Synthesis and Structural Analysis of 3,6-Diarylthieno[3,2-b]thiophenes by Site-selective Pd-catalyzed C-H Functionalization

Author(s): Nguyen Hien*, Dao Thi Nuong, Nguyen Hung-Huy.

Journal Name: Letters in Organic Chemistry

Volume 14 , Issue 10 , 2017

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Abstract:

Thieno[3,2-b]thiophene represents a typical core structure in a large number of organic optoelectronic materials and molecular magnetism. One-pot efficient approach to modify the electronic structure of thieno[3,2-b]thiophene is to introduce suitable substituents into this π- conjugated skeleton. In this paper, we report on a facile route to precisely functionalize thieno[3,2- b]thiophene by the direct Pd-catalyzed arylation reaction with boronic acids. Based on this procedure, a number of 3,6-diarylthieno[3,2-b]thiophenes were prepared in good yields. NMR methods and XRay crystal structure analysis confirmed high regioselectivities at the C-3 and C-6 positions of thieno[3,2-b]thiophene skeleton.

Keywords: C-H functionalization, cross-coupling, direct arylation, palladium catalysis, regioselectivity, thieno[3, 2-b]thiophene.

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Article Details

VOLUME: 14
ISSUE: 10
Year: 2017
Page: [758 - 763]
Pages: 6
DOI: 10.2174/1570178614666170608084820
Price: $58

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