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Updated: Jan 6, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
General Light-Induced Pd-Catalyzed Allylic C-H Alkylation of Internal Alkenes: Direct Access to Tertiary and
Subham Pradhan1, Gaurav Prakash1, Vladimir Gevorgyan1
1Department of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, Texas 75080-3021, United States.
Abstract:
Tertiary and quaternary carbon centers containing allylic systems are prevalent in natural products and drugs. Among existing approaches toward these valuable motifs, a direct allylic C-H alkylation is the most straightforward approach, which bypasses the requirement for prefunctionalization of allylic substrates. However, existing methods suffer from limited scope both in terms of alkenes and carbon nucleophiles. Herein, we report a light-induced Pd catalyzed method that overcomes these challenges, enabling the coupling of diverse internal alkenes with a range of carbon pronucleophiles including those with pKa > 20. In addition, this method provides direct access to the construction of tertiary and quaternary carbon centers in enantioselective fashion.
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