Research output: Contribution to journal › Article › peer-review
Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps. / Lozovskiy, Stanislav V.; Vasilyev, Aleksander V.
In: Advanced Synthesis and Catalysis, Vol. 362, No. 15, 04.08.2020, p. 3121-3125.Research output: Contribution to journal › Article › peer-review
}
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