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905798

Sigma-Aldrich

Dimethylsulfoxonium-(isobutanoyl)methylide

≥95%

Synonym(s):

1-(Dimethyl(oxo)-sulfaneylidene)-3-methylbutan-2-one

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About This Item

Empirical Formula (Hill Notation):
C7H14O2S
CAS Number:
1910095-11-2
Molecular Weight:
162.25
UNSPSC Code:
12352101

Assay

≥95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

140-144 °C

storage temp.

−20°C

SMILES string

O=C(C(C)C)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

Rhodium(III)-catalyzed C−H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused[5,6]-bicyclic heterocycles

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Alicia M Phelps et al.
The Journal of organic chemistry, 81(10), 4158-4169 (2016-04-23)
An iridium-catalyzed method was developed for the synthesis of imidazo-fused pyrrolopyrazines. The presence or absence of a nitrogenated ligand controlled the outcome of the reaction, leading to simple β-keto amine products in the absence of added ligand and the cyclized
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.

Related Content

Ketosulfoxonium Ylides

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

Ketosulfoxonium Ylides

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

Ketosulfoxonium Ylides

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

Ketosulfoxonium Ylides

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

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