Mechanochemical Fluorination of Naproxen and Its Salts with F–TEDA–BF4

Mechanochemical Fluorination of Naproxen and Its Salts with F–TEDA–BF4 Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2023, Volume: 59, Number: 11, Pages: 1858-1866 Pages count : 9 DOI: 10.1134/s1070428023110039

Tags

N–F reagent naproxen naproxen salts mechanochemical fluorination

Authors

Borodkin G.I. ¹ , Elanov I.R. ¹ , Shubin V.G. ¹

Affiliations

1	Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences

The mechanochemical fluorination of naproxen and its salts (Li, Na, and K) with 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor, F–TEDA–BF4) was studied. The reaction of naproxen with an excess of Selectfluor gives 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalen-2-yl)propionic acid in high yield. Small additives of Al2O3, SiO2, M2CO3 (M = Na, K, Rb, Cs), ionic liquids (ILs), crown ethers, and N-bases accelerate the reaction of naproxen with Selectfluor and increases the monofluorination/difluorination product ratio.

Borodkin G.I. , Elanov I.R. , Shubin V.G.
Mechanochemical Fluorination of Naproxen and Its Salts with F–TEDA–BF4
Russian Journal of Organic Chemistry. 2023. V.59. N11. P.1858-1866. DOI: 10.1134/s1070428023110039 WOS РИНЦ

Бородкин Г.И. , Еланов И.Р. , Шубин В.Г.
Механохимическое фторирование напроксена и его солей реагентом F-TEDA-BF4
Журнал органической химии (RUSS J ORG CHEM+). 2023. Т.59. №11. С.1418-1426. DOI: 10.31857/S0514749223110034 РИНЦ

Submitted:	Aug 22, 2022
Accepted:	Aug 29, 2022
Published online:	Feb 5, 2024

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