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Updated: Jun 15, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Synthesis of 3,3-Disubstituted Allyl Isoindolinones via Pd-Catalyzed Decarboxylative Allylic Alkylation
Mario Alvarado1, Marisa Loo1, Hanna Adler1
1Department of Chemistry, Occidental College, Los Angeles, California 90041, United States.
Abstract:
Herein, we report a mild palladium-catalyzed decarboxylative allylic alkylation of allyl ester-substituted isoindolinone substrates to afford a variety of 3,3-disubstituted isoindolinone derivatives. The decarboxylative coupling reaction tolerates a range of functional groups, including ketones and alkenyl halides, and does not require protection of the isoindolinone nitrogen. Additionally, the reaction was found to proceed in near-quantitative yield for most substrates evaluated. Based on the isolation of competing cyclopropane and protonation products, a reaction mechanism is proposed.
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