A Forgotten Olefin: A Convenient One-pot Cascade Reaction Involving Suzuki-Miyaura and Mizoroki-Heck Couplings to Form (E)-1,2-Di(pyren-1-yl)ethylene

作者:Yamashita Ken ichi; Kimura Keisuke; Tazawa Shin; Asano Motoko S; Sugiura Ken ichi*
来源:Chemistry Letters, 2011, 40(12): 1459-1461.
DOI:10.1246/cl.2011.1459

摘要

The addition of 0.5 equiv of vinylboronic acid pinacol ester I to 1-bromopyrene derivative 3 in the presence of [Pd(PPh3)(4)] and K2CO3 induced a cascade reaction involving Suzuki-Miyaura and Mizoroki-Heck couplings and afforded (E)-1,2-di(pyren-1-yl)ethylene derivative 1b. An alternative synthesis of 1b was carried out by an olefin metathesis. Formed 1b showed absorption bands in the visible region and a low oxidation potential attributable to a narrow HOMO-LUMO gap.

  • 出版日期2011-12-5