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Volumn , Issue 13, 2007, Pages 2053-2056

A simple and versatile synthesis of 1,2-diarylacenaphthylenes via Suzuki-Miyaura coupling, and its application in the synthesis of a new acenaphthylene-1,2-bis(p-quinone methide) derivative

Author keywords

Arenes; Chromophores; Cross coupling; Quinines; Suzuki reaction

Indexed keywords

1,2 DIARYLACENAPHTHYLENE; ACENAPHTHYLENE; ACENAPHTHYLENE 1,2 BIS (1,4 QUINONE METHIDE); QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34548160714     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984897     Document Type: Article
Times cited : (15)

References (28)
  • 19
    • 20444454604 scopus 로고    scopus 로고
    • Nickel and platinum complexes of 4 have been reported: Begum, R. A.; Sharp, P. R. Organometallics 2005, 24, 2670.
    • Nickel and platinum complexes of 4 have been reported: Begum, R. A.; Sharp, P. R. Organometallics 2005, 24, 2670.
  • 20
    • 34548149452 scopus 로고    scopus 로고
    • Recently, Dyker et al. reported a Heck-type reaction of a parent acenaphthylene with 1-bromonaphthalene to afford a bisnaphthylated product in 19% yield: Dyker, G.; Merz, K.; Oppel, I. M.; Muth, E. Synlett 2007, 897.
    • Recently, Dyker et al. reported a Heck-type reaction of a parent acenaphthylene with 1-bromonaphthalene to afford a bisnaphthylated product in 19% yield: Dyker, G.; Merz, K.; Oppel, I. M.; Muth, E. Synlett 2007, 897.
  • 22
    • 34548157959 scopus 로고    scopus 로고
    • In agreement with literature reports,3c,7 1H NMR spectra of 1e and 1f show the presence of 1:1 mixtures of rotational isomers
    • 1H NMR spectra of 1e and 1f show the presence of 1:1 mixtures of rotational isomers.
  • 23
    • 0028029627 scopus 로고    scopus 로고
    • 3): δ = 8.10 (s, 6 H), 5.59 (s, 3 H), 1.53 (s, 54 H). The trimethylsilyl-protected derivative of 5 was synthesized by Satoh et al.: Satoh, Y.; Shi, C. Synthesis 1994, 1146.
    • 3): δ = 8.10 (s, 6 H), 5.59 (s, 3 H), 1.53 (s, 54 H). The trimethylsilyl-protected derivative of 5 was synthesized by Satoh et al.: Satoh, Y.; Shi, C. Synthesis 1994, 1146.
  • 25
    • 34548147458 scopus 로고    scopus 로고
    • Crystallographic data of 3: C40H46O 2, M, 558.80, monoclinic, P2/c, a, 21.040 (9, b, 13.717 (6, c, 24.053 (10) Å, β, 103.24 (4)°, V, 6757 (17) Å3, Z, 8, D c, 1.098 g cm-3, 64264 reflections measured, 15373 unique (Rint, 0.145) used in refinement. R1, 0.058 [I > 2σ(I, wR, 0.155 (all data, T, 200 K. X-ray data have been deposited at the Cambridge Crystallographic Data Centre (CCDC-649872, Copies of the data can be obtained free of charge at www.ccdc.cam.uk/data_request/cif or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk
    • int = 0.145) used in refinement. R1 = 0.058 [I > 2σ(I)], wR = 0.155 (all data). T = 200 K. X-ray data have been deposited at the Cambridge Crystallographic Data Centre (CCDC-649872). Copies of the data can be obtained free of charge at www.ccdc.cam.uk/data_request/cif or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk].
  • 26
    • 34548185902 scopus 로고    scopus 로고
    • 5 solution. The coalescence temperature of the tert-butyl signals was 78 ± 3°C
    • 5 solution. The coalescence temperature of the tert-butyl signals was 78 ± 3°C
  • 27
    • 34548152736 scopus 로고    scopus 로고
    • Measurements were carried out in DMF solution at r.t. using a glassy carbon electrode with tetrabutylammonium perchlorate as the supporting electrolyte
    • Measurements were carried out in DMF solution at r.t. using a glassy carbon electrode with tetrabutylammonium perchlorate as the supporting electrolyte.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.