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905828

Sigma-Aldrich

Dimethylsulfoxonium-3-(chloro)benzoylmethylide

≥95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H11ClO2S
CAS Number:
2192257-03-5
Molecular Weight:
230.71
UNSPSC Code:
12352101

Assay

≥95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

125-129 °C

functional group

chloro
ketone
sulfoxide

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

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

905828-VAR:
905828-1G:
905828-BULK:
905828-5G:

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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.

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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