Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 23, 2025
This
work
demonstrates
Cu–NHC
(NHC
=
N-heterocyclic
carbene)
catalyzed
alkynylation
of
aryl
thianthrenium
salts
via
thiazol-2-ylidene
ligands,
achieving
a
Pd-free
Sonogashira
coupling
with
broad
substrate
compatibility
and
functional
group
tolerance.
Late-stage
pharmaceutical
rare
alkynylative
C–H
functionalization/ring-opening
pathways
are
enabled.
Thiazol-2-ylidenes,
featuring
"half-umbrella"-shaped
geometry,
exhibit
superior
catalytic
performance
over
traditional
imidazol-2-ylidenes,
underscoring
their
unique
ligand
efficacy.
catalysis
enables
the
use
as
versatile
electrophiles
for
diverse
cross-couplings
under
mild
conditions.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
21(5), P. 879 - 909
Published: Dec. 6, 2022
Transition
metal-catalyzed
cross-coupling
of
sp2
C-H
bonds
with
diazo
compounds
via
carbene
migratory
insertion
represents
an
efficient
strategy
for
the
construction
C-C
and
C-heteroatom
in
organic
synthesis.
Despite
popularity
as
coupling
partners
activation,
they
pose
serious
safety
stability
issues
due
to
potential
exothermic
reactions
linked
release
N2
gas.
However,
compared
compounds,
sulfoxonium
ylides
are
generally
crystalline
solids,
more
stable,
widely
used
industrial
scales,
easier/safer
prepare.
Therefore,
recent
years
have
witnessed
upsurge
employing
α-carbonyl
alternative
surrogate
transition
activation.
Unlike
contain
inherent
serve
a
partner
well
weak
directing
group.
This
review
will
summarize
progress
made
both
categories
reactions.
Advanced Synthesis & Catalysis,
Journal Year:
2020,
Volume and Issue:
363(2), P. 446 - 452
Published: Dec. 2, 2020
Abstract
A
formation
of
fused
tricyclic
[1,3]oxazino[3,4‐
a
]indol‐1‐ones
and
dihydropyrimido[1,6‐
]indol‐1(2
H
)‐ones
via
Rh(III)‐catalyzed
[3+3]
or
[4+2]
annulation
N
‐methoxy‐1
‐indole‐1‐carboxamides
with
sulfoxonium
ylides
has
been
developed.
These
selective
reactions
were
carried
out
by
switching
the
additives
notable
features
this
protocol
low
catalyst
loading
broad
substrate
scope
providing
corresponding
products
in
up
to
99%
yields.
magnified
image
Asian Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
10(7), P. 1671 - 1674
Published: April 15, 2021
Abstract
A
rhodium‐catalyzed
synthesis
of
isoquinolino[1,2‐
b
]quinazolines
via
C−H
annulation
using
vinylene
carbonate
as
an
oxidizing
acetylene
surrogate
in
biomass‐derived
γ
‐valerolactone
(GVL)
has
been
developed.
The
reactions
proceeded
smoothly
to
give
the
corresponding
products
moderate
good
yields
without
any
external
oxidant
and
base.
This
protocol
can
also
be
applied
for
5,6‐dihydro‐8
H
‐isoquinolino[1,2‐
]quinazolin‐8‐ones.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(13), P. 3311 - 3317
Published: May 8, 2021
Abstract
A
method
to
synthesize
pyrazolo[1,2‐a]cinnolines
via
rhodium(III)‐catalyzed
C−H
activation
of
pyrazolidinones
and
subsequent
[4+2]
annulation
sulfoxonium
ylides
was
developed.
5‐Substituted
or
5,10‐disubstituted
could
be
obtained
by
slightly
adjusting
the
reaction
conditions.
Gram‐scale
synthesis
practical
transformations
proved
practicability
this
method.
The
mechanism
proposed
in
article
on
basis
preliminary
mechanistic
results
previous
reports.
This
features
simplified
operation,
metal‐oxidant
free,
readily
available
reactants.
magnified
image
Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(6), P. 1190 - 1196
Published: Jan. 1, 2021
Rh(iii)-Catalyzed
C–H
activation/annulation
of
N-iminopyridinium
ylides
with
alkynes
and
diazo
compounds
has
been
realized
for
the
synthesis
isoquinolones
isocoumarins.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(13), P. 2248 - 2254
Published: May 27, 2023
Abstract
Herein,
an
eco‐friendly
and
atom‐economical
electrochemical
methodology
with
isatins
1,2,3,4‐tetrahydroisoquinolines
through
NHPI/O
2
‐mediated
intermolecular
oxidation/annulation
is
disclosed,
leading
to
a
variety
of
polycyclic
quinazolinones
in
46–82%
yields.
This
oxidative
cyclization
proceeded
transition
metal‐
strong
oxidant‐free
conditions
generated
H
CO
as
byproducts.
Additionally,
late‐stage
functionalization
broad
substrate
scope
demonstrated
the
synthetic
usefulness
this
protocol.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(8), P. 1863 - 1876
Published: Feb. 21, 2024
Abstract
Ru(II)‐catalyzed
and
solvent‐switched
[3+2]‐spiroannulation
[4+n]
(n=1,
2,
3)
annulations
of
2‐aryl
quinazolinone
or
2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones
with
ynones
alkynyl
alcohol
1,3‐diynes
under
mild
reaction
conditions
have
been
analyzed.
These
reactions
take
place
in
the
presence
appropriate
solvent
features
a
redox‐neutral
pathway.
Ynone
serves
as
an
‘atypical
one‐carbon
unit’
[4+1]
annulation
generates
tetrasubstituted
carbon
center
bearing
diverse
heterocycles
through
[3+2]
strategies.
Post
transformations
synthesized
spiro‐products
augments
potential
developed
methodology.
Chinese Journal of Chemistry,
Journal Year:
2020,
Volume and Issue:
38(11), P. 1239 - 1244
Published: May 17, 2020
Summary
of
main
observation
and
conclusion
Polycyclic
fused
quinazolinones
with
anti‐malarial
activity
were
synthesized
through
tert
‐butyl
hydroperoxide
(TBHP)‐mediated
oxidative
decarboxylative
cyclization
between
commercially
available
isatins
cyclic
amines
in
one
step.
The
reaction
proceeds
smoothly
water
without
additional
transition‐metal
catalyst,
acid
base.
newly
products
evaluated
to
exhibit
moderate
good
against
chloroquine
drug‐sensitive
Plasmodium
falciparum
3D7
strain.
Additionally,
this
method
also
provides
direct
approach
Rutaecarpine
yield.
