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905704

Sigma-Aldrich

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

≥95%

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C14H25NO4S
CAS-Nummer:
2135471-18-8
Molekulargewicht:
303.42
UNSPSC-Code:
12352005

Assay

≥95%

Form

solid

Eignung der Reaktion

reaction type: C-C Bond Formation

mp (Schmelzpunkt)

131-132 °C

Funktionelle Gruppe

ketone
sulfoxide

Lagertemp.

−20°C

SMILES String

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

Allgemeine Beschreibung

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.

Sonstige Hinweise

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

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Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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Lot/Batch Number

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Die Dokumentenbibliothek aufrufen

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

Verwandter Inhalt

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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