Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(43), P. 9401 - 9406
Published: Oct. 22, 2024
An
operationally
simple
and
highly
efficient
synthesis
of
functionalized
thiophenes
has
been
developed
by
LiBr
promoted
heteroannulation
β-ketodithioesters
thioamides
with
bench-stable
sulfoxonium
ylides
in
open
air
for
the
first
time.
This
one-pot
strategy
involves
formal
Csp3–H
bond
insertion/intramolecular
cyclization
cascade,
featuring
readily
accessible
starting
materials,
TM
additive-free
condition,
broad
substrate
scope,
high
functional
group
compatibility,
scalability.
Moreover,
carbonyl,
thiomethyl,
amino
groups
resulting
thiophene
provide
a
good
handle
on
downstream
transformations.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(6), P. 1220 - 1268
Published: Jan. 22, 2024
Abstract
Elaborated
molecular
architectures,
specifically
those
bearing
one
or
more
carbon
stereocenters,
stand
as
an
important
class
of
carbocyclic
and
heterocyclic
frameworks
because
they
are
frequently
occurring
core
structures
in
numerous
natural
products
biologically
active
pharmaceutical
molecules.
Over
the
past
few
decades,
development
versatile
synthetic
approaches
via
cascade
cyclization
reactions
1,6‐enynes
for
construction
a
series
fused
spiro
compounds
has
been
focus
great
deal
research
initiatives.
These
synthesis
strategies
peculiarly
fascinating
context
assembly
wide
array
molecules,
products,
agrochemicals,
functional
materials.
In
this
review,
recent
developments
transformations
with
diverse
coupling
reagents
summarized
since
2018,
which
could
be
divided
into
five
categories:
1)
Introduction;
2)
Transition
metal
catalyzed
1,6‐enynes;
3)
Metal‐free
4)
Visible‐light‐induced
5)
Electrocatalytic
1,6‐enynes.
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.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(10)
Published: Jan. 9, 2024
Abstract
We
present
the
first
example
of
electrocatalytic
three‐component
annulation–iodosulfonylation
indole‐tethered
1,6‐enynes
with
arylsulfonyl
hydrazides
and
KI
for
accessing
various
iodosulfonated
pyrrolo[1,2‐
a
]indoles
in
moderate
to
excellent
yields
high
stereospecificity.
This
electrosynthesis
opens
new
avenues
construction
skeleton
good
functional
group
compatibility
under
environmentally
benign
condition.
Based
on
control
experiments
cyclic
voltammetry
data,
we
suggested
plausible
reaction
mechanism
which
included
anodic
oxidation,
homolysis
iodide,
radical
addition,
5
‐
exo
dig
cyclization,
coupling
or
nucleophilic
attack
iodide
ions
cascade.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(27), P. 5811 - 5816
Published: June 28, 2024
A
practical
strategy
for
the
construction
of
diverse
phosphonyl
and
thiofunctionalized
sulfoxonium
ylides
via
controllable
monofunctionalization
hybrid
I(III)/S(VI)
is
presented.
This
process
allows
efficient
P–H
insertion
under
Cu
catalysis,
enabling
synthesis
ylides,
whereas
reaction
with
sulfur-containing
reagents
including
AgSCF3,
KSC(S)OR,
KSCN
mild
conditions
resulted
in
α-trifluoromethylthiolation,
dithiocarbanation,
thiocyanation
accordingly.
Of
note,
wide
substrate
compatibility
(108
examples),
excellent
efficiency
(up
to
99%
yield),
gram-scale
experiments,
various
product
derivatizations
highlight
synthetic
utility
this
protocol.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
A
metal-free
protocol
for
the
modular
synthesis
of
diverse
α-thiofunctionalized-α′-carbonyl
sulfoxonium
ylides
from
sulfoxonium–iodonium
hybrid
(I
(III)
/S
(VI)
-ylides)
has
been
achieved.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(10), P. 6974 - 6986
Published: May 4, 2024
A
LiBr-promoted
formal
C(sp3)–H
bond
insertion
reaction
between
β-carbonyl
esters
and
sulfoxonium
ylides
is
established.
This
practical
has
a
wide
range
of
substrate
scope
for
both
to
give
variety
1,4-dicarbonyl
compounds
with
43–94%
yields.
The
features
transition-metal-free
conditions
exclusive
C-alkylation
chemselectivity.
use
bench-stable
overcomes
previous
methods
that
require
transition
metal
as
catalysts
unstable
diazo
or
toxic
haloketones
alkylation
reagents.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(28), P. 5940 - 5945
Published: July 11, 2024
The
most
convenient
and
direct
method
of
synthesizing
an
α-acyloxy
ketone
is
the
reaction
a
diazo
compound
with
carboxylic
acid
via
O-H
insertion.
However,
due
to
limitations
in
preparing
storing
compounds,
application
this
restricted.
In
study,
Cu(OAc)
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(4), P. 463 - 468
Published: Jan. 13, 2023
Abstract
A
three
component
construction
of
conjugated
1,3‐dienes
bearing
oxindoles
or
isoquinolinediones
from
alkenylated
aryl
iodides,
allenes
and
diazo
compounds
via
a
palladium
catalyzed
sequential
alkene/allene/carbenoid
insertion
reaction
was
developed.
Three
C−C
bonds
were
formed
in
high
order,
offering
access
to
multi‐substituted
dienes
yields
up
>20:1
E/Z
selectivities.
The
features
excellent
functional
groups
tolerance
under
mild
conditions.
magnified
image
