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Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps. / Lozovskiy, Stanislav V.; Vasilyev, Aleksander V.

в: Advanced Synthesis and Catalysis, Том 362, № 15, 04.08.2020, стр. 3121-3125.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Lozovskiy, SV & Vasilyev, AV 2020, 'Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps', Advanced Synthesis and Catalysis, Том. 362, № 15, стр. 3121-3125. https://doi.org/10.1002/adsc.202000534

APA

Lozovskiy, S. V., & Vasilyev, A. V. (2020). Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps. Advanced Synthesis and Catalysis, 362(15), 3121-3125. https://doi.org/10.1002/adsc.202000534

Vancouver

Lozovskiy SV, Vasilyev AV. Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps. Advanced Synthesis and Catalysis. 2020 Авг. 4;362(15):3121-3125. https://doi.org/10.1002/adsc.202000534

Author

Lozovskiy, Stanislav V. ; Vasilyev, Aleksander V. / Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps. в: Advanced Synthesis and Catalysis. 2020 ; Том 362, № 15. стр. 3121-3125.

BibTeX

@article{79f94e61b56a4fcbae2e47dd7d2fcc70,
title = "Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps",
abstract = "A two-step catalyst-free procedure for the construction of 3-perfluoroalkyl-2-(phosphoryl)methyl furans from commercially available 1-perfluoroalkyl 1,3-diketones is reported. Propargylic alcohols, prepared by direct alkynylation of the diketones, react with PCl3 via [2,3]-sigmatropic rearrangement – enolate cyclization sequence, leading to multifunctional furans. The reaction mechanism is supported by DFT study. In addition, the bioactivity modifying effect of phosphoryl group on 3-perfluoroalkyl furans is depicted. (Figure presented.).",
keywords = "Allenes, Furans, Catalyst-free, Perfluoroalkyl, PHARMACOLOGY, DISEASE, DRUGS, Allenes, Furans, SANDMEYER TRIFLUOROMETHYLATION, DISCOVERY",
author = "Lozovskiy, {Stanislav V.} and Vasilyev, {Aleksander V.}",
note = "Funding Information: This work was supported by Russian Scientific Foundation (grant no. 18‐13‐00008). Spectral studies were performed at Center for Magnetic Resonance, Center for Chemical Analysis and Materials Research of Saint Petersburg State University, Saint Petersburg, Russia. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",
year = "2020",
month = aug,
day = "4",
doi = "10.1002/adsc.202000534",
language = "English",
volume = "362",
pages = "3121--3125",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-Blackwell",
number = "15",

}

RIS

TY - JOUR

T1 - Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps

AU - Lozovskiy, Stanislav V.

AU - Vasilyev, Aleksander V.

N1 - Funding Information: This work was supported by Russian Scientific Foundation (grant no. 18‐13‐00008). Spectral studies were performed at Center for Magnetic Resonance, Center for Chemical Analysis and Materials Research of Saint Petersburg State University, Saint Petersburg, Russia. Publisher Copyright: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/8/4

Y1 - 2020/8/4

N2 - A two-step catalyst-free procedure for the construction of 3-perfluoroalkyl-2-(phosphoryl)methyl furans from commercially available 1-perfluoroalkyl 1,3-diketones is reported. Propargylic alcohols, prepared by direct alkynylation of the diketones, react with PCl3 via [2,3]-sigmatropic rearrangement – enolate cyclization sequence, leading to multifunctional furans. The reaction mechanism is supported by DFT study. In addition, the bioactivity modifying effect of phosphoryl group on 3-perfluoroalkyl furans is depicted. (Figure presented.).

AB - A two-step catalyst-free procedure for the construction of 3-perfluoroalkyl-2-(phosphoryl)methyl furans from commercially available 1-perfluoroalkyl 1,3-diketones is reported. Propargylic alcohols, prepared by direct alkynylation of the diketones, react with PCl3 via [2,3]-sigmatropic rearrangement – enolate cyclization sequence, leading to multifunctional furans. The reaction mechanism is supported by DFT study. In addition, the bioactivity modifying effect of phosphoryl group on 3-perfluoroalkyl furans is depicted. (Figure presented.).

KW - Allenes, Furans

KW - Catalyst-free

KW - Perfluoroalkyl

KW - PHARMACOLOGY

KW - DISEASE

KW - DRUGS

KW - Allenes

KW - Furans

KW - SANDMEYER TRIFLUOROMETHYLATION

KW - DISCOVERY

UR - http://www.scopus.com/inward/record.url?scp=85087204663&partnerID=8YFLogxK

U2 - 10.1002/adsc.202000534

DO - 10.1002/adsc.202000534

M3 - Article

AN - SCOPUS:85087204663

VL - 362

SP - 3121

EP - 3125

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 15

ER -

ID: 69889748