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Synthesis of 9-fluorenylidenes and 9,10-phenanthrenes through palladium-catalyzed aryne annulation by o-halostyrenes and o-halo allylic benzenes.

ABSTRACT: A number of functionally substituted 9-fluorenylidenes and 9,10-phenanthrenes have been synthesized from substituted o-halostyrenes and o-halo allylic benzenes respectively in good yields by the palladium-catalyzed annulation of arynes. The methodology tolerates a variety of functional groups, including cyano, ester, aldehyde, and ketone groups, occurs under relatively mild reaction conditions, and involves the generation of two new carbon-carbon bonds, thus providing these important carbocyclic ring systems in a single synthetic step.

SUBMITTER: Worlikar SA

PROVIDER: S-EPMC2791677 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Synthesis of 9-fluorenylidenes and 9,10-phenanthrenes through palladium-catalyzed aryne annulation by o-halostyrenes and o-halo allylic benzenes.

Worlikar Shilpa A SA Larock Richard C RC

The Journal of organic chemistry 20091201 23

A number of functionally substituted 9-fluorenylidenes and 9,10-phenanthrenes have been synthesized from substituted o-halostyrenes and o-halo allylic benzenes respectively in good yields by the palladium-catalyzed annulation of arynes. The methodology tolerates a variety of functional groups, including cyano, ester, aldehyde, and ketone groups, occurs under relatively mild reaction conditions, and involves the generation of two new carbon-carbon bonds, thus providing these important carbocyclic ...[more]

PMID: 19902957

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