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Publication Details:

Title: Palladium-Catalyzed Regioselective Arylalkenylation of Ynamides

Author(s)Rajeshwer Vanjari, Shubham Dutta, Shengwen Yang, Vincent Gandon, and Akhila K. Sahoo* : Org. Lett., Org. Lett. 2022, 24, 1524–1529.
Journal NameOrganic Letters
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More Details:

A cationic palladium-catalyzed arylalkenylation of ynamides is presented. The putative keteniminium arylpalladium intermediate likely dictates the regioselective carbopalladation of the ynamide to form a vinylpalladium species. The capture of this complex by the olefin yields linear conjugated β-alkenyl aminodienes (especially with trans selectivity). The transformation features a broad scope with labile functional group tolerance and makes 42 unusual molecular scaffolds with structural diversity. DFT studies provide valuable insights into the reaction mechanism.