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Direct electrophilic fluorination of naproxen with NF-reagents. / Borodkin, Gennady I.; Elanov, Innokenty R.; Gatilov, Yury V. et al.

In: Journal of Fluorine Chemistry, Vol. 228, 109412, 01.12.2019.

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

Harvard

Borodkin, GI, Elanov, IR, Gatilov, YV & Shubin, VG 2019, 'Direct electrophilic fluorination of naproxen with NF-reagents', Journal of Fluorine Chemistry, vol. 228, 109412. https://doi.org/10.1016/j.jfluchem.2019.109412

APA

Borodkin, G. I., Elanov, I. R., Gatilov, Y. V., & Shubin, V. G. (2019). Direct electrophilic fluorination of naproxen with NF-reagents. Journal of Fluorine Chemistry, 228, [109412]. https://doi.org/10.1016/j.jfluchem.2019.109412

Vancouver

Borodkin GI, Elanov IR, Gatilov YV, Shubin VG. Direct electrophilic fluorination of naproxen with NF-reagents. Journal of Fluorine Chemistry. 2019 Dec 1;228:109412. doi: 10.1016/j.jfluchem.2019.109412

Author

Borodkin, Gennady I. ; Elanov, Innokenty R. ; Gatilov, Yury V. et al. / Direct electrophilic fluorination of naproxen with NF-reagents. In: Journal of Fluorine Chemistry. 2019 ; Vol. 228.

BibTeX

@article{11aca8ebb4dc4eb58cd36e3143e87652,
title = "Direct electrophilic fluorination of naproxen with NF-reagents",
abstract = "A novel effective protocol has been developed for direct fluorination of naproxen using the electrophilic fluorinating reagents 1-chloromethy1-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor{\texttrademark}, F-TEDA-BF4) and N-fluorobenzenesulfonimide (NFSI) in MeCN and H2O solvents with the formation of 2-(5-fluoro-6-methoxynaphthalen-2-yl)propionic and 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalen-2-yl)propionic acids. The reaction of naproxen with an excess of Selectfluor (mol. ratio NF-reagent/naproxen = 2.2) in MeOH gives methyl 2-(5,5-difluoro-6,6-dimethoxy-5,6-dihydronaphthalen-2-yl)propionate as the main product. The mechanistic aspects of the reactions and X-ray data of products are discussed.",
keywords = "Mechanism of fluorination, Naproxen, NF-reagent, X-ray analysis, DISCOVERY",
author = "Borodkin, {Gennady I.} and Elanov, {Innokenty R.} and Gatilov, {Yury V.} and Shubin, {Vyacheslav G.}",
year = "2019",
month = dec,
day = "1",
doi = "10.1016/j.jfluchem.2019.109412",
language = "English",
volume = "228",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Direct electrophilic fluorination of naproxen with NF-reagents

AU - Borodkin, Gennady I.

AU - Elanov, Innokenty R.

AU - Gatilov, Yury V.

AU - Shubin, Vyacheslav G.

PY - 2019/12/1

Y1 - 2019/12/1

N2 - A novel effective protocol has been developed for direct fluorination of naproxen using the electrophilic fluorinating reagents 1-chloromethy1-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™, F-TEDA-BF4) and N-fluorobenzenesulfonimide (NFSI) in MeCN and H2O solvents with the formation of 2-(5-fluoro-6-methoxynaphthalen-2-yl)propionic and 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalen-2-yl)propionic acids. The reaction of naproxen with an excess of Selectfluor (mol. ratio NF-reagent/naproxen = 2.2) in MeOH gives methyl 2-(5,5-difluoro-6,6-dimethoxy-5,6-dihydronaphthalen-2-yl)propionate as the main product. The mechanistic aspects of the reactions and X-ray data of products are discussed.

AB - A novel effective protocol has been developed for direct fluorination of naproxen using the electrophilic fluorinating reagents 1-chloromethy1-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™, F-TEDA-BF4) and N-fluorobenzenesulfonimide (NFSI) in MeCN and H2O solvents with the formation of 2-(5-fluoro-6-methoxynaphthalen-2-yl)propionic and 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalen-2-yl)propionic acids. The reaction of naproxen with an excess of Selectfluor (mol. ratio NF-reagent/naproxen = 2.2) in MeOH gives methyl 2-(5,5-difluoro-6,6-dimethoxy-5,6-dihydronaphthalen-2-yl)propionate as the main product. The mechanistic aspects of the reactions and X-ray data of products are discussed.

KW - Mechanism of fluorination

KW - Naproxen

KW - NF-reagent

KW - X-ray analysis

KW - DISCOVERY

UR - http://www.scopus.com/inward/record.url?scp=85075032229&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2019.109412

DO - 10.1016/j.jfluchem.2019.109412

M3 - Article

AN - SCOPUS:85075032229

VL - 228

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

M1 - 109412

ER -

ID: 22320428