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905704

Sigma-Aldrich

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

≥95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C14H25NO4S
CAS Number:
2135471-18-8
Molecular Weight:
303.42
UNSPSC Code:
12352005

Assay

≥95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

131-132 °C

functional group

ketone
sulfoxide

storage temp.

−20°C

SMILES string

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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

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

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