Room-temperature nucleophilic aromatic fluorination: Experimental and theoretical studies

Haoran Sun; Stephen G. DiMagno

doi:10.1002/anie.200504555

Room-temperature nucleophilic aromatic fluorination: Experimental and theoretical studies

Haoran Sun, Stephen G. DiMagno

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

180 Scopus citations

Abstract

(Chemical Equation Presented) Taming the reagent: The use of anhydrous tetrabutylammonium fluoride (TBAF_anh) in nucleophilic aromatic substitution reactions, including variants of the selective halogen-exchange and fluorodenitration processes (see scheme), was investigated. It was shown that TBAF_anh permits these reactions to be performed under surprisingly mild conditions if it is used in relatively nonpolar media.

Original language	English (US)
Pages (from-to)	2720-2725
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	17
DOIs	https://doi.org/10.1002/anie.200504555
State	Published - Apr 21 2006
Externally published	Yes

Keywords

Density functional calculations
Fluorine nucleophilic aromatic substitution
Synthetic methods
Tetrabutylammonium fluoride

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200504555

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AB - (Chemical Equation Presented) Taming the reagent: The use of anhydrous tetrabutylammonium fluoride (TBAFanh) in nucleophilic aromatic substitution reactions, including variants of the selective halogen-exchange and fluorodenitration processes (see scheme), was investigated. It was shown that TBAFanh permits these reactions to be performed under surprisingly mild conditions if it is used in relatively nonpolar media.

KW - Density functional calculations

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KW - Synthetic methods

KW - Tetrabutylammonium fluoride

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Room-temperature nucleophilic aromatic fluorination: Experimental and theoretical studies

Abstract

Keywords

ASJC Scopus subject areas

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