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905704

Sigma-Aldrich

Dimethylsulfoxonium-(N-Boc(4-piperidinecarbonoyl)methylide

≥95%

Synonyme(s) :

tert-Butyl 4-(2-(dimethyl(oxo)-sulfaneylidene)acetyl)piperidine-1-carboxylate

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About This Item

Formule empirique (notation de Hill):
C14H25NO4S
Numéro CAS:
2135471-18-8
Poids moléculaire :
303.42
Code UNSPSC :
12352005

Pureté

≥95%

Forme

solid

Capacité de réaction

reaction type: C-C Bond Formation

Pf

131-132 °C

Température de stockage

−20°C

Chaîne SMILES 

O=C(C1CCN(C(OC(C)(C)C)=O)CC1)C=S(C)(C)=O

Description générale

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.

Autres remarques

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

Rhodium(III)-catalyzed C−H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused[5,6]-bicyclic heterocycles

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Manuel Barday et al.
Angewandte Chemie (International ed. in English), 56(42), 13117-13121 (2017-08-31)
The functionalization of carbon-hydrogen bonds in non-nucleophilic substrates using α-carbonyl sulfoxonium ylides has not been so far investigated, despite the potential safety advantages that such reagents would provide over either diazo compounds or their in situ precursors. Described herein are
Gia L Hoang et al.
Tetrahedron, 74(26), 3318-3324 (2018-07-11)
The synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles via rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides is disclosed. Reactions proceeded in good to high yields for a range of aryl, heteroaryl and alkyl sulfoxonium ylides. In addition, 2-alkenyl imidazoles
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

Contenu apparenté

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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