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Merck
CN

905844

Dimethylsulfoxonium-4-(fluoro)benzoylmethylide

≥95%

Synonym(s):

2-(Dimethyl(oxo)-sulfaneylidene)-1-(4-fluorophenyl)ethan-1-one

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About This Item

Empirical Formula (Hill Notation):
C10H11FO2S
CAS Number:
2118974-82-4
Molecular Weight:
214.26
UNSPSC Code:
12352101

Key Documents

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Assay

≥95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

112-116 °C

storage temp.

−20°C

General description

Sulfoxonium ylides are highly stable carbene precursors, serving as a safer alternative to diazo compounds as they that do not generate gases as byproducts. Sulfoxonium ylides have been shown to be effective in a wide array of transition metal catalyzed C-H functionalization and coupling reactions.

Other Notes

For additional technical information see Ketosulfoxonium Ylides: Safe, Versatile Carbene Equivalents

Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Prochiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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30362356
PubMed ID (for auto-filling citation data) null
Adaptation in health behavior: modern and traditional medicine in a West Mexican community.
C McClain
Social science & medicine, 11(5), 341-347 (1977-03-01)
Alexánder Garay Talero et al.
Organic letters, 20(22), 7206-7211 (2018-10-27)
A general, mild, and versatile synthesis of the challenging α-aryl-β-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible β-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a
James D Neuhaus et al.
Angewandte Chemie (International ed. in English), 57(49), 16215-16218 (2018-09-29)
A ruthenium-catalysed cross-olefination of diazo compounds and sulfoxonium ylides is presented. Our reaction design exploits the intrinsic difference in reactivity of diazo compounds and sulfoxonium ylides as both carbene precursors and nucleophiles, which results in a highly selective reaction.
Shuying Ji et al.
Organic letters, 20(18), 5981-5984 (2018-09-13)
A Cp*Co(III)-catalyzed C-H bond functionalization of a range of arenes by employing sulfoxonium ylides as carbene precursors instead of diazo compounds and other carbene precursors has been established. This reaction is highly efficient without any additive, possesses high step and
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Related Content

Ketosulfoxonium Ylides

Ketosulfoxonium ylides serve as versatile carbene equivalents for large-scale reactions, releasing dimethyl sulfoxide biproducts.

Ellman Group – Professor Product Portal

Ellman group developed electron-rich phosphine ligands for C-H functionalization and tert-Butanesulfinamide for asymmetric amine synthesis.

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