Hydroarylation of unsaturated carbon-carbon bonds in cross-conjugated enynones under the action of superacid CF 3 SO 3 H or acidic zeolite HUSY. Reaction mechanism and DFT study on cationic intermediate species

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Hydroarylation of unsaturated carbon-carbon bonds in cross-conjugated enynones under the action of superacid CF ₃ SO ₃ H or acidic zeolite HUSY. Reaction mechanism and DFT study on cationic intermediate species. / Aleksandrova, Maiia I.; Lozovskiy, Stanislav V.; Saulnier, Steve; Golovanov, Alexander A.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 42, 2018, p. 7891-7902.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{aad2a9e916534b7fae098527d56f7e95,

title = "Hydroarylation of unsaturated carbon-carbon bonds in cross-conjugated enynones under the action of superacid CF 3 SO 3 H or acidic zeolite HUSY. Reaction mechanism and DFT study on cationic intermediate species",

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.",

keywords = "ACCESS, ELECTROPHILICITY INDEX, KETONES",

author = "Aleksandrova, {Maiia I.} and Lozovskiy, {Stanislav V.} and Steve Saulnier and Golovanov, {Alexander A.} and Boyarskaya, {Irina A.} and Vasilyev, {Aleksander V.}",

note = "Funding Information: This work was supported by the Russian Scientific Foundation (grant no. 18-13-00008). Spectral studies were performed at the Center for Magnetic Resonance, Center for Chemical Analysis and Materials Research and Research Center for X-ray Diffraction Studies of Saint Petersburg State University, Saint Petersburg, Russia. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",

year = "2018",

doi = "10.1039/c8ob01985a",

language = "English",

volume = "16",

pages = "7891--7902",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "42",

}

RIS

TY - JOUR

T1 - Hydroarylation of unsaturated carbon-carbon bonds in cross-conjugated enynones under the action of superacid CF 3 SO 3 H or acidic zeolite HUSY. Reaction mechanism and DFT study on cationic intermediate species

AU - Aleksandrova, Maiia I.

AU - Lozovskiy, Stanislav V.

AU - Saulnier, Steve

AU - Golovanov, Alexander A.

AU - Boyarskaya, Irina A.

AU - Vasilyev, Aleksander V.

N1 - Funding Information: This work was supported by the Russian Scientific Foundation (grant no. 18-13-00008). Spectral studies were performed at the Center for Magnetic Resonance, Center for Chemical Analysis and Materials Research and Research Center for X-ray Diffraction Studies of Saint Petersburg State University, Saint Petersburg, Russia. Publisher Copyright: © The Royal Society of Chemistry. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

KW - ACCESS

KW - ELECTROPHILICITY INDEX

KW - KETONES

UR - http://www.scopus.com/inward/record.url?scp=85055650108&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/hydroarylation-unsaturated-carboncarbon-bonds-crossconjugated-enynones-under-action-superacid-cf3so3

U2 - 10.1039/c8ob01985a

DO - 10.1039/c8ob01985a

M3 - Article

C2 - 30306181

AN - SCOPUS:85055650108

VL - 16

SP - 7891

EP - 7902

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 42

ER -

ID: 35536541