Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 16, Issue -, Pages 544-550Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.16.51
Keywords
C-H arylation; C-O arylation; oxidative cyclization; polycyclic aromatic hydrocarbons; ruthenium catalyst
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [2707]
- Research Program of Five-star Alliance in NJRC Mater. Dev.
- JSPS KAKENHI Grant [JP18H04271]
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An efficient synthesis of tetrabenzo[a,d,j,m]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[a, d,j, m]coronenes in short steps from readily available starting materials. Tetrabenzo[a,d,j,m]coronenes possessing two different types of substituents were obtained selectively by sequential chemoselective C-O arylation and C-H arylation. The H-1 NMR spectra of the tetrabenzo[a,d,j,m]coronene product indicated its self-assembling behavior in CDCl3.
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