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Silver nanoparticle-catalyzed Diels-Alder cycloadditions of 2'-hydroxychalcones.

ABSTRACT: Metal nanoparticles are currently being employed as catalysts for a number of classical chemical transformations. In contrast, identification of novel reactions of nanoparticles, especially toward the synthesis of complex natural products and derivatives, is highly underdeveloped and represents a bourgeoning area in chemical synthesis. Herein, we report silica-supported silver nanoparticles as solid, recyclable catalysts for Diels-Alder cycloadditions of 2'-hydroxychalcones and dienes in high yield and turnover number. The use of silver nanoparticle catalysts is further demonstrated by the total synthesis of the cytotoxic natural product panduratin A employing a highly electron-rich dienophile and Lewis acid sensitive diene.

SUBMITTER: Cong H

PROVIDER: S-EPMC2882859 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Silver nanoparticle-catalyzed Diels-Alder cycloadditions of 2'-hydroxychalcones.

Cong Huan H Becker Clinton F CF Elliott Sean J SJ Grinstaff Mark W MW Porco John A JA

Journal of the American Chemical Society 20100601 21

Metal nanoparticles are currently being employed as catalysts for a number of classical chemical transformations. In contrast, identification of novel reactions of nanoparticles, especially toward the synthesis of complex natural products and derivatives, is highly underdeveloped and represents a bourgeoning area in chemical synthesis. Herein, we report silica-supported silver nanoparticles as solid, recyclable catalysts for Diels-Alder cycloadditions of 2'-hydroxychalcones and dienes in high yi ...[more]

PMID: 20443601

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