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Synfacts 2011(10): 1075-1075  
DOI: 10.1055/s-0030-1261208
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Dibenzotetrathienocoronenes and Hexabenzocoronene in Three Steps

Contributor(s): Timothy M. Swager, Olesya Haze
C.-Y. Chiu, B. Kim, A. Gorodetsky, W. Sattler, S. Wei, A. Sattler, M. Steigerwald, C. Nuckolls*
Columbia University, New York, USA
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Publication History

Publication Date:
20 September 2011 (online)

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Significance

Hexabenzocoronene 2 and a family of dibenzotetrathienocoronenes 6 were prepared from 6,13-pentacenequinone (1) via an efficient and high-yielding route. The route is modular, with 1,1,8,8-tetrabromobisolefin 2 serving as a common intermediate for Suzuki-Miyaura couplings with a range of boronic acids and esters. The synthesis is completed by the oxidative photocyclization of 3 and 5 with iodine and propylene oxide.