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Terminal Olefins to Chromans, Isochromans, and Pyrans via Allylic C-H Oxidation

Stephen E. Ammann, Grant T. Rice and M. Christina White*

*Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, United States, Email: whitescs.uiuc.edu

S. E. Ammann, G. T. Rice, M. C. White, J. Am. Chem. Soc., 2014, 136, 10834-10837.

DOI: 10.1021/ja503322e (free Supporting Information)


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Abstract

A combination of Pd(II)/bis-sulfoxide C-H activation and Lewis acid co-catalysis enables the synthesis of chroman, isochroman, and pyran motifs from a wide range of alcohols. Mechanistic studies suggest that the reaction proceeds via initial C-H activation followed by a novel inner-sphere functionalization pathway.

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Key Words

cyclic ethers, tetrahydropyrans, BQ


ID: J48-Y2014