Catalyst‐Free Direct Hydrocarbonation of Terminal Alkynes Toward E‐Alkene Substituted Stabilized Sulfoxonium Ylides
Haiting Wu,
Yougen Xu,
Lin An
и другие.
Advanced Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 2, 2025
Amide
and
alkene
moieties
are
frequently
found
in
natural
products
privileged
structures
pharmaceuticals
agrochemicals.
Moreover,
vinyl
sulfoxonium
ylide
can
be
converted
into
a
broad
range
of
high-value
compounds,
thus
they
have
been
widely
employed
organic
synthesis.
However,
the
synthesis
alkene-substituted
amide-sulfoxonium
ylides
via
intermolecular
hydrocarbonation
alkynes
remains
underexplored.
This
study
describes
development
high-throughput
approach
to
provide
diverse
functionalized
E-alkene
substituted
(hetero)amide-sulfoxonium
ylides.
The
reaction
occurs
under
mild
metal-free
conditions,
employing
as
highly
effective
nucleophiles,
which
participate
Michael
addition
reactions
with
various
alkynes,
such
esters,
thioesters,
ketones,
amides,
sulfones.
low-cost,
operationally
simple
has
substrate
scope,
high
functional
group
compatibility,
excellent
regio-
stereoselectivity,
making
it
suitable
for
transformation
structurally
complex
molecules.
Furthermore,
obtained
stabilized
directly
useful
valuable
1,5-dicarbonyl
thiabenzene
1-oxide
compounds.
Язык: Английский
Light-induced β-hydroxy sulfone synthesis in DNA-encoded libraries
Chemical Communications,
Год журнала:
2024,
Номер
60(54), С. 6885 - 6888
Опубликована: Янв. 1, 2024
We
here
describe
a
visible-light
photooxidation
of
sulfinate
salts
with
common
alkenes
to
yield
β-hydroxy
sulfones
on
DNA.
This
process
demonstrates
broad
substrate
compatibility
and
achieves
conversion
rates
ranging
from
moderate
excellent.
Most
importantly,
it
presents
straightforward,
efficient,
metal-free
approach
for
synthesizing
Csp
Язык: Английский
Regioselective Synthesis of N-Aryl Pyrazoles from Alkenyl Sulfoxonium Ylides and Aryl Diazonium Salts
Ramesh Kumar Vishwakarma,
Raju Sen,
Shalu Deshwal
и другие.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 2, 2024
A
convenient
and
practical
method
has
been
developed
for
synthesizing
various
N-aryl
pyrazoles
from
vinyl
sulfoxonium
ylides
diazonium
salts.
When
using
1,3-disubstituted
ylides,
the
reaction
selectively
yields
1,3,5-trisubstituted
pyrazoles.
On
other
hand,
employing
2,3-disubstituted
results
in
formation
of
1,3,4-trisubstituted
The
proceeds
through
novel
aryl
diazene-derived
ylide.
Furthermore,
this
efficiently
produces
aniline
derivatives
a
one-pot
transformation.
takes
place
under
transition
metal-free,
mild
conditions
easily
accessible
starting
materials,
making
it
approach
generating
pharmaceutical
chemistry.
Язык: Английский
Gold‐Catalyzed Diyne‐Ene Annulation for the Synthesis of Polysubstituted Benzenes through Formal [3+3] Approach with Amide as the Critical Co‐Catalyst
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 21, 2024
The
one-step
synthesis
of
tetra-substituted
benzenes
was
accomplished
via
gold-catalyzed
diyne-ene
annulation.
Distinguished
from
prior
modification
methods,
this
novel
strategy
undergoes
formal
[3+3]
cyclization,
producing
polysubstituted
with
exceptional
efficiency.
critical
factor
enabling
transformation
the
introduction
amides,
which
were
reported
for
first
time
in
gold
catalysis
as
covalent
nucleophilic
co-catalysts.
This
interesting
protocol
not
only
offers
a
new
to
achieve
functional
high
efficiency,
but
also
enlightens
potential
reaction
pathways
within
alkyne
activation
processes.
