β-(2-Alkynylphenyl)-α,β-ynones undergo a gold-catalyzed oxidative two-fold cyclization in the presence of N-oxides to give 1,3-disubstituted-8H-indeno[1,2-c]furan-8-ones in good yields. This cascade process is triggered by a selective oxygen transfer from an N-oxide onto the gold-activated alkynone to generate a α-dioxocarbene intermediate which, via carbene transfer across the remaining alkyne moiety and subsequent cyclization through nucleophilic attack by a carbonyl oxygen, achieves the construction of 1,3-disubstituted fused polycyclic furans. (Figure presented.).

Sequential Gold-Catalyzed Carbene Transfer/Ring Closure: Oxidative Cyclization of β-(2-Alkynylphenyl)-α,β-ynones to Indenofuranones

RODE, NAVNATH DNYANESHWAR;Marinelli, Fabio;Arcadi, Antonio;
2018-01-01

Abstract

β-(2-Alkynylphenyl)-α,β-ynones undergo a gold-catalyzed oxidative two-fold cyclization in the presence of N-oxides to give 1,3-disubstituted-8H-indeno[1,2-c]furan-8-ones in good yields. This cascade process is triggered by a selective oxygen transfer from an N-oxide onto the gold-activated alkynone to generate a α-dioxocarbene intermediate which, via carbene transfer across the remaining alkyne moiety and subsequent cyclization through nucleophilic attack by a carbonyl oxygen, achieves the construction of 1,3-disubstituted fused polycyclic furans. (Figure presented.).
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11697/133539
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