Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions

Hernández, José G.; Ardila-Fierro, Karen J.; Barišić, Dajana; Geneste, Hervé (2022) Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions. Beilstein journal of organic chemistry, 18 . pp. 182-189. ISSN 2195-951X

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Abstract

In the search for versatile reagents compatible with mechanochemical techniques, in this work we studied the reactivity of N- fluorobenzenesulfonimide (NFSI) by ball milling. We corroborated that, by mechanochemistry, NFSI can engage in a variety of reactions such as fluorinations, fluorodemethylations, sulfonylations, and amidations. In comparison to the protocols reported in solution, the mechanochemical reactions were accomplished in the absence of solvents, in short reaction times, and in yields comparable to or higher than their solvent-based counterparts.

Item Type:	Article
Uncontrolled Keywords:	amidation ; ball mill ; fluorination ; in situ monitoring ; mechanochemistry ; NFSI ; Raman monitoring ; sulfonylation
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Physical Chemistry
Projects:	Project title Project leader Project code Project type Mehanokemijska aktivacija i funkcionalizacija veze C–H potaknuta paladijem i usmjerena ligandom Ćurić, Manda IP-2019-04-9951 HRZZ
Depositing User:	Sofija Konjević
Date Deposited:	23 Feb 2022 10:05
URI:	http://fulir.irb.hr/id/eprint/7017
DOI:	10.3762/bjoc.18.20

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