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Synthesis of gold allyloxysulfonium complexes and elimination to form an α,β-unsaturated aldehyde

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Abstract

Treatment of the gold vinyl carbene/allylic cation complex (E)-[(IPr)AuC(H)C(H)C(4-C6H4OMe)2]+ OTf with sulfoxides at −95 °C formed the corresponding gold allyloxysulfonium complexes [(IPr)AuC(H)(OSR2)C(H)[double bond, length as m-dash]C(4-C6H4OMe)2]+ OTf [R = Me, –(CH2)4–, Ar] in ≥95 ± 5% NMR yield. Allyloxysulfonium gold complexes underwent elimination at or below room temperature to form 3,3-bis(4-methoxyphenyl)acrylaldehyde in ≥67% yield.

Graphical abstract: Synthesis of gold allyloxysulfonium complexes and elimination to form an α,β-unsaturated aldehyde

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Publication details

The article was received on 24 Aug 2019, accepted on 17 Oct 2019 and first published on 21 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC06589J
Chem. Commun., 2019, Advance Article

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    Synthesis of gold allyloxysulfonium complexes and elimination to form an α,β-unsaturated aldehyde

    N. Kim and R. A. Widenhoefer, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC06589J

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