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905763

Sigma-Aldrich

Dimethylsulfoxonium-4-(trifluoromethyl)benzoylmethylide

≥95%

Synonym(s):

2-(Dimethyl(oxo)-sulfaneylidene)-1-(4-(trifluoromethyl)phenyl)ethan-1-one

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About This Item

Empirical Formula (Hill Notation):
C11H11F3O2S
CAS Number:
2118974-83-5
Molecular Weight:
264.26
UNSPSC Code:
12352101

Assay

≥95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

158 °C

storage temp.

−20°C

SMILES string

O=C(C1=CC=C(C(F)(F)F)C=C1)C=S(C)(C)=O

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
Kim Søholm Halskov et al.
Organic letters, 20(8), 2464-2467 (2018-03-28)
Azolopyrimidines are efficiently prepared by direct imidoyl C-H bond activation. Annulations of N-azolo imines with sulfoxonium ylides and diazoketones under redox-neutral conditions and alkynes under oxidizing conditions provide products with various arrangements of nitrogen atoms and carbon substituents. We have
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
Panjie Hu et al.
Organic letters, 20(8), 2160-2163 (2018-04-03)
Rh(III)-catalyzed cascade C-H activation of benzoylacetonitriles and annulation with sulfoxonium ylides was realized, leading to selective synthesis of naphthols, 2,3-dihydronaphtho[1,8- bc]pyrans, and naphtho[1,8- bc]pyrans. This step-economic reaction proceeded efficiently under mild and redox-neutral conditions via multiple C-H activations.
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