Selective alternate derivatization of the hexaphenylbenzene framework through a thermodynamically controlled halogen dance.
We report a practical synthetic protocol and mechanistic details for the selective alternate derivatization of the hexaphenylbenzene (HPB) framework through a thermodynamically controlled halogen dance. The stability of the alternately trilithiated species of HPB is interpreted by the through-space interaction at the ipso-carbons of the phenyl groups of the HPB framework. By using this approach, C3-symmetric and lower-symmetric HPB derivatives possessing two or three kinds of substituents on the periphery have become easily and practically available.
Department of Integrated Sciences, Graduate School of Arts and Sciences, The University of Tokyo , 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan.
Tatsuo
T
Kojima
Shuichi
S
Hiraoka