Catalyst-Controlled Divergent Synthesis of 2H-Chromenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Quinones
Shalu Deshwal,
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Daksh Singh Davas,
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Srashti Bhardwaj
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(4), P. 809 - 813
Published: Jan. 23, 2024
Herein,
we
report
the
synthesis
of
2H-chromenes
via
catalyst-controlled
highly
regioselective
[3
+
3]
annulation
vinyl
sulfoxonium
ylides
with
quinones.
Under
boron-catalyzed
conditions,
reaction
between
ylide
and
quinone
resulted
in
formation
2H-chromene-4-carboxylates.
In
contrast,
a
different
mechanistic
pathway
was
observed
when
utilizing
Ru(II)
catalytic
system,
which
led
to
2H-chromene-2-carboxylates
through
furan
intermediate.
Language: Английский
Visible Light-Promoted Regioselective Benzannulation of Vinyl Sulfoxonium Ylides with Ynoates
Daksh Singh Davas,
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Dinesh Kumar Gopalakrishnan,
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Sandeep Kumar
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et al.
JACS Au,
Journal Year:
2024,
Volume and Issue:
4(3), P. 1073 - 1080
Published: March 1, 2024
Herein,
we
report
a
highly
regioselective
[4
+
2]-annulation
of
vinyl
sulfoxonium
ylides
with
ynoates
under
light-mediated
conditions.
The
reaction
proceeds
through
the
new
dienyl
ylide,
which
undergoes
photolysis
blue
light
irradiation
to
give
substituted
naphthalene
scaffolds.
method
presented
here
operates
at
room
temperature
and
does
not
require
addition
an
external
photosensitizer.
in
situ-generated
ylide
absorbs
acts
as
photosensitizer
for
formation
arenes.
synthetic
potential
these
benzannulations
was
further
illustrated
by
various
transformations
scale-up
reaction.
Moreover,
control
experiments
quantum
chemical
calculations
reveal
mechanistic
details
developed
Language: Английский
Stereoselective gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols via Metalloradical Catalysis
Srashti Bhardwaj,
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Dinesh Kumar Gopalakrishnan,
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Shalu Deshwal
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et al.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(4), P. 2805 - 2815
Published: Feb. 8, 2024
Multicomponent
reactions
that
involve
carbenes
with
nucleophiles
and
electrophiles
have
demonstrated
broad
applications
in
synthetic
chemistry.
However,
because
of
the
high
reactivity
transient
carbenes,
involving
two
carbene
precursors
nucleophile
presence
a
metal
catalyst
remain
unexplored.
Herein,
three-component
stereoselective
gem-difunctionalization
diazo
compounds
thiols
vinyl
sulfoxonium
ylide
is
disclosed
via
Co(II)-based
metalloradical
catalysis.
The
key
aspect
present
strategy
to
exploit
intrinsic
difference
ylides
thiol
catalysts.
Doyle–Kirmse
rearrangement
sulfonium
involves
convergent
assembly
situ-generated
intermediates,
such
as
allyl
sulfide
α-
metalloalkyl
radical
complex,
provide
expeditious
access
tertiary
scaffolds.
Combined
experimental
quantum
chemical
calculations
unveil
intricate
mechanism
this
reaction.
Furthermore,
theoretical
studies
on
noncovalent
interactions
selectivity-determining
transition
states
explain
origin
experimentally
obtained
diastereoselectivity.
Language: Английский
Divergent Approach to Highly Substituted Arenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Ynones
Daksh Singh Davas,
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Dinesh Kumar Gopalakrishnan,
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Krishnendu Bar
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et al.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(50), P. 8992 - 8996
Published: Dec. 12, 2023
Herein,
we
report
the
divergent
benzannulation
for
highly
substituted
arenes
using
vinyl
sulfoxonium
ylides
and
ynones.
The
addition
of
ynone
at
γ-position
leads
to
dienyl
ylide
that
can
undergo
selective
annulation
under
different
conditions
give
m-terphenyls
parabens.
Moreover,
control
experiments
quantum
chemical
calculations
reveal
two
distinct
reaction
mechanisms
both
annulations.
Language: Английский
Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides with diazo compounds and acetals
Dinesh Kumar Gopalakrishnan,
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Srashti Bhardwaj,
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Sandeep Kumar
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et al.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(28), P. 3846 - 3849
Published: Jan. 1, 2024
The
coupling
of
ylide-derived
carbene
with
diazo-derived
generated
dienoates
via
cascade
catalysis.
Similarly,
the
reaction
oxocarbenium
ion
afforded
alkylidenebutenolide
synergistic
Language: Английский
Divergent Access to α-Carbonyl-α′-vinyl Sulfoxonium Ylides and Polysubstituted Furans from β-Ketosulfoxonium Ylides and Ynone-Esters
Sudhir Rama Ingale,
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Manas Ranjan Sahu,
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Balasaheb R. Borade
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 28, 2025
Here,
we
describe
the
synthesis
of
novel
α-carbonyl-α'-vinyl
sulfoxonium
ylides
under
ambient,
catalyst-free,
and
additive-free
conditions,
demonstrating
broad
substrate
scope
scalability
using
β-ketosulfoxonium
α-ynone-esters.
Furthermore,
these
serve
as
versatile
intermediates
for
highly
substituted
furans
via
Brønsted
acid
(p-TsOH)
catalysis
at
130
°C.
This
approach
offers
key
advantages,
including
wide
compatibility,
divergent
product
formation
from
common
precursors,
gram-scale
feasibility,
good
to
excellent
yields.
Language: Английский
Regioselective Synthesis of N-Aryl Pyrazoles from Alkenyl Sulfoxonium Ylides and Aryl Diazonium Salts
Ramesh Kumar Vishwakarma,
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Raju Sen,
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Shalu Deshwal
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 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.
Language: Английский
Diastereoselective Cyclopropanation of α,β- Unsaturated Carbonyl Compounds with Vinyl Sulfoxonium Ylides
Shalu Deshwal,
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Dinesh Kumar Gopalakrishnan,
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Alok Purohit
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et al.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(31), P. 6294 - 6307
Published: Jan. 1, 2024
Vinyl
cyclopropane
scaffolds
were
synthesized
via
a
proline-catalysed
multicomponent
reaction
involving
vinyl
sulfoxonium
ylides,
aldehydes,
and
indane
1,3-dione.
Language: Английский
Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides
Siru Feng,
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Hailong Zhang,
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Jinhua Liu
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 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.
Language: Английский