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Updated: Sep 17, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Vinyl-to-Acyl 1,5-Palladium Shift Enabled Amidation and Esterification of Aldehydes
Yaru Fang1, Qifan Guan1, Meiyu Chen1
1Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081, China.
Abstract:
We report an unprecedented synthetic route to dihydrobenzofuran and indoline acyl compounds via vinyl-to-acyl 1,5-palladium migration. This transformation is initiated by alkyne insertion, triggering the key 1,5-palladium migration to generate reactive acyl palladium intermediates. These intermediates undergo efficient trapping by amines and alcohols to afford the corresponding amide and ester-type products. Notably, the product can be further elaborated to construct eight-membered lactam scaffolds with significant pharmaceutical potential, highlighting the broad utility of this strategy in complex molecule synthesis.
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