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. 2017 Oct 20;82(20):10920-10927.
doi: 10.1021/acs.joc.7b01745. Epub 2017 Sep 28.

Ullmann-Type Intramolecular C-O Reaction Toward Thieno[3,2-b]furan Derivatives with up to Six Fused Rings

Daoliang Chen  1   2 , Dafei Yuan  1   2 , Cheng Zhang  1   2 , Hao Wu  1   2 , Jianyun Zhang  1   2 , Baolin Li  1 , Xiaozhang Zhu  1   2
Affiliations

Ullmann-Type Intramolecular C-O Reaction Toward Thieno[3,2-b]furan Derivatives with up to Six Fused Rings

Daoliang Chen et al. J Org Chem. .

Abstract

A new strategy for the efficient synthesis of thieno[3,2-b]benzofuran derivatives (15 examples) was achieved on the basis of successive regioselective intermolecular Suzuki and newly developed intramolecular Ullmann C-O reactions in up to a 70% overall yield. The fast intramolecular C-O reaction can be realized by an efficient catalytic combination of CuI/1,10-phenanthroline in up to a 97% yield. This method is suitable for the construction of highly fused thieno[3,2-b]furan-containing heterocycles including DTBDF and TTDBF. The π-π and hydrogen-bonding interactions observed for the C8-DTBDF single crystal suggest its great potential for OFET applications in the near future.

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