Synthesis of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide |
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| Authors: | Keita Hyodo Hikaru Nonobe Shuhei Nishinaga Yasushi Nishihara |
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| Institution: | 1. Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan;2. Japan Science and Technology Agency, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan |
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| Abstract: | Phenanthro1,2-b:8,7-b′]dithiophene (PDT) was prepared via Suzuki–Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro1,2-b:8,7-b′]dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki–Miyaura coupling of the brominated PDT with alkylboranes by introducing linear alkyl substituents. |
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| Keywords: | Phenacenes Suzuki&ndash Miyaura coupling Negishi coupling Boron Zinc |
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