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