Synthesis and Functionalization of 3,3′-Bis(spirodienone)-Bridged 2,2′-Bithiophene: A New Building Block for Redox-Active Molecular Switching Materials

Bithiophene derivatives bridged with a bis(spirodienone) unit were synthesized and characterized. Lithiation of the thiophene rings of an unsubstituted derivative proceeded without decomposition of the bis(spirodienone) skeleton. Palladium-catalyzed cross-coupling reactions (Suzuki−Miyaura, Sonogash...

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Bibliographic Details
Published in:Organic letters 2008-09, Vol.10 (17), p.3837-3840
Main Authors: Kurata, Hiroyuki, Kim, Sang, Fujimoto, Takahisa, Matsumoto, Kouzou, Kawase, Takeshi, Kubo, Takashi
Format: Article
Language:English
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Summary:Bithiophene derivatives bridged with a bis(spirodienone) unit were synthesized and characterized. Lithiation of the thiophene rings of an unsubstituted derivative proceeded without decomposition of the bis(spirodienone) skeleton. Palladium-catalyzed cross-coupling reactions (Suzuki−Miyaura, Sonogashira) with bromides afforded a variety of π-extended derivatives. Bond breaking and formation under redox conditions were observed by cyclic voltammetry.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8015379