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Synthesis of Biindene Derivatives via Pd-Catalyzed Alkene Difunctionalization Reactions. | LitMetric

Synthesis of Biindene Derivatives via Pd-Catalyzed Alkene Difunctionalization Reactions.

Org Lett

Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.

Published: May 2024

AI Article Synopsis

Article Abstract

The palladium-catalyzed cross-coupling of 2-allylphenyl triflate and related electrophiles with substituted indenes affords biindene derivatives in moderate to good yields with high selectivity for thermodynamically preferred alkene isomers. The transformations involve alkene nucleopalladation with indenyl anions, and we also demonstrate that 2-allylphenyl triflates can be transformed to indenes under similar conditions. The scope of this transformation, along with the mechanism of formation of both indene and biindene products, is described.

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Source
http://dx.doi.org/10.1021/acs.orglett.4c01400DOI Listing

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