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 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.
Lee
Chin-Fa
CF
Institute of Chemistry, Academia Sinica, Department of Chemistry, National Taiwan University, Taipei, Taiwan.
Liu
Ching-Yuan
CY
Song
Hua-Can
HC
Luo
Shr-Jie
SJ
Tseng
Jui-Chang
JC
Tso
Hsi-Hua
HH
Luh
Tien-Yau
TY