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Hydroarylation of unsaturated carbon–carbon bonds in cross-conjugated enynones under the action of superacid CF3SO3H or acidic zeolite HUSY. Reaction mechanism and DFT study on cationic intermediate species

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Abstract

Reactions of cross-conjugated enynones,1,5-diarylpent-1-en-4-yn-3-ones, with arenes in the system TfOH-pyridine or under the action of acidic zeolite HUSY lead regioselectively to products of hydroarylation of the acetylene bond only,1,1,5-triarylpent-1,4-dien-3-ones, in yields up to 98%. These dienones add one more arene molecule to the double carbon–carbon bond in neat TfOH forming 1,1,5,5-tetraarylpent-1-en-3-ones in high yields. Cationic reaction intermediates have been studied by means of DFT calculations to elucidate plausible reaction mechanisms.

Graphical abstract: Hydroarylation of unsaturated carbon–carbon bonds in cross-conjugated enynones under the action of superacid CF3SO3H or acidic zeolite HUSY. Reaction mechanism and DFT study on cationic intermediate species

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Publication details

The article was received on 15 Aug 2018, accepted on 03 Oct 2018 and first published on 03 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB01985A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Hydroarylation of unsaturated carbon–carbon bonds in cross-conjugated enynones under the action of superacid CF3SO3H or acidic zeolite HUSY. Reaction mechanism and DFT study on cationic intermediate species

    M. I. Aleksandrova, S. V. Lozovskiy, S. Saulnier, A. A. Golovanov, I. A. Boyarskaya and A. V. Vasilyev, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01985A

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