2003 C-C bond formation

C-C bond formationO 0282 Dicationic Electrophiles from Olefinic Amines in Superacid. — Olefinic amines

and heterocycles (I), (IV) and (VI) react with the Broensted superacid TfOH to generate the corresponding dications which smoothly react with benzene to furnish adducts (III), (V) and (VII), respectively. Other aromatic compounds like toluene, chlorobenzene and even the deactivated arene dichlorobenzene (VIII) can also be used in this reaction, but nitrobenzene remains unchanged under the applied reaction conditions. Additionally, this reaction can be successfully used to functionalize polystyrene beads. — (ZHANG, Y.; MCELREA, A.; SANCHEZ, G. V. J.; DO, D.; GOMEZ, A.; AGUIRRE, S. L.; RENDY, R.; KLUMPP*, D. A.; J. Org. Chem. 68 (2003) 13, 5119-5122; Dep. Chem., Calif. State Polytech. Univ., Pomona, CA 91768, USA; Eng.) — Mischke

42- 055