An efficient heterogeneous gold(I)-catalyzed intermolecular cycloaddition of 2-aminoaryl carbonyls and internal alkynes leading to polyfunctionalized quinolines

Abstract

The first heterogeneous intermolecular cycloaddition of 2-aminoaryl carbonyls and internal alkynes was realized in DMF at 100 °C by using a triphenylphosphine-functionalized MCM-41-supported gold(I) complex [MCM-41-PPh₃-AuCl] and AgOTf as catalysts, yielding a variety of polyfunctionalized quinolines in good to excellent yields. This heterogeneous gold(I) complex could easily be prepared via a simple two-step procedure from commercially available reagents and recovered by filtration of the reaction mixture. The recovered catalyst could be reused at least seven times with almost consistent activity without addition of AgOTf as a cocatalyst.

Graphical Abstract

Keywords:

• Cycloaddition
• gold
• heterogeneous catalysis
• internal alkynes
• quinoline

Additional information

Funding

We thank the National Natural Science Foundation of China [No. 21462021], the Natural Science Foundation of Jiangxi Province of China [No. 20161BAB203086] and Key Laboratory of Functional Small Organic Molecule, Ministry of Education [No. KLFS-KF-201704] for financial support.