Bidirectional iterative synthesis of alternating benzene-furan oligomers towards molecular wires

Reaction of propargylic dithioacetal 2a with BuLi gives the sulfur-substituted allenyllithium 3a which is allowed to react with a dialdehyde to yield the corresponding alternating benzene-furan oligoaryls 6. Functional group transformation converts the ester groups in 6 to dialdehyde 8 which can be...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2002-01 (23), p.2824-2825
Main Authors: Lee, Chin-Fa, Liu, Ching-Yuan, Song, Hua-Can, Luo, Shr-Jie, Tseng, Jui-Chang, Tso, Hsi-Hua, Luh, Tien-Yau
Format: Article
Language:English
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Summary:Reaction of propargylic dithioacetal 2a with BuLi gives the sulfur-substituted allenyllithium 3a which is allowed to react with a dialdehyde to yield the corresponding alternating benzene-furan oligoaryls 6. Functional group transformation converts the ester groups in 6 to dialdehyde 8 which can be used for the synthesis of higher homologues towards molecular wires. A combination of this furan annulation, Heck reaction and Sonogashira coupling leads to a variety of benzene-furan-alkene/alkyne conjugated oligomers of precise length.
ISSN:1359-7345
1364-548X
DOI:10.1039/b207881c