Physical Sciences and Mathematics Commons^™

Synthesis Of 4-Methylbenzoate(2ʹ,4ʹ,6ʹ-Trimethoxyphenyl) Iodonium Tosylate, Thomas Ludwig Seidl, Aaron Moment, Charles Orella, Thomas Vickery, David R. Stuart

Chemistry Faculty Publications and Presentations

Hypervalent iodine continues to intrigue organic chemists with its diverse breadth of reactivity. The use of diaryliodonium salts as aryltransfer reagents has increased dramatically in the past decade as they have become more available by the development of efficient “one-pot” synthesis methods. Unsymmetrical diaryliodonium salts that selectively, and predictably, transfer one aryl group over the other are particularly desirable reagents, especially for the transfer of elaborate aryl groups to nucleophilic moieties. While the mesityl (Mes; 2,4,6-trimethylphenyl) group effectively serves as a general auxiliary in metal-catalyzed reactions of diaryliodonium salts, a broadly applicable auxiliary has not been adopted in metal-free reactions. …