Ligand-free N-arylation of heterocycles using metal-organic framework [Cu(INA)2] as an efficient heterogeneous catalystElectronic supplementary information (ESI) available. See DOI: 10.1039/c5ra24165k

• Main Authors: Truong, Thanh, Nguyen, Chi V, Truong, Ngoc T, Phan, Nam T. S
• Format: Journal Article
• Published: 18.12.2015
• ISSN: 2046-2069
• DOI: 10.1039/c5ra24165k

A metal-organic framework [Cu(INA) 2 ] was synthesized and used as a heterogeneous catalyst for arylation of a wide range of N-H heterocycles and aryl halides under ligand-free conditions. The N -arylation reaction involved the use of 5 mol% Cu-MOF catalyst with K 3 PO 4 or t BuOLi as the base in dimethylacetamide (DMA) solvent at 100 °C in 6 h. [Cu(INA) 2 ] exhibited higher catalytic activity for the N -arylation transformation than that of common homogeneous copper catalysts and other Cu-MOFs with unsaturated open metal sites such as Cu 2 (BDC) 2 (BPY), Cu 3 (BTC) 2 , and Cu 2 (BDC) 2 (DABCO). Interestingly, reaction conditions are compatible with a wide range of N-H heterocycles, functional groups, and aryl chlorides. A leaching test indicated no contribution of leached active species in the reaction filtrate. Furthermore, the [Cu(INA) 2 ] catalyst could be facilely separated from the reaction mixture and recovered and reused several times without a significant degradation in catalytic activity. A metal-organic framework [Cu(INA) 2 ] was synthesized and used as a heterogeneous catalyst for arylation of a wide range of N-H heterocycles and aryl halides under ligand-free conditions.