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Updated: Mar 18, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ru(II)-Catalyzed peri-C-H Activation with Strained Alkylidene β-Lactones and β-Lactams: Selective Access to Seven-
Sudeshna Mondal1, Prabhudatta Behura1, Suman Dana1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.
Abstract:
A Ru(II)-catalyzed peri-C-H activation of α-naphthols with strained alkylidene β-lactones and β-lactams is reported. With alkylidene β-lactones, the reaction proceeds via controlled strain release, favoring an allylic substitution pathway to afford a broad range of seven-membered oxepines in high yields. In contrast, the corresponding β-lactams suppress this reactivity and undergo Heck-type functionalization, leading to functionalized β-lactams. The protocol is operationally simple and scalable, displays a broad substrate scope, and can be extended to distal functionalization of indoles. The synthetic utility of this method is highlighted through downstream product diversification, which further enhances the scaffold diversity.
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