-diynols
with
(RO)2P(O)SH
as
the
acid
promoter
nucleophile
under
mild
conditions
was
developed.
A
variety
highly
substituted
benzo[b]fluorenyl-containing
S-alkyl
phosphorothioates
were
successfully
constructed
in
moderate
to
excellent
yields.
Furthermore,
this
protocol
exhibited
good
functional
group
tolerance,
a
broad
substrate
scope,
potential
applications,
water
only
byproduct.
The
reaction
proceeded
allenyl
thiophosphate
key
intermediate,
followed
by
Schmittel-type
process
produce
target
product.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(22), P. 16828 - 16837
Published: Oct. 30, 2024
The
distinctive
features
of
gold
self-relay
catalysts
were
alternatively
utilized
in
the
intriguing
cascade
condensation
2-aminobenzaldehydes
with
alcohols
and
amines.
Using
NaAuCl4·2H2O
as
a
catalyst,
range
13-alkyloxy-7,11b-dihydro-6H,13H-6,12-[1,2]benzenoquinazolino[3,4-a]quinazoline
derivatives
was
produced
good
to
high
yields
through
A3B
various
alcohols.
By
carefully
choosing
reaction
conditions,
catalysis
also
proved
effective
for
A2B
primary
aryl-
benzylamines,
facilitating
synthesis
challenging
McGeachin
bisaminals,
including
chiral
nonracemic
derivative
2-(S)-methylbenzylamine.
mild
conditions
this
gold-catalyzed
approach
may
lead
new
advancements
field.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 10, 2024
Despite
both
fluoroalkylsulfonyl
groups
and
benzofurans
are
important
bioactive
moieties,
the
construction
of
fluoroalkanesulfonylated
that
incorporate
these
two
fragments
remains
underdeveloped.
Here,
we
report
a
tandem
cyclization
protocol
to
construct
wide
range
3-fluoroalkylsulfonyl
using
readily
accessible
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(22), P. 16007 - 16017
Published: Oct. 31, 2023
An
elegant
Lewis
acid
catalyzed,
protection-free,
and
straightforward
synthetic
strategy
for
the
assembly
of
a
series
sophisticated
polycyclic
quinoline
skeletons
employing
propargylic
alcohols
2-vinylanilines
as
substrates
in
presence
Yb(OTf)3
(10
mol
%)
AgOTf
tetrahydrofuran
has
been
described.
This
annulation
protocol,
which
proceeds
through
sequential
Meyer-Schuster
rearrangement/nucleophilic
substitution/deprotonation
sequence,
provides
versatile,
practical,
atom-economical
approach
accessing
derivatives
moderate-to-good
yields.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(21), P. 15447 - 15458
Published: Oct. 16, 2024
A
gold
self-relay
catalysis
driving
a
double
annulation
cascade
starting
from
soft
electron-biased
1,2-di(o-aminoaryl)alkynes
and
aldehydes
is
reported,
enabling
regioselective
access
to
produce
series
of
[5]azahelicenes
depending
on
the
substitution
pattern
in
generally
good
yields
under
mild
conditions.
This
protocol
exploits
unifies
π-
σ-Lewis
acid
capability
catalysts,
featuring
high
molecular
convergence,
broad
substrate
flexibility,
functional
group
compatibility
regioselectivity.
