NDLI: One molecule of ionic liquid and tert-alcohol on a polystyrene-support as catalysts for efficient nucleophilic substitution including fluorination.

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One molecule of ionic liquid and tert-alcohol on a polystyrene-support as catalysts for efficient nucleophilic substitution including fluorination.

Content Provider	Semantic Scholar
Author	Shinde, Sandip S. Patil, Sunil N.
Copyright Year	2014
Abstract	The tert-alcohol and ionic liquid solvents in one molecule [mim-(t)OH][OMs] was immobilized on polystyrene and reported to be a highly efficient catalyst in aliphatic nucleophilic substitution using alkali metal salts. Herein, we investigated the catalytic activity of a new structurally modified polymer-supported tert-alcohol functionalized imidazolium salt catalyst in nucleophilic substitution of 2-(3-methanesulfonyloxypropyoxy)naphthalene as a model substrate with various metal nucleophiles. The tert-alcohol moiety of the ionic liquid with a hexyl chain distance from polystyrene had a better catalytic activity compared to the other resin which lacked an alkyl linker and tert-alcohol moiety. We found that the maximum [mim-(t)OH][OMs] loading had the best catalytic efficacy among the tested polystyrene-based ionic liquids (PSILs) in nucleophilic fluorination. The catalytic efficiency of the PS[him-(t)OH][OMs] as a phase transfer catalyst (PTC) was determined by carrying out various nucleophilic substitutions using the corresponding alkali metal salts from the third to sixth periodic in CH3CN or tert-BuOH media. The scope of this protocol with primary and secondary polar substrates containing many heteroatoms is also reported. This PS[him-(t)OH][OMs] catalyst not only enhances the reactivity of alkali metal salts and reduces the formation of by-products but also affords high yield with easy isolation.
File Format	PDF HTM / HTML
DOI	10.1039/c4ob01781a
PubMed reference number	25302765
Journal	Medline
Volume Number	12
Issue Number	45
Alternate Webpage(s)	https://pubs.rsc.org/en/content/getauthorversionpdf/C4OB01781A
Alternate Webpage(s)	http://www.rsc.org/suppdata/ob/c4/c4ob01781a/c4ob01781a1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/c4ob01781a
Journal	Organic & biomolecular chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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