Язык: Английский
Diastereoselective Cyclopropanation of α,β- Unsaturated Carbonyl Compounds with Vinyl Sulfoxonium Ylides
Shalu Deshwal,
Dinesh Kumar Gopalakrishnan,
Alok Purohit
и другие.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(31), С. 6294 - 6307
Опубликована: Янв. 1, 2024
Vinyl
cyclopropane
scaffolds
were
synthesized
via
a
proline-catalysed
multicomponent
reaction
involving
vinyl
sulfoxonium
ylides,
aldehydes,
and
indane
1,3-dione.
Язык: Английский
Recent approaches for the synthesis of heterocycles from amidines via metal catalyzed C-H functionalization reaction
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(25), С. 5014 - 5031
Опубликована: Янв. 1, 2024
Transition
metal
catalyzed
C-H
bond
activation
has
become
one
of
the
most
important
tools
for
constructing
new
chemical
bonds.
Introducing
directing
groups
to
substrates
is
key
a
successful
reaction,
these
can
also
be
further
transformed
in
reaction.
Amidines
with
their
unique
structure
and
reactivity
are
ideal
transition
metal-catalyzed
transformations.
This
review
describes
major
advances
mechanistic
investigations
activation/annulation
tandem
reactions
amidines
until
early
2024,
focusing
on
unsaturated
compounds,
such
as
alkynes,
ketone,
vinylene
carbonate,
cyclopropanols
derivatives.
Meanwhile
this
manuscript
explores
reaction
different
carbene
precursors,
example
diazo
azide,
triazoles,
pyriodotriazoles,
sulfoxonium
ylides
well
own
activation/cyclization
reactions.
A
bright
outlook
provided
at
end
manuscript.
Язык: Английский
Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 25, 2024
Carbene-catalyzed
[3
+
3]
annulation
of
enals
and
vinyl
sulfoxonium
ylides
has
been
demonstrated.
This
method
efficiently
synthesizes
a
range
2-sulfenylidene-3-cyclohexen-1-ones
with
high
atom
economy.
Notably,
the
presence
ylide
moiety
in
obtained
products
significantly
enhances
their
potential
for
further
synthetic
transformations.
Язык: Английский
Visible-Light-Mediated gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols
Synthesis,
Год журнала:
2024,
Номер
unknown
Опубликована: Июнь 21, 2024
Abstract
A
visible-light-induced
multicomponent
reaction
of
vinyl
sulfoxonium
ylide,
thiol,
and
diazo
ester
to
generate
tertiary
sulfide
is
described.
The
present
diastereoselective
gem-difunctionalization
the
can
be
achieved
under
mild
conditions,
as
it
does
not
require
any
additives,
catalysts,
or
transition
metals
tolerant
air
moisture.
Due
more
nucleophilicity,
ylide
undergoes
S–H
insertion
with
thiols
an
allyl
intermediate.
Simultaneously,
photolysis
a
carbene
Subsequently,
coupling
intermediates
generates
sulfonium
which
Doyle–Kirmse
rearrangement
scaffolds.
Язык: Английский
Gold‐Catalyzed Diyne‐Ene Annulation for the Synthesis of Polysubstituted Benzenes through Formal [3+3] Approach with Amide as the Critical Co‐Catalyst
Angewandte Chemie,
Год журнала:
2024,
Номер
136(39)
Опубликована: Июль 8, 2024
Abstract
The
one‐step
synthesis
of
tetra‐substituted
benzenes
was
accomplished
via
gold‐catalyzed
diyne‐ene
annulation.
Distinguished
from
prior
modification
methods,
this
novel
strategy
undergoes
formal
[3+3]
cyclization,
producing
polysubstituted
with
exceptional
efficiency.
critical
factor
enabling
transformation
the
introduction
amides,
which
were
reported
for
first
time
in
gold
catalysis
as
covalent
nucleophilic
co‐catalysts.
This
interesting
protocol
not
only
offers
a
new
to
achieve
functional
high
efficiency,
but
also
enlightens
potential
reaction
pathways
within
alkyne
activation
processes.
Язык: Английский