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Volumn , Issue 1, 2004, Pages 177-181

Synthesis of Functionalized Carbon-Sulfur [5]Helicene: Pd-Catalyzed Negishi Cross-Coupling between the β-Positions of Thiophenes

Author keywords

Alkylthiophene; Cross coupling; Helical structures; Helicene; Oligothiophene

Indexed keywords

ALKENE DERIVATIVE; CARBON; PALLADIUM; SULFUR; THIOPHENE DERIVATIVE;

EID: 0346970750     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43335     Document Type: Article
Times cited : (24)

References (54)
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    • Thiophene-based helicenes: (a) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899. (b) Yamada, K.; Kobori, Y.; Nakagawa, H. Chem. Commun. 2000, 97. (c) Tanaka, K.; Osuga, H.; Suzuki, H.; Shogase, Y.; Kitahara, Y. J. Chem. Soc., Perkin Trans. 1 1998, 935. (d) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 61, 1151. (e) Yamada, K.; Ogashiwa, S.; Tanaka, H.; Nakagawa, H.; Kawazura, H. Org. Lett. 1981, 343. (f) Wynberg, H. Acc. Chem. Res. 1971, 4, 65.
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    • Thiophene-based helicenes: (a) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899. (b) Yamada, K.; Kobori, Y.; Nakagawa, H. Chem. Commun. 2000, 97. (c) Tanaka, K.; Osuga, H.; Suzuki, H.; Shogase, Y.; Kitahara, Y. J. Chem. Soc., Perkin Trans. 1 1998, 935. (d) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 61, 1151. (e) Yamada, K.; Ogashiwa, S.; Tanaka, H.; Nakagawa, H.; Kawazura, H. Org. Lett. 1981, 343. (f) Wynberg, H. Acc. Chem. Res. 1971, 4, 65.
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    • note
    • Attempts at direct alkylation of a-metallated 4 with 1-bromooctane resulted in either negligible