Copper(II) Acetate/1,4-Diphenyl-1,4-diazabuta-1,3-diene Catalyzed Sonogashira Cross-Coupling of Aryl Halides with Terminal Alkynes under Aerobic and Solvent-Free Conditions

Abstract

The Sonogashira cross-coupling of aryl halides with terminal alkynes catalyzed by an inexpensive copper(II) acetate/1,4-diphenyl-1,4-diazabuta-1,3-diene [Cu(OAc)₂/DAB-Ph] catalytic system is reported. A series of ligands, including diazabutadiene systems, N,N-dimethylglycine, l-proline, ethylenediamine, and phosphines, were evaluated, and 1,4-diphenyl-1,4-diazabuta-1,3-diene provided the best results. In the presence of copper(II) acetate (10 mol%), 1,4-diphenyl-1,4-diazabuta-1,3-diene (20 mol%), and tetrabutylammonium fluoride (3 equiv), a number of aryl iodides or bromides were treated smoothly with alkynes to afford the corresponding products in moderate to excellent yields. It is noteworthy that the reaction is conducted under aerobic and solvent-free conditions.

Key words

copper(II) acetate - diazabutadiene - Sonogashira cross-coupling reaction - aryl halide - terminal alkyne

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