Synthesis of extended triphenylenes by palladium-catalyzed [2+2+2] cycloaddition of triphenylynes.
The synthesis of ortho-(trimethylsilyl)triphenylenyl triflates 7 is described. Fluoride-induced decomposition of these triflates leads to the generation of didehydrotriphenylenes (triphenylynes) 6. These arynes undergo [4+2] cycloadditions with dienes to afford the corresponding Diels-Alder adducts or palladium-catalyzed formal [2+2+2] cycloadditions to afford extended triphenylenes.
Romero
Carmen
C
Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Peña
Diego
D
Pérez
Dolores
D
Guitián
Enrique
E
D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*
D006841:Hydrocarbons, Aromatic; D010165:Palladium