Reusable Cu2O-nanoparticle-catalyzed amidation of aryl iodides

Synlett

Volumn , Issue 20, 2009, Pages 3323-3327

  Jammi, Suribabu ^a   Krishnamoorthy, Sankarganesh ^a   Saha, Prasenjit ^a   Kundu, Dipti S ^a   Sakthivel, Sekarpandi ^a   Ali, Md Ashif ^a   Paul, Rajesh ^a   Punniyamurthy, Tharmalingam ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Amide; Aryl iodide; Cross coupling reaction; Cu2O nanoparticles; Heterogeneous catalysis

Indexed keywords

COPPER OXIDE; IODINE DERIVATIVE; NANOPARTICLE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMIDATION; ARTICLE; CATALYSIS; REACTION ANALYSIS; RECYCLING; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY;

EID: 72149109288     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218368     Document Type: Article

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52. 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 × 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 × mL) and acetone (3 × mL). After drying in vacuum, the Cu2O nanoparticles were reused for the fresh reaction of benzamide with 1-iodo- 4-methylbenzene.