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. 2019 Jul 17;25(40):9385-9389.
doi: 10.1002/chem.201900996. Epub 2019 Apr 17.

Gold-Catalyzed Cyclisation by 1,4-Dioxidation

Vanessa Claus  1 , Lise Molinari  1 , Simon Büllmann  1 , Jean Thusek  1 , Matthias Rudolph  1 , Frank Rominger  1 , A Stephen K Hashmi  1   2
Affiliations

Gold-Catalyzed Cyclisation by 1,4-Dioxidation

Vanessa Claus et al. Chemistry. .

Abstract

Amide-substituted diynes were cyclized in the presence of a cationic gold catalyst and an external nucleophile leading to 1-indenones and 1-iminoindenones. The electron-donating features of the nitrogen atom enable the formation of a reactive ketene iminium ion, which can be trapped by either diphenyl sulfoxide or anthranil as nucleophiles in a subsequent oxidation step, providing substituted inden-1-on-3-carboxamides.

Keywords: cyclization; diphenylsulfoxide; diynes; gold; ynamides.

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