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

ChinFa Lee | Zendy; ChingYuan Liu | Zendy; HuaCan Song | Zendy; Shr-Jie Luo | Zendy; JuiChang Tseng | Zendy; Hsi-Hua Tso | Zendy; TienYau Luh | Zendy

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

Author(s) -

ChinFa Lee,

ChingYuan Liu,

HuaCan Song,

Shr-Jie Luo,

JuiChang Tseng,

Hsi-Hua Tso,

TienYau Luh

Publication year - 2002

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/b207881c

Subject(s) - furan , sonogashira coupling , alkene , yield (engineering) , benzene , chemistry , conjugated system , alkyne , combinatorial chemistry , annulation , organic chemistry , photochemistry , materials science , palladium , catalysis , polymer , metallurgy

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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