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May 14, 2010

Silver Spurs Cycloadditions

Nanoparticles make their debut as catalysts for organic synthesis in a Diels-Alder reaction

Bethany Halford

The long, thin silver nanowires shown in this SEM image could lead to improved transparent electrodes.
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Nanoparticles have been all the rage in chemistry for years, but synthetic organic chemists have been slow to take up the trend. Now, John A. Porco Jr. and coworkers at Boston University are reporting the first example of a Diels-Alder cycloaddition catalyzed by metal nanoparticles (J. Am. Chem. Soc., DOI: 10.1021/ja102482b). Porco’s group was working on the total synthesis of panduratin A—a natural product with promising anticancer, anti-HIV, and anti-inflammatory activities—when it ran into trouble getting the key Diels-Alder reaction to work. The team screened metal salts in combination with borohydride as catalysts and found that AgBF4 worked best. Several observations led the researchers to conclude that they were generating silver nanoparticles in solution, so they created a heterogeneous catalyst by fixing the in situ-generated nanoparticles onto silica gel. This material catalyzed the critical Diels-Alder reaction in 85% yield, producing predominately the desired endo isomer. The reaction was conducted in air without the need for excluding water or oxygen. Furthermore, the catalyst can be stored on the benchtop for months and recycled without significant loss of activity.

Chemical & Engineering News
ISSN 0009-2347
Copyright © 2011 American Chemical Society
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