title: Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation.
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.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign , Urbana, Illinois 61801, United States.
authors.forename: Stephen E
authors.initials: SE
authors.lastname: Ammann
authors.forename: Grant T
authors.initials: GT
authors.lastname: Rice
authors.forename: M Christina
authors.initials: MC
authors.lastname: White
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*
chemical_list: D000475:Alkenes; D002839:Chromans; D011714:Pyrans; D010165:Palladium