TY - JOUR
T1 - Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[a,d,j,m]coronenes by selective C–H/C–O arylations of anthraquinone derivatives
AU - Terai, Seiya
AU - Sato, Yuki
AU - Kochi, Takuya
AU - Kakiuchi, Fumitoshi
N1 - Funding Information:
This work was supported, in part, by a Grant-in-Aid for Scientific Research on Innovative Areas 2707 “Middle molecule strategy” from the Ministry of Education, Culture, Sports, Science and Technology, Japan and by the Research Program of “Five-star Alliance” in “NJRC Mater. & Dev.”. T.K. is grateful for financial support provided by JSPS KAKENHI Grant Number JP18H04271 (Precisely Designed Catalysts with Customized Scaffolding).
Publisher Copyright:
© 2020 Terai et al.
PY - 2020/3/31
Y1 - 2020/3/31
N2 - An efficient synthesis of tetrabenzo[a,d,j,m]coronene derivatives having alkyl and alkoxy substituents at the 3, 6, 13, and 16-posi-tions 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. Tetra-benzo[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 1H NMR spectra of the tetrabenzo[a,d,j,m]coronene product indicated its self-assembling behavior in CDCl3
AB - An efficient synthesis of tetrabenzo[a,d,j,m]coronene derivatives having alkyl and alkoxy substituents at the 3, 6, 13, and 16-posi-tions 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. Tetra-benzo[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 1H NMR spectra of the tetrabenzo[a,d,j,m]coronene product indicated its self-assembling behavior in CDCl3
KW - C–H arylation
KW - C–O arylation
KW - Oxidative cyclization
KW - Polycyclic aromatic hydrocarbons
KW - Ruthenium catalyst
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U2 - 10.3762/bjoc.16.51
DO - 10.3762/bjoc.16.51
M3 - Article
AN - SCOPUS:85084398820
VL - 16
SP - 544
EP - 550
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -