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Bidirectional iterative synthesis of alternating benzene-furan oligomers towards molecular wires
Chin-Fa Lee1, Ching-Yuan Liu, Hua-Can Song
1Institute of Chemistry, Academia Sinica, Department of Chemistry, National Taiwan University, Taipei, Taiwan.
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.
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