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Updated: Apr 27, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation
Stephen E Ammann1, Grant T Rice, M Christina White
1Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign , Urbana, Illinois 61801, United States.
Abstract:
The synthesis of chroman, isochroman, and pyran motifs has been accomplished via a combination of Pd(II)/bis-sulfoxide C-H activation and Lewis acid co-catalysis. A wide range of alcohols are found to be competent nucleophiles for the transformation under uniform conditions (catalyst, solvent, temperature). Mechanistic studies suggest that the reaction proceeds via initial C-H activation followed by a novel inner-sphere functionalization pathway. Consistent with this, the reaction shows reactivity trends orthogonal to those of traditional Pd(0)-catalyzed allylic substitutions.
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