Modular Synthesis of gamma‑Valerolactone-Based Ionic Liquids and Their Application as Alternative Media for Copper-Catalyzed Ullmann-type Coupling Reactions

Orha, László and Tukacs, József M. and Gyarmati, Benjámin and Szilágyi, András and Kollár, László and Mika, László T. (2018) Modular Synthesis of gamma‑Valerolactone-Based Ionic Liquids and Their Application as Alternative Media for Copper-Catalyzed Ullmann-type Coupling Reactions. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 6. pp. 5097-5104. ISSN 2168-0485

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Abstract

A convenient procedure was developed for the manufacturing of partially bio-ionic liquids (ILs) from renewable γ- valerolactone (GVL) and cheap and readily available tetraalkylphosphonium bromides with excellent (>99%) yields. The novel ionic liquids were characterized by their temperature dependent vapor pressure, density, viscosity, and conductivity. We have proven that these ILs can be a useful medium for copper-catalyzed Ullmann-type coupling reactions without the use of any ligand or additive, representing an environmentally benign tool for the synthesis of various amines. Twenty cross-coupling products were isolated with good to excellent yields (50−87%).

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