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Merck
CN

905828

Sigma-Aldrich

Dimethylsulfoxonium-3-(chloro)benzoylmethylide

≥95%

别名:

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

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About This Item

经验公式(希尔记法):
C10H11ClO2S
分子量:
230.71
UNSPSC代码:
12352101

方案

≥95%

表单

solid

反应适用性

reaction type: C-C Bond Formation

mp

125-129 °C

官能团

chloro
ketone
sulfoxide

储存温度

−20°C

SMILES字符串

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

一般描述

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.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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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.

相关内容

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

Ellman group developed electron-rich phosphine ligands for C-H functionalization and tert-Butanesulfinamide for asymmetric amine synthesis.

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