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Selective Synthesis of anti-Bisbenzo[b]thieno[2,3-b:2',3'-e][1,4]dithiin via Copper-Catalyzed Domino Formation of
Wenyu Lai1, Xinrui Cui1, Kexin Xu1
1School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 101408, China.
Abstract:
A copper-catalyzed C-S bond-forming reaction of o-halophenylacetylenes selectively affords anti-bisbenzo[b]thieno[2,3-b:2',3'-e][1,4]dithiins (anti-BBTDs). This approach features a domino thienannulation reaction, a mild temperature, an inexpensive copper catalyst, efficient formation of C-S bonds, and excellent functional group compatibility. A domino thienannulation mechanism involving sulfur anions has been elucidated by an intermediate trapping experiment and X-ray photoelectron spectroscopy measurements. Furthermore, anti-BBTD derivatives with benzoyl substituents exhibit strong fluorescence and redox reversibility, which indicates their potential as optoelectronic materials.
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