Uncatalyzed zirconium-mediated biphenylation of o-dihalobenzenes to form triphenylenes.
The reaction of [Zr(biphe)3][(Li.(THF)4)2], where biphe is 2,2'-biphenyldiyl, with an o-dihaloarene produces a triphenylene. Two new bonds are created in this rare example of an uncatalyzed, Zr-mediated aryl-aryl bond formation. Multiple biphe fragments can be incorporated to give larger triphenylene-containing polycyclic aromatic hydrocarbons. This reaction can introduce significant strain and was demonstrated to tolerate alkyl and methoxy substituents.
Hilton
Cameron L
CL
Department of Chemistry, University of Nevada, Reno, NV 89577, USA.
Jamison
Christopher R
CR
King
Benjamin T
BT