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

[ Vol. 14 , Issue. 10 ]

Author(s):

Nguyen Hien*, Dao Thi Nuong and Nguyen Hung-Huy   Pages 758 - 763 ( 6 )

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.

Affiliation:

Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Ha Noi, Department of Chemistry, Hanoi National University of Education, Hanoi, Department of Chemistry, VNU - Hanoi University of Science, 19 Le Thanh Tong Street, Ha Noi

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