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Updated: May 22, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Catalytic stereoselective synthesis of all-carbon tetra-substituted alkenes via Z-selective alkyne
Prashant S Shinde1, Valmik S Shinde1,2, Magnus Rueping1
1KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST) Thuwal 23955-6900 Saudi Arabia magnus.rueping@kaust.edu.sa.
Abstract:
We report a Ni-catalyzed cascade reaction leading to the arylation of an alkyne-induced acyl migration and the formation of all-carbon tetra-substituted alkenes in good yields with exclusive Z-selectivity. This transformation involves the generation of a nucleophilic vinyl-Ni species through regioselective syn-aryl nickelation of the alkynes, followed by an intramolecular acyl migration. The steric and electronic properties of the phosphine ligands are crucial for achieving high regio- and stereocontrol in this migratory carbo-acylation process. The synthetic utility of the resulting Z-tetra-substituted alkenes is also demonstrated.
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