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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Aerobic Acylarylation of α,β-Unsaturated Amides with Aldehydes
Promita Biswas1, Subhasis Mandal1, Joyram Guin1
1School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India.
Abstract:
Herein, we illustrate that molecular oxygen (O2) is capable of promoting oxidative radical acylarylation of olefins with aliphatic aldehydes to afford acylated oxindoles in good yield (up to 97%). The key aspect of the process is the utilization of aldehyde auto-oxidation in developing aerobic radical olefin acylarylation. Kinetic studies confirm a lag phase for the reaction. Synthetic utility of the method is apparent via the preparation of biologically potent spirocyclic oxindoles and tetrahydrofuranoindolines.
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