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905674

Sigma-Aldrich

Dimethylsulfoxonium-2-(thiophenoyl)methylide

≥95%

Synonym(s):

2-(Dimethyl(oxo)-sulfaneylidene)-1-(thiophen-2-yl)ethan-1-one

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About This Item

Empirical Formula (Hill Notation):
C8H10O2S2
CAS Number:
1910095-20-3
Molecular Weight:
202.29
UNSPSC Code:
12352005

Assay

≥95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

187-189 °C

storage temp.

−20°C

SMILES string

O=C(C1=CC=CS1)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

Ligand-Controlled Synthesis of Azoles via Ir-Catalyzed Reactions of Sulfoxonium Ylides with 2-Amino Heterocycles

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Alicia M Phelps et al.
The Journal of organic chemistry, 81(10), 4158-4169 (2016-04-23)
An iridium-catalyzed method was developed for the synthesis of imidazo-fused pyrrolopyrazines. The presence or absence of a nitrogenated ligand controlled the outcome of the reaction, leading to simple β-keto amine products in the absence of added ligand and the cyclized
Kim Søholm Halskov et al.
Organic letters, 20(8), 2464-2467 (2018-03-28)
Azolopyrimidines are efficiently prepared by direct imidoyl C-H bond activation. Annulations of N-azolo imines with sulfoxonium ylides and diazoketones under redox-neutral conditions and alkynes under oxidizing conditions provide products with various arrangements of nitrogen atoms and carbon substituents. We have
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
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

Related Content

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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