Direct electrophilic fluorination of naproxen with NF-reagents

Direct electrophilic fluorination of naproxen with NF-reagents Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2019, Volume: 228, Article number : UNSP 109412, Pages count : DOI: 10.1016/j.jfluchem.2019.109412

Tags

NF-reagent; Naproxen; Mechanism of fluorination; X-ray analysis

Authors

Borodkin Gennady I. ^1,2 , Elanov Innokenty R. ¹ , Gatilov Yury V. ¹ , Shubin Vyacheslav G. ¹

Affiliations

1	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Acad Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogov St, Novosibirsk 630090, Russia

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 (TM), 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.

Borodkin G.I. , Elanov I.R. , Gatilov Y.V. , Shubin V.G.
Direct electrophilic fluorination of naproxen with NF-reagents
Journal of Fluorine Chemistry. 2019. V.228. UNSP 109412 . DOI: 10.1016/j.jfluchem.2019.109412 WOS Scopus РИНЦ

Published print:

Dec 1, 2019

Web of science	WOS:000501399400010
Scopus	2-s2.0-85075032229
Elibrary	41712472
OpenAlex	W2989532354