Issue 23, 2002
From the journal:

Chemical Communications

Bidirectional iterative synthesis of alternating benzene–furan oligomers towards molecular wires†

Chin-Fa Lee,ab   Ching-Yuan Liu,b   Hua-Can Song,ab   Shr-Jie Luo,a   Jui-Chang Tseng,ab   Hsi-Hua Tsoa  and  Tien-Yau Luh*ab  

* Corresponding authors

a Institute of Chemistry, Academia Sinica, Taipei, Taiwan

b Department of Chemistry, National Taiwan University, Taipei, Taiwan
E-mail: tyluh@chem.sinica.edu.tw
Fax: +886-2-2651-1488
Tel: +886-2-2789-8500

Abstract

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.

Graphical abstract: Bidirectional iterative synthesis of alternating benzene–furan oligomers towards molecular wires

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Article information

DOI
https://doi.org/10.1039/B207881C
Article type
Communication
Submitted
12 Aug 2002
Accepted
10 Oct 2002
First published
28 Oct 2002

Chem. Commun., 2002, 2824-2825

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

C. Lee, C. Liu, H. Song, S. Luo, J. Tseng, H. Tso and T. Luh, Chem. Commun., 2002, 2824 DOI: 10.1039/B207881C

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