Reactivity of “Ligand-Free” Au+: C–H and C–C Activation versus π Coordination

Nicky Savjani, Sean P. Bew, David L. Hughes, Simon J. Lancaster, Manfred Bochmann

Research output: Contribution to journalArticlepeer-review

Abstract

[(Me2S)Au]+ cations, generated from (Me2S)AuCl and AgSbF6 in dichloromethane at 0–20 °C, serve as sources of solvated Au+ (alongside unreactive [Au(SMe2)2]+), which reacts with the methyl-substituted arenes C6Me6–nHn (n = 0–2) with C–H bond cleavage to give the sulfonium salts [C6Me5–nHnCH2SMe2]+. There was no evidence for arene π coordination to Au+ or for the formation of σ-bonded Au–benzyl species. Surprisingly, the reaction of Au+ with CH2Ar2 leads to C–C bond cleavage (Ar = 2,4,6-C6H2Me3). The reactions are highly selective for benzylic C–H and C–C bonds, whereas metalation of the arene ring is not observed.
Original languageEnglish
Pages (from-to)2534-2537
Number of pages4
JournalOrganometallics
Volume31
Issue number7
DOIs
Publication statusPublished - 2 Dec 2011

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