APPLICATION OF ZIRCONACYCLOPENTADIENES (METALLA-HETEROCYCLES) AND CROSS-COUPLING FOR THE CONVENIENT PREPARATIVE METHOD OF 6,13-DISUBSTITUTED PENTACENE

作者：Jia Zhiying^*; Li Shi; Nakajima Kiyohiko; Kanno Ken ichiro; Song Zhiyi; Takahashi Tamotsu

来源：Heterocycles, 2012, 86(2): 1495-1506.

DOI：10.3987/COM-12-S(N)130

• Zirconacyclopentadiene
• Diiododihydropentacene
• Cross-Coupling
• Aromatization
• Pentacene

Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14-dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and gamma-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.

• 出版日期2012-12-31