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Documentos

905828

Sigma-Aldrich

Dimethylsulfoxonium-3-(chloro)benzoylmethylide

≥95%

Sinónimos:

1-(3-Chlorophenyl)-2-(dimethyl(oxo)-sulfaneylidene)ethan-1-one

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About This Item

Fórmula empírica (notación de Hill):
C10H11ClO2S
Número de CAS:
2192257-03-5
Peso molecular:
230.71
UNSPSC Code:
12352101

assay

≥95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

125-129 °C

storage temp.

−20°C

SMILES string

O=C(C1=CC=CC(Cl)=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

Rhodium-Catalyzed Relay Carbenoid Functionalization of Aromatic C-H Bonds toward Fused Heteroarenes

Related product

Referencia del producto
Descripción
Precios

905860

Dimethylsulfoxonium-4-(chloro)benzoylmethylide, ≥95%

905763

Dimethylsulfoxonium-4-(trifluoromethyl)benzoylmethylide, ≥95%

905771

Dimethylsulfoxonium-3-(methyl)benzoylmethylide, ≥95%

905798

Dimethylsulfoxonium-(isobutanoyl)methylide, ≥95%

905828

Dimethylsulfoxonium-3-(chloro)benzoylmethylide, ≥95%

905844

Dimethylsulfoxonium-4-(fluoro)benzoylmethylide, ≥95%

905704

Dimethylsulfoxonium-(N-Boc(4-piperidinecarbonoyl)methylide, ≥95%

905690

Dimethylsulfoxonium-2-(chloro)benzoylmethylide, ≥95%

905682

Dimethylsulfoxonium-3-(pyridoyl)methylide, ≥95%

905674

Dimethylsulfoxonium-2-(thiophenoyl)methylide, ≥95%

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Xiaopeng Wu et al.
Organic letters, 20(5), 1396-1399 (2018-02-23)
A rhodium-catalyzed annulation between ethyl benzimidates and α- aroyl sulfur ylides was developed, affording a series of pyrano[4,3,2-ij]isoquinoline derivatives in moderate to good yields with good functional group compatibility. The procedure featured dual ortho-C-H functionalization and dual cyclization in one
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.
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.

Contenido relacionado

Ketosulfoxonium Ylides

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

Ellman Group – Professor Product Portal

The Ellman group has participated in the development of a variety of C-H functionalization methods. An electron rich phosphine ligand has proven to be very useful for a variety of Rh(I)-catalyzed C-C bond forming reactions applicable to heterocycle synthesis as exemplified in the recent Science paper “Proton Donor Acidity Controls Selectivity in Nonaromatic Nitrogen Heterocycle Synthesis.” Another useful ligand developed for the highly functional group compatible direct arylation of nitrogen heterocycles is described in a 2008 J. Am. Chem. Soc. paper “Rh(I)-Catalyzed Arylation of Heterocycles via C-H Bond Activation: Expanded Scope through Mechanistic Insight.” The Ellman group also developed the chiral amine reagent tert-Butanesulfinamide, which is extensively used in academics and industry for the asymmetric synthesis of amines. A comprehensive survey of tert-Butanesulfinamide methods and applications up through 2009 is provided in the 2010 Chemical Reviews article, “Synthesis and Applications of tert-Butanesulfinamide.”

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