Highly Active CO2 Fixation into Cyclic Carbonates Catalyzed by Tetranuclear Aluminum Benzodiimidazole-Diylidene Adducts

Abstract

A set of tetranuclear alkyl aluminum adducts 1 and 2 supported by benzodiimidazole-diylidene ligands L1, N,N’-(1,5-diisopropylbenzodiimidazole-2,6-diylidene)bis(propan-2-amine), and L2, N,N’-(1,5-dicyclohexyl-benzodiimidazole-2,6-diylidene)dicyclohexanamine were synthetized in exceptional yields and characterized by spectroscopic methods. These compounds were studied as catalysts for cyclic carbonate formation (3a–o) from their corresponding terminal epoxides (2a–o) and carbon dioxide utilizing tetrabutylammonium iodide as a nucleophile in the absence of a solvent. The experiments were carried out at 70 °C and 1 bar CO2 pressure for 24 h and adduct 1 was the most efficient catalyst for the synthesis of a large variety of monosubstituted cyclic carbonates with excellent conversions and yields.