Chemistry

Silver Surprise

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Science  04 Jun 2010:
Vol. 328, Issue 5983, pp. 1208-1209
DOI: 10.1126/science.328.5983.1208-d

Precious-metal nanoparticles are potent catalysts for oxidation and reduction reactions of commodity chemical compounds. Cong et al. have now discovered that silver nanoparticles also efficiently catalyze the Diels-Alder cycloaddition of dienes to hydroxychalcones, a broadly useful transformation for synthesizing more complex organic molecules of potential interest in medicinal research. Preliminary screening of a series of silver salts mixed with borohydride revealed the surprising catalytic capacity of the elemental particles formed in situ. The authors then optimized the preparation by supporting the catalytic particles on silica, and highlighted the utility of the system through its application in the synthesis of the natural product panduratin A. Electron paramagnetic resonance spectroscopy applied in tandem with a radical probe supported a mechanism relying on single-electron transfer from adsorbed chalcone to the silver particle.

J. Am. Chem. Soc. 132, 10.1021/ja102482b (2010).

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