Imidazolium-Based Ionic Liquids Catalyzed Formylation of Amines Using Carbon Dioxide and Phenylsilane at Room Temperature

Leiduan Hao; Yanfei Zhao; Bo Yu; Zhenzhen Yang; Hongye Zhang; Buxing Han; Xiang Gao; Zhimin Liu

doi:10.1021/acscatal.5b01274

Imidazolium-Based Ionic Liquids Catalyzed Formylation of Amines Using Carbon Dioxide and Phenylsilane at Room Temperature

Leiduan Hao, Yanfei Zhao, Bo Yu, Zhenzhen Yang, Hongye Zhang, Buxing Han, Xiang Gao, Zhimin Liu

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

176 Scopus citations

Abstract

The CO₂-involved synthesis of chemicals is of significance. In this work, we found that 1-alkyl-3-methylimidazolium ionic liquids (ILs) had high efficiency for catalyzing the formylation of amines using CO₂ and phenylsilane at room temperature, producing the corresponding formylated products in excellent yields under the metal-free condition. The ILs acted as bifunctional catalysts, which activated the Si-H bond of phenylsilane to react with CO₂ to form the formoxysilane intermediate and simultaneously activated the amine substrate through the hydrogen bond. Moreover, the imidazolium cation and the anions of the ILs showed an excellent synergistic effect on catalyzing the formylation of amines.

Original language	English
Pages (from-to)	4989-4993
Number of pages	5
Journal	ACS Catalysis
Volume	5
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.5b01274
State	Published - Jul 28 2015
Externally published	Yes

Funding

Funders	Funder number
National Natural Science Foundation of China	21321063, 21125314, 21403252

Keywords

carbon dioxide
conversion
formylation
ionic liquid
room temperature

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acscatal.5b01274

Cite this

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title = "Imidazolium-Based Ionic Liquids Catalyzed Formylation of Amines Using Carbon Dioxide and Phenylsilane at Room Temperature",

abstract = "The CO2-involved synthesis of chemicals is of significance. In this work, we found that 1-alkyl-3-methylimidazolium ionic liquids (ILs) had high efficiency for catalyzing the formylation of amines using CO2 and phenylsilane at room temperature, producing the corresponding formylated products in excellent yields under the metal-free condition. The ILs acted as bifunctional catalysts, which activated the Si-H bond of phenylsilane to react with CO2 to form the formoxysilane intermediate and simultaneously activated the amine substrate through the hydrogen bond. Moreover, the imidazolium cation and the anions of the ILs showed an excellent synergistic effect on catalyzing the formylation of amines.",

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T1 - Imidazolium-Based Ionic Liquids Catalyzed Formylation of Amines Using Carbon Dioxide and Phenylsilane at Room Temperature

AU - Hao, Leiduan

AU - Zhao, Yanfei

AU - Yu, Bo

AU - Yang, Zhenzhen

AU - Zhang, Hongye

AU - Han, Buxing

AU - Gao, Xiang

AU - Liu, Zhimin

PY - 2015/7/28

Y1 - 2015/7/28

N2 - The CO2-involved synthesis of chemicals is of significance. In this work, we found that 1-alkyl-3-methylimidazolium ionic liquids (ILs) had high efficiency for catalyzing the formylation of amines using CO2 and phenylsilane at room temperature, producing the corresponding formylated products in excellent yields under the metal-free condition. The ILs acted as bifunctional catalysts, which activated the Si-H bond of phenylsilane to react with CO2 to form the formoxysilane intermediate and simultaneously activated the amine substrate through the hydrogen bond. Moreover, the imidazolium cation and the anions of the ILs showed an excellent synergistic effect on catalyzing the formylation of amines.

AB - The CO2-involved synthesis of chemicals is of significance. In this work, we found that 1-alkyl-3-methylimidazolium ionic liquids (ILs) had high efficiency for catalyzing the formylation of amines using CO2 and phenylsilane at room temperature, producing the corresponding formylated products in excellent yields under the metal-free condition. The ILs acted as bifunctional catalysts, which activated the Si-H bond of phenylsilane to react with CO2 to form the formoxysilane intermediate and simultaneously activated the amine substrate through the hydrogen bond. Moreover, the imidazolium cation and the anions of the ILs showed an excellent synergistic effect on catalyzing the formylation of amines.

KW - carbon dioxide

KW - conversion

KW - formylation

KW - ionic liquid

KW - room temperature

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Imidazolium-Based Ionic Liquids Catalyzed Formylation of Amines Using Carbon Dioxide and Phenylsilane at Room Temperature

Abstract

Funding

Keywords

UN SDGs

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