Facile nucleophilic fluorination by synergistic effect between polymer-supported ionic liquid catalyst and tert-alcohol reaction media system

Dong Wook Kim; Hwan Jeong Jeong; Seok Tae Lim; Myung Hee Sohn; Dae Yoon Chi

doi:10.1016/j.tet.2008.02.094

Facile nucleophilic fluorination by synergistic effect between polymer-supported ionic liquid catalyst and tert-alcohol reaction media system

Dong Wook Kim, Hwan Jeong Jeong, Seok Tae Lim, Myung Hee Sohn, Dae Yoon Chi

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

44 Scopus citations

Abstract

A highly efficient method was developed for nucleophilic fluorination using an alkali metal fluoride through the synergistic effect of the polymer-supported ionic liquid (PSIL) as a catalyst and tert-alcohol as an alternative reaction media. This PSIL/tert-alcohol system not only enhances the reactivity of alkali metal fluorides and reduces the formation of by-products but also allows the use of a polymer-supported catalyst protocol. As an example, the nucleophilic fluorinations of the model compound, 2-(3-bromopropoxy)naphthalene, with CsF using only tert-amyl alcohol as solvent (for 2 h reaction time), 0.5 equiv of PS[hmim][BF₄] in CH₃CN (for 12 h reaction time), and 0.5 equiv of PS[hmim][BF₄] in tert-amyl alcohol (which is a PSIL/tert-alcohol system for the synergistic effect; for 2 h reaction time) provided 18, 40, and 84% yield, respectively. The characteristics of the nucleophilic fluorination reactions of some halo- and alkanesulfonyloxyalkane systems to the corresponding fluoroalkanes using various alkali metal fluorides are also reported.

Original language	English
Pages (from-to)	4209-4214
Number of pages	6
Journal	Tetrahedron
Volume	64
Issue number	19
DOIs	https://doi.org/10.1016/j.tet.2008.02.094
State	Published - 5 May 2008
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by the fund of Chonbuk National University Hospital Research Institute of Clinical Medicine (to D.W.K.), grant from the Atomic Energy Technology and Development Program of KOSEF (2008-00285 to D.W.K), and KOSEF grant funded by the Korea government (MOST, 2006-03770 to D.Y.C.).

Keywords

Alkali metal fluoride
Fluorination
Ionic liquid
Nucleophilic substitution
Polymer-supported ionic liquid
tert-Alcohol

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10.1016/j.tet.2008.02.094

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title = "Facile nucleophilic fluorination by synergistic effect between polymer-supported ionic liquid catalyst and tert-alcohol reaction media system",

abstract = "A highly efficient method was developed for nucleophilic fluorination using an alkali metal fluoride through the synergistic effect of the polymer-supported ionic liquid (PSIL) as a catalyst and tert-alcohol as an alternative reaction media. This PSIL/tert-alcohol system not only enhances the reactivity of alkali metal fluorides and reduces the formation of by-products but also allows the use of a polymer-supported catalyst protocol. As an example, the nucleophilic fluorinations of the model compound, 2-(3-bromopropoxy)naphthalene, with CsF using only tert-amyl alcohol as solvent (for 2 h reaction time), 0.5 equiv of PS[hmim][BF4] in CH3CN (for 12 h reaction time), and 0.5 equiv of PS[hmim][BF4] in tert-amyl alcohol (which is a PSIL/tert-alcohol system for the synergistic effect; for 2 h reaction time) provided 18, 40, and 84% yield, respectively. The characteristics of the nucleophilic fluorination reactions of some halo- and alkanesulfonyloxyalkane systems to the corresponding fluoroalkanes using various alkali metal fluorides are also reported.",

keywords = "Alkali metal fluoride, Fluorination, Ionic liquid, Nucleophilic substitution, Polymer-supported ionic liquid, tert-Alcohol",

author = "Kim, {Dong Wook} and Jeong, {Hwan Jeong} and Lim, {Seok Tae} and Sohn, {Myung Hee} and Chi, {Dae Yoon}",

note = "Funding Information: This work was supported by the fund of Chonbuk National University Hospital Research Institute of Clinical Medicine (to D.W.K.), grant from the Atomic Energy Technology and Development Program of KOSEF (2008-00285 to D.W.K), and KOSEF grant funded by the Korea government (MOST, 2006-03770 to D.Y.C.). ",

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AU - Kim, Dong Wook

AU - Jeong, Hwan Jeong

AU - Lim, Seok Tae

AU - Sohn, Myung Hee

AU - Chi, Dae Yoon

N1 - Funding Information: This work was supported by the fund of Chonbuk National University Hospital Research Institute of Clinical Medicine (to D.W.K.), grant from the Atomic Energy Technology and Development Program of KOSEF (2008-00285 to D.W.K), and KOSEF grant funded by the Korea government (MOST, 2006-03770 to D.Y.C.).

PY - 2008/5/5

Y1 - 2008/5/5

N2 - A highly efficient method was developed for nucleophilic fluorination using an alkali metal fluoride through the synergistic effect of the polymer-supported ionic liquid (PSIL) as a catalyst and tert-alcohol as an alternative reaction media. This PSIL/tert-alcohol system not only enhances the reactivity of alkali metal fluorides and reduces the formation of by-products but also allows the use of a polymer-supported catalyst protocol. As an example, the nucleophilic fluorinations of the model compound, 2-(3-bromopropoxy)naphthalene, with CsF using only tert-amyl alcohol as solvent (for 2 h reaction time), 0.5 equiv of PS[hmim][BF4] in CH3CN (for 12 h reaction time), and 0.5 equiv of PS[hmim][BF4] in tert-amyl alcohol (which is a PSIL/tert-alcohol system for the synergistic effect; for 2 h reaction time) provided 18, 40, and 84% yield, respectively. The characteristics of the nucleophilic fluorination reactions of some halo- and alkanesulfonyloxyalkane systems to the corresponding fluoroalkanes using various alkali metal fluorides are also reported.

AB - A highly efficient method was developed for nucleophilic fluorination using an alkali metal fluoride through the synergistic effect of the polymer-supported ionic liquid (PSIL) as a catalyst and tert-alcohol as an alternative reaction media. This PSIL/tert-alcohol system not only enhances the reactivity of alkali metal fluorides and reduces the formation of by-products but also allows the use of a polymer-supported catalyst protocol. As an example, the nucleophilic fluorinations of the model compound, 2-(3-bromopropoxy)naphthalene, with CsF using only tert-amyl alcohol as solvent (for 2 h reaction time), 0.5 equiv of PS[hmim][BF4] in CH3CN (for 12 h reaction time), and 0.5 equiv of PS[hmim][BF4] in tert-amyl alcohol (which is a PSIL/tert-alcohol system for the synergistic effect; for 2 h reaction time) provided 18, 40, and 84% yield, respectively. The characteristics of the nucleophilic fluorination reactions of some halo- and alkanesulfonyloxyalkane systems to the corresponding fluoroalkanes using various alkali metal fluorides are also reported.

KW - Alkali metal fluoride

KW - Fluorination

KW - Ionic liquid

KW - Nucleophilic substitution

KW - Polymer-supported ionic liquid

KW - tert-Alcohol

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JO - Tetrahedron

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Facile nucleophilic fluorination by synergistic effect between polymer-supported ionic liquid catalyst and tert-alcohol reaction media system

Abstract

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Keywords

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