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

Maiia I Aleksandrova; Stanislav V Lozovskiy; Steve Saulnier; Alexander A Golovanov; Irina A Boyarskaya; Aleksander V Vasilyev

doi:10.1039/c8ob01985a

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

Org Biomol Chem. 2018 Oct 31;16(42):7891-7902. doi: 10.1039/c8ob01985a.

Authors

Maiia I Aleksandrova¹, Stanislav V Lozovskiy, Steve Saulnier, Alexander A Golovanov, Irina A Boyarskaya, Aleksander V Vasilyev

Affiliation

¹ Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab. 7/9, Saint Petersburg, 199034, Russia.

PMID: 30306181
DOI: 10.1039/c8ob01985a

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.

Publication types

Research Support, Non-U.S. Gov't