- Application of zirconacyclopentadienes (metalla-heterocycles) and cross-coupling for the convenient preparative method of 6,13-disubstituted pentacene
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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 γ-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.
- Jia, Zhiying,Li, Shi,Nakajima, Kiyohiko,Kanno, Ken-Ichiro,Song, Zhiyi,Takahashi, Tamotsu
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- 6,13-DIHALOGEN-5,14-DIHYDROPENTACENE DERIVATIVE AND METHOD FOR PRODUCING 6,13-SUBSTITUTED-5,14-DIHYDROPENTACENE DERIVATIVE USING SAME
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The present invention provides a 6,13-dihalogen-5,14-dihydropentacene derivative and a method for production thereof. Compounds (b) and (c) are reacted through cross-coupling reaction in the presence of a metal compound and a lithiating agent to synthesize compound (d), which is then halogenated to thereby obtain a 6,13-dihalogen-5,14-dihydropentacene derivative (compound (e)). [wherein X1 and X2 are each a halogen atom, and R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each a hydrogen atom, an optionally substituted C1-C20 hydrocarbon group, etc.]
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Paragraph 0151; 0152; 0153; 0154; 0155; 0156
(2013/04/10)
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