1196708-17-4Relevant articles and documents
Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation
Ammann, Stephen E.,Rice, Grant T.,White, M. Christina
, p. 10834 - 10837 (2014)
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.
