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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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
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cited_by cdi_FETCH-LOGICAL-a379t-556ed1c9ade9774e4cda98f23587c2d3aa412473f8aa0d988e4d4e56e502156d3
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description 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.
doi_str_mv 10.1021/ol8015379
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title Synthesis and Functionalization of 3,3′-Bis(spirodienone)-Bridged 2,2′-Bithiophene: A New Building Block for Redox-Active Molecular Switching Materials
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