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Synlett 2009(20): 3323-3327  
DOI: 10.1055/s-0029-1218368
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© Georg Thieme Verlag Stuttgart ˙ New York

Reusable Cu2O-Nanoparticle-Catalyzed Amidation of Aryl Iodides

Suribabu Jammi, Sankarganesh Krishnamoorthy, Prasenjit Saha, Dipti S. Kundu, Sekarpandi Sakthivel, Md Ashif Ali, Rajesh Paul, Tharmalingam Punniyamurthy*
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
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Publication History

Received 2 September 2009
Publication Date:
27 November 2009 (online)

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Abstract

The amidation of aryl iodides using Cu2O nanoparticles is described. It is a heterogeneous process, no leaching of the Cu2O species occurs, and the catalyst can be recovered and recycled without loss of activity.

Key words

Cu2O nanoparticles - heterogeneous catalysis - cross-coupling reaction - amide - aryl iodide

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General Procedure for Amidation of Aryl Iodides
Aryl iodide (1 mmol), amide (1.2 mmol), and CuI (10 mol%) were stirred at 120 ˚C in the presence of KOH (1 mmol) in PEG4000 (1 g) under N2 atmosphere. Progress of the reaction was monitored by TLC. After completion, the reaction flask was cooled to r.t., and the reaction mixture was treated with EtOAc (10 mL). The resulting solution was washed with H2O (3 × 2 mL). Drying (Na2SO4) and evaporation of the solvent gave a residue that was purified on a short pad of silica gel using hexane and EtOAc as eluent. All the isolated products were characterized by IR, ¹H NMR, and ¹³C NMR spectroscopy, and elemental analysis. Recyclability Experiment 1-Iodo-4-methylbenzene (5 mmol), benzamide (6 mmol), and CuI (10 mol%) were stirred at 120 ˚C in the presence of KOH (7.5 mmol) in PEG4000 (5 g) under N2 atmosphere. After the reaction, the reaction material was treated with EtOAc (10 mL) and H2O (5 mL). The aqueous layer having the Cu2O nanoparticles were centrifuged, and the precipitate was washed with deionized H2O (3 ¥ 2 mL) and acetone (3 ¥ 2 mL). After drying in vacuum, the Cu2O nanoparticles were reused for the fresh reaction of benzamide with 1-iodo-4-methylbenzene.