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905828

Sigma-Aldrich

Dimethylsulfoxonium-3-(chloro)benzoylmethylide

≥95%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C10H11ClO2S
Numero CAS:
2192257-03-5
Peso molecolare:
230.71
Codice UNSPSC:
12352101

Saggio

≥95%

Stato

solid

Impiego in reazioni chimiche

reaction type: C-C Bond Formation

Punto di fusione

125-129 °C

Gruppo funzionale

chloro
ketone
sulfoxide

Temperatura di conservazione

−20°C

Stringa SMILE

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

Descrizione generale

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.

Altre note

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

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

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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%

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

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

905674

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Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°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.

Contenuto correlato

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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