PPh3AuTFA Catalyzed in the Dearomatization
of 2‑Naphthols with Allenamides

An, Juzeng; Lombardi, Lorenzo; Grilli, Stefano; Bandini, Marco

doi:10.1021/acs.orglett.8b03018.s002

ol8b03018_si_002.pdf (3.45 MB)

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PPh₃AuTFA Catalyzed in the Dearomatization of 2‑Naphthols with Allenamides

journal contribution

posted on 2018-11-12, 12:50 authored by Juzeng An, Lorenzo Lombardi, Stefano Grilli, Marco Bandini

A new catalytic methodology for the direct dearomatization of substituted 2-naphthols via intermolecular condensation with allenamides is presented. PPh₃AuTFA (5 mol %) promotes the formal allylating dearomative protocol under mild conditions, large scope (24 examples), and high regioselectivity and stereoselectivity. The synergistic catalytic role played by the [PPh₃Au]⁺ (π-acid) and TFA^– (Lewis base) is highlighted.