We report the first examples of selective and regiodivergent opening of unsymmetrical phenonium ions with chloride ions. These reactions are enabled by the dual role of SnCl4 and TiCl4 as Lewis acids and chloride nucleophiles. Reagent control dictates addition of chloride at either the substituted internal position (SnCl4) or unsubstituted terminal position (TiCl4) of the phenonium ion. These reactions are highly selective, stereospecific, operationally simple, and proceed in good to excellent yields. Diverse product utility is demonstrated.
Bibliographical noteFunding Information:
This work was funded by the University of Minnesota and the American Chemical Society Petroleum Research Fund (PRF 60782-DNI1). We thank Professors Topczewski, Tonks, and Roberts (UMN) for insightful discussions. The Topczewski lab is thanked for supplying chemicals and assistance with SFC/HPLC analysis. We thank Dr. Victor G. Young, Jr., and the X-ray Crystallographic Laboratory at the University of Minnesota for crystallographic analysis of 6z , 7c , and 9ac .
PubMed: MeSH publication types
- Journal Article
- Research Support, Non-U.S. Gov't