Gold-Catalysed Heck Reaction: Fact or Fiction?

Peter H. M. Budzelaar, Manfred Bochmann, Martina Landrini, Luca Rocchigiani

Research output: Working paperPreprint

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Abstract

Two recent high-profile publications described the formation of Heck-type arylated alkenes catalysed by MeDalPhosAuCl / AgOTf (J. Am. Chem. Soc. 2023, 145, 8810) and their cyclisation to tetralines (Angew. Chem. Int. Ed. 2023, e202312786), claiming that these were the first demonstrations of alkene insertion into Au-aryl bonds, β-H elimination and chain-walking by Au-H cations under catalytic conditions. We show here that in fact this chemistry is a two-stage process. Only the first step, the production of an alkyl triflate ester as primary product by the well-known alkene heteroarylation sequence, involves gold. The subsequent formation of Heck-type olefins and their cyclisation to tetralines represent are classical H+-triggered carbocationic chemistry. These steps proceed in the absence of gold with identical results. Literature claims of new gold reactivity such as chain walking by the putative [LAuH]2+ dication have no basis in fact.
Original languageEnglish
PublisherChemRxiv
DOIs
Publication statusPublished - 10 Jan 2024

Keywords

  • Gold complexes
  • catalysis
  • Mechanisms
  • Heck reaction

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