Polyfluorinated quaternary ammonium salts of polyoxometalate anions: Fluorous biphasic oxidation catalysis with and without fluorous solvents

Galia Maayan; Richard H. Fish; Ronny Neumann

doi:10.1021/ol0348598

Polyfluorinated quaternary ammonium salts of polyoxometalate anions: Fluorous biphasic oxidation catalysis with and without fluorous solvents

Galia Maayan, Richard H. Fish, Ronny Neumann^*

^*Corresponding author for this work

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

74 Scopus citations

Abstract

[Matrix presented] Polyfluorinated quaternary ammonium cations, [CF ₃(CF₂)₇(CH₂)₃] ₃CH₃N⁺ (R_FN⁺), were synthesized and used as countercations for the [WZnM₂(H ₂O)₂(ZnW₉O₃₄)₂] ^12- (M = Mn(II), Zn(II)) polyoxometalate. The (R_FN ⁺)₁₂[WZnM₂(H₂0)₂ (ZnW₉O₃₄)₂] compounds were fluorous biphasic catalysts for alcohol and alkenol oxidation, and alkene epoxidation with aqueous hydrogen peroxide. Reaction protocols with or without a fluorous solvent were tested. The catalytic activity and selectivity was affected by both the hydrophobicity of the solvent and the substrate.

Original language	English
Pages (from-to)	3547-3550
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	20
DOIs	https://doi.org/10.1021/ol0348598
State	Published - 2 Oct 2003
Externally published	Yes

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title = "Polyfluorinated quaternary ammonium salts of polyoxometalate anions: Fluorous biphasic oxidation catalysis with and without fluorous solvents",

abstract = "[Matrix presented] Polyfluorinated quaternary ammonium cations, [CF 3(CF2)7(CH2)3] 3CH3N+ (RFN+), were synthesized and used as countercations for the [WZnM2(H 2O)2(ZnW9O34)2] 12- (M = Mn(II), Zn(II)) polyoxometalate. The (RFN +)12[WZnM2(H20)2 (ZnW9O34)2] compounds were fluorous biphasic catalysts for alcohol and alkenol oxidation, and alkene epoxidation with aqueous hydrogen peroxide. Reaction protocols with or without a fluorous solvent were tested. The catalytic activity and selectivity was affected by both the hydrophobicity of the solvent and the substrate.",

author = "Galia Maayan and Fish, {Richard H.} and Ronny Neumann",

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doi = "10.1021/ol0348598",

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T1 - Polyfluorinated quaternary ammonium salts of polyoxometalate anions

T2 - Fluorous biphasic oxidation catalysis with and without fluorous solvents

AU - Maayan, Galia

AU - Fish, Richard H.

AU - Neumann, Ronny

PY - 2003/10/2

Y1 - 2003/10/2

N2 - [Matrix presented] Polyfluorinated quaternary ammonium cations, [CF 3(CF2)7(CH2)3] 3CH3N+ (RFN+), were synthesized and used as countercations for the [WZnM2(H 2O)2(ZnW9O34)2] 12- (M = Mn(II), Zn(II)) polyoxometalate. The (RFN +)12[WZnM2(H20)2 (ZnW9O34)2] compounds were fluorous biphasic catalysts for alcohol and alkenol oxidation, and alkene epoxidation with aqueous hydrogen peroxide. Reaction protocols with or without a fluorous solvent were tested. The catalytic activity and selectivity was affected by both the hydrophobicity of the solvent and the substrate.

AB - [Matrix presented] Polyfluorinated quaternary ammonium cations, [CF 3(CF2)7(CH2)3] 3CH3N+ (RFN+), were synthesized and used as countercations for the [WZnM2(H 2O)2(ZnW9O34)2] 12- (M = Mn(II), Zn(II)) polyoxometalate. The (RFN +)12[WZnM2(H20)2 (ZnW9O34)2] compounds were fluorous biphasic catalysts for alcohol and alkenol oxidation, and alkene epoxidation with aqueous hydrogen peroxide. Reaction protocols with or without a fluorous solvent were tested. The catalytic activity and selectivity was affected by both the hydrophobicity of the solvent and the substrate.

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Polyfluorinated quaternary ammonium salts of polyoxometalate anions: Fluorous biphasic oxidation catalysis with and without fluorous solvents

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