Cu-catalyzed C-H/C-O cyclization of 2,2'-binaphthol, using air as an oxidant, was developed. C-H functionalization of binaphthols occurred at the 8,8'-position to form peri-xanthenoxanthenes that exhibit high charge-carrier mobility. The reaction can tolerate a wide variety of functional groups and afforded the corresponding peri-xanthenoxanthene derivatives via an efficient procedure.
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Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[,,,]coronenes by selective C-H/C-O arylations of anthraquinone derivatives.
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Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
An efficient synthesis of tetrabenzo[,,,]coronene derivatives having alkyl and alkoxy substituents at the 3, 6, 13, and 16-positions was achieved based on the ruthenium-catalyzed coupling reactions of anthraquinone derivatives with arylboronates via C-H and C-O bond cleavage. The reaction sequence involving the arylation, carbonyl methylenation, and oxidative cyclization effectively provided various tetrabenzo[,,,]coronenes in short steps from readily available starting materials. Tetrabenzo[,,,]coronenes possessing two different types of substituents were obtained selectively by sequential chemoselective C-O arylation and C-H arylation.
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Key Laboratory of Renewable Energy, CAS, Guangdong Key Laboratory of New and Renewable Energy Research and Development, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, People's Republic of China.
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Org Lett
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Department of Chemical Engineering, Nara National College of Technology, 22 Yata-cho, Yamatokoriyama, Nara 639-1080, Japan.
Cu-catalyzed C-H/C-O cyclization of 2,2'-binaphthol, using air as an oxidant, was developed. C-H functionalization of binaphthols occurred at the 8,8'-position to form peri-xanthenoxanthenes that exhibit high charge-carrier mobility. The reaction can tolerate a wide variety of functional groups and afforded the corresponding peri-xanthenoxanthene derivatives via an efficient procedure.
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