Silica-supported chlorometallate(III) ionic liquids as recyclable catalysts for Diels–Alder reaction under solventless conditions

Karolina Matuszek; Anna Chrobok; Piotr Latos; Magdalena Markiton; Katarzyna Szymanska; Andrzej  Jarzebski; Malgorzata Swadzba-Kwasny

doi:10.1039/C6CY01771A

Silica-supported chlorometallate(III) ionic liquids as recyclable catalysts for Diels–Alder reaction under solventless conditions

Karolina Matuszek, Anna Chrobok, Piotr Latos, Magdalena Markiton, Katarzyna Szymanska, Andrzej Jarzebski, Malgorzata Swadzba-Kwasny

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Abstract

A range of Lewis acidic metal chlorides were tested as homogeneous catalysts in a model Diels–Alder reaction; AlCl3 and GaCl3 performed best in terms of conversion and endo : exo selectivity. Based on this outcome, the corresponding chlorometallate(III) ionic liquids were tested as homogeneous catalysts, without a decrease in performance compared to the chlorides. Finally, these ionic liquids were heterogenised by covalent tethering of the cation onto a multimodal porous silica support; such supported chlorogallate(III) ionic liquids are reported for the first time. Supported chlorometallate(III) ionic liquids were used as recyclable heterogeneous catalysts for the Diels–Alder reaction under solventless conditions. High yields (99%) and high endo-selectivities (95%) were obtained after very short reaction times (5 min) at near-ambient temperature (25 °C).

Original language	English
Pages (from-to)	8129-8137
Journal	Catalysis Science & Technology
Volume	6
Issue number	22
Early online date	10 Oct 2016
DOIs	https://doi.org/10.1039/C6CY01771A
Publication status	Published - 21 Nov 2016

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Silica-supported chlorometallate(III) ionic liquids as recyclable catalysts for Diels–Alder reaction under solventless conditions
© The Royal Society of Chemistry 2016. This work is made available online in accordance with the publisher’s policies. Please refer to any applicable terms of use of the publisher.
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title = "Silica-supported chlorometallate(III) ionic liquids as recyclable catalysts for Diels–Alder reaction under solventless conditions",

abstract = "A range of Lewis acidic metal chlorides were tested as homogeneous catalysts in a model Diels–Alder reaction; AlCl3 and GaCl3 performed best in terms of conversion and endo : exo selectivity. Based on this outcome, the corresponding chlorometallate(III) ionic liquids were tested as homogeneous catalysts, without a decrease in performance compared to the chlorides. Finally, these ionic liquids were heterogenised by covalent tethering of the cation onto a multimodal porous silica support; such supported chlorogallate(III) ionic liquids are reported for the first time. Supported chlorometallate(III) ionic liquids were used as recyclable heterogeneous catalysts for the Diels–Alder reaction under solventless conditions. High yields (99%) and high endo-selectivities (95%) were obtained after very short reaction times (5 min) at near-ambient temperature (25 °C).",

author = "Karolina Matuszek and Anna Chrobok and Piotr Latos and Magdalena Markiton and Katarzyna Szymanska and Andrzej Jarzebski and Malgorzata Swadzba-Kwasny",

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AU - Matuszek, Karolina

AU - Chrobok, Anna

AU - Latos, Piotr

AU - Markiton, Magdalena

AU - Szymanska, Katarzyna

AU - Jarzebski, Andrzej

AU - Swadzba-Kwasny, Malgorzata

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Y1 - 2016/11/21

N2 - A range of Lewis acidic metal chlorides were tested as homogeneous catalysts in a model Diels–Alder reaction; AlCl3 and GaCl3 performed best in terms of conversion and endo : exo selectivity. Based on this outcome, the corresponding chlorometallate(III) ionic liquids were tested as homogeneous catalysts, without a decrease in performance compared to the chlorides. Finally, these ionic liquids were heterogenised by covalent tethering of the cation onto a multimodal porous silica support; such supported chlorogallate(III) ionic liquids are reported for the first time. Supported chlorometallate(III) ionic liquids were used as recyclable heterogeneous catalysts for the Diels–Alder reaction under solventless conditions. High yields (99%) and high endo-selectivities (95%) were obtained after very short reaction times (5 min) at near-ambient temperature (25 °C).

AB - A range of Lewis acidic metal chlorides were tested as homogeneous catalysts in a model Diels–Alder reaction; AlCl3 and GaCl3 performed best in terms of conversion and endo : exo selectivity. Based on this outcome, the corresponding chlorometallate(III) ionic liquids were tested as homogeneous catalysts, without a decrease in performance compared to the chlorides. Finally, these ionic liquids were heterogenised by covalent tethering of the cation onto a multimodal porous silica support; such supported chlorogallate(III) ionic liquids are reported for the first time. Supported chlorometallate(III) ionic liquids were used as recyclable heterogeneous catalysts for the Diels–Alder reaction under solventless conditions. High yields (99%) and high endo-selectivities (95%) were obtained after very short reaction times (5 min) at near-ambient temperature (25 °C).

U2 - 10.1039/C6CY01771A

DO - 10.1039/C6CY01771A

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JO - Catalysis Science & Technology

JF - Catalysis Science & Technology

IS - 22

ER -

Silica-supported chlorometallate(III) ionic liquids as recyclable catalysts for Diels–Alder reaction under solventless conditions

Abstract

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