Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(29), P. 6263 - 6268
Published: July 12, 2024
A
metal-free
cascade
of
α-acyloxylation/carboxamidation
I(III)/S(VI)-ylides,
carboxylic
acids,
and
isonitriles
via
a
Passerini-like
multicomponent
reaction
is
reported.
Unexpectedly,
[3
+
1+1]
cyclization
involving
I(III)/S(VI)-ylides
two
molecules
ethyl
isocyanoacetate
was
observed.
The
strategy
allows
for
the
synthesis
unsymmetrical
α,α-disubstituted
ketones
functionalized
pyrroles
with
up
to
99%
yield
wide
substrate
compatibility.
Notably,
procedure
has
been
extended
late-stage
modification
drugs
natural
products,
offering
an
elegant
complement
classic
Passerini
reaction.
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(4)
Published: March 23, 2022
Abstract
In
recent
years,
the
transition‐metal‐catalyzed
functionalization
reactions
of
sulfoxonium
ylides
have
been
explored
extensively
because
their
usefulness
as
carbene‐transfer
agents,
since
they
can
produce
metal
carbenes
through
catalysis.
Moreover,
are
safer
and
advantages
simple
handling
good
stability
over
other
counterparts
like
diazo‐compounds.
This
review
article
attempts
to
highlight
advances
in
metal‐catalyzed
C−H
ylides.
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(4), P. 2330 - 2347
Published: Feb. 1, 2022
Transition-metal-catalyzed
alkylation
of
(hetero)arenes
with
three-membered
carbo-/heterocycles
involving
C–H
activation
and
ring
scission
has
been
greatly
developed
over
the
past
few
years.
The
chelation-assisted
strategies
for
controlling
reactivity
site
selectivity
in
these
protocols
include
use
nitrogen-containing
directing
groups,
pre-existing
functional
a
Catellani-type
intermediate,
thereby
providing
rapid
access
to
numerous
oxygen-
or
heterocyclic
systems.
This
review
gives
an
update
area
various
catalytic
methodologies
applications
total
synthesis
natural
products
rings
as
alkylating
reagents,
which
are
classified
into
following
three
categories
on
basis
employed
strategies:
(i)
directed
by
(ii)
(iii)
aryl-NBE
intermediates
(Catellani-type
cascade
reaction).
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(23), P. 4286 - 4291
Published: June 2, 2023
Two
categories
of
tetrasubstituted
phenols
were
prepared
via
the
cycloaddition
reaction
vinyl
sulfoxonnium
ylides
with
cyclopropenones
in
a
switchable
manner.
Copper
carbenoid
was
proposed
as
active
intermediate
process
2,3,4,5-tetrasubstituted
formation,
while
2,3,5,6-tetrasubstituted
generated
direct
[3
+
3]
annulation
under
metal-free
conditions.
Further
synthetic
applications
also
demonstrated.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(15), P. 3843 - 3848
Published: Jan. 1, 2023
We
have
developed
a
Rh(
iii
)-catalyzed
C–H
activation/chemodivergent
annulation
of
N
-carbamoylindoles
with
TFISYs,
allowing
facile
access
to
variety
trifluoromethyl-substituted
(dihydro)pyrimidoindolones
high
efficiency.
Solvents
play
critical
role
in
the
selectivity
reaction.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(9), P. 5572 - 5585
Published: April 21, 2023
Organoselenium
compounds
are
important
scaffolds
in
pharmaceutical
molecules.
Herein,
we
report
metal-free,
electrochemical,
highly
chemo-
and
regioselective
synthesis
of
gem-diselenides
through
the
coupling
α-keto
sulfoxonium
ylides
with
diselenides.
The
versatility
electrochemical
manifold
enabled
selenylation
ample
scope
broad
functional
group
tolerance,
as
well
setting
stage
for
modification
complex
bioactive
Detailed
mechanistic
studies
revealed
that
key
C-Se
bond
was
constructed
using
n-Bu4NI
an
electrolyte
catalyst
electrosynthetic
protocol.
Finally,
desired
showed
excellent
antimicrobial
activity
against
Candida
albicans,
which
can
be
identified
lead
further
exploration.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(11), P. 3234 - 3241
Published: Jan. 1, 2024
Herein,
we
present
a
cascade
O–H
double
insertion
reaction
between
I
(III)
/S
(VI)
-ylides,
carboxylic
acids,
and
alcohols
under
metal-free
conditions,
enabling
the
modular
synthesis
of
unsymmetrical
α,α-
O
,
-substituted
ketones.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(9), P. 1457 - 1464
Published: April 14, 2023
Abstract
In
this
study,
Rh(III)‐catalyzed
C−H
bifunctionalization
and
direct
vinylene
annulation
of
sulfoxonium
ylides
N
‐carbamoylindoles
with
carbonate
was
accomplished,
which
afforded
a
series
naphthalenones
containing
β‐ketosulfoxonium
ylide
moiety,
isocoumarins,
pyrimidones.
This
protocol
featured
mild
conditions,
broad
substrate
scope,
functional‐groups
compatibility.
addition,
related
applications
preliminary
mechanistic
exploratory
were
also
investigated
magnified
image
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(8), P. 1744 - 1750
Published: Feb. 22, 2024
Abstract
The
transmetalation
triggered
rhodium‐catalyzed
C−H
bond
activation
and
tandem
annulation
of
2‐biphenylboronic
acids
with
sulfoxonium
ylides
or
iodonium
has
been
developed.
Various
products
phenanthrenes
were
constructed
under
redox‐neutral
conditions
in
34–86%
yields.
Several
mechanism
exploration
experiments
derivatization
reactions
conducted
sequence
to
gain
a
deeper
understanding
the
process
potential
this
transformation.
It
offers
an
alternative
approach
for
synthesis
phenanthrene
derivatives.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(15), P. 5719 - 5723
Published: July 21, 2021
A
rhodium(III)-catalyzed
C-H
allylation
of
(hetero)arenes
by
using
2-methylidenetrimethylene
carbonate
as
an
efficient
allylic
source
has
been
developed
for
the
first
time.
Five
different
directing
groups
including
oxime,
N-nitroso,
purine,
pyridine,
and
pyrimidine
were
compatible,
delivering
various
branched
allylarenes
bearing
hydroxyl
group
in
moderate
to
excellent
yields.
