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DOI: 10.1055/s-0040-1706420
Revisiting the ‘Phenonium Phenomenon’: Regiodivergent Opening of Nonsymmetrical Phenonium Ions with Halide Nucleophiles
This work was funded by the University of Minnesota and the American Chemical Society Petroleum Research Fund (PRF 60782-DNI1).Publication History
Received: 13 July 2020
Accepted after revision: 20 July 2020
Publication Date:
28 August 2020 (online)
◊ Indicates equal contribution
Abstract
Formation of phenonium ions through anchimeric assistance (neighboring-group participation) of aryl rings has been known since 1949. Although these reactive intermediates have been studied extensively by physical organic chemists, their potential as control elements in synthesis is underutilized. Presented here are our laboratory’s recently reported first examples of regiodivergent openings of nonsymmetrical phenonium ions with chloride nucleophiles. The selectivity of these processes is under reagent control. The reactions are operationally simple and permit the stereospecific synthesis of complex chiral building blocks from readily accessible epoxide starting materials.
1 Introduction
2 Select Examples of Phenonium Ion Methodology
3 Regiodivergent Opening of Nonsymmetrical Phenonium Ions
4 Summary and Outlook
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