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Merck
CN

905860

Sigma-Aldrich

Dimethylsulfoxonium-4-(chloro)benzoylmethylide

≥95%

别名:

1-(4-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

154 °C

储存温度

−20°C

SMILES字符串

O=C(C1=CC=C(Cl)C=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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分析证书(COA)

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Alexánder Garay Talero et al.
Organic letters, 20(22), 7206-7211 (2018-10-27)
A general, mild, and versatile synthesis of the challenging α-aryl-β-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible β-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a
Youwei Xu et al.
Organic letters, 19(16), 4307-4310 (2017-08-08)
Direct and efficient synthesis of 1-naphthols has been realized via Rh(III)-catalyzed C-H activation of sulfoxonium ylides and subsequent annulation with alkynes, where the sulfoxonium ylide functioned as a new traceless bifunctional directing group. This reaction occurred under redox-neutral conditions with
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.

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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