Beilstein Journal of Organic Chemistry
Imides -- Arylation, Diaryliodonium, Hypercoordinate iodine, Metal-free, C–N coupling
Herein, we describe the synthesis of N-aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl(TMP)iodonium tosylate salts. The aryl transfer from the iodonium moiety occurs under electronic control with the electronrich trimethoxyphenyl group acting as a competent dummy ligand. The yields of N-aryl phthalimides are moderate to high and the coupling reaction is compatible with electron-deficient and sterically encumbered aryl groups.
Basu, Souradeep, Alexander H. Sandtorv, and David R. Stuart. "Imide arylation with aryl (TMP) iodonium tosylates." Beilstein Journal of Organic Chemistry 14, no. 1 (2018): 1034-1038.