Heterogenized Gold(I), Gold(III), and Palladium(II) Complexes for C-C Bond Reactions

 

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Abstract

Recycling of heterogenized gold(I), gold(III), and palladium(II) complexes could be achieved for Suzuki and Sonogashira cross-coupling reaction between iodo benzene and arylboronic ­acids or alkynes. Au(I) and Pd(II) afford selectively nonsymmetrical biaryl compounds, while gold(III) complexes can only catalyze the arylboronic or alkynes homocoupling. Recycling occurs without loss of the catalytic activity after several reaction cycles.

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Suzuki: the reaction was carried out in a 25 mL vessel, at 130 °C in a time range of 3-24 h. In a typical run, a mixture of aryl halide (10 mmol), boronic acid (15 mmol), aq K₃PO₄ (20 mmol), and catalyst (10-20 mol%) in 3 mL of o-xylene was stirred for the desired time. The solution was allowed to cool, and a 1:1 mixture of Et₂O-H₂O (20 mL) was added. The organic layer was washed, separated, further washed with another 10 mL portion of Et₂O, dried with anhyd MgSO₄, and filtered. The solvent and volatiles were completely removed under vacuum to give the crude product which subjected to column chromatographic separation resulted in pure compounds. The reaction was followed by GC-MS. At the end of the process, the mixture of reaction was filtered; the residue of support-containing catalyst washed to completely remove the remains of products and/or reactants and used again.

Sonogashira: The reaction was carried out in a 25 mL vessel, at 130 °C during 24 h. In a typical run, a mixture of aryl halide (10 mmol), alkyne (15 mmol), aq K₂CO₃ or K₃PO₄ (20 mmol) and catalyst (10-20 mol%) in 3 mL of o-xylene was stirred for the desired time. The reaction was followed by GC-MS. At the end of the process, the mixture of reaction was filtered; the residue of support-containing catalyst washed to completely remove the remains of products and/or reactants, and used again.