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Programmed Site-Selective Palladium-Catalyzed Arylation of Thieno[3,2-b]thiophene. 2017

T M Ha Vuong, and Didier Villemin, and Hung-Huy Nguyen, and Tin Thanh Le, and Tung T Dang, and Hien Nguyen
Faculty of Applied Sciences, Ton Duc Thang University, 19 Nguyen Huu Tho Street, Tan Phong Ward, District 7, Ho Chi Minh City, Vietnam.

Mono-, di-, tri-, and tetraarylated thieno[3,2-b]thiophenes were synthesized by direct site-selective Pd-catalyzed C-H activation reactions with various aryl bromides in the presence of a phosphine-free Pd(OAc)2 /KOAc catalyst system in N,N-dimethylacetamide (DMAc). The arylation of 2-arylthieno[3,2-b]thiophene took place at the C3 position if the 2-aryl substituents possessed electron-withdrawing groups and at the C5 position if they were bulky and possessed electron-donating groups.

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