Reagent Control Enables Selective and Regiodivergent Opening of Unsymmetrical Phenonium Ions

Shiyan Xu, Hannah M. Holst, Shelby B. McGuire and Nicholas J. Race*

*Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States, Email: nraceumn.edu

S. Xu, H. M. Holst, S. B. McGuire, N. J. Race, J. Am. Chem. Soc., 2020, 142, 8090-8096.

DOI: 10.1021/jacs.0c02095

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Abstract

SnCl₄ and TiCl₄ as Lewis acids and chloride nucleophiles enable selective and regiodivergent openings of unsymmetrical phenonium ions at either the substituted internal position (SnCl₄) or unsubstituted terminal position (TiCl₄). These reactions are highly selective, stereospecific, operationally simple, and proceed in good to excellent yields.

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proposed reaction pathways

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Key Words

chlorohydrins, chlorination

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ID: J48-Y2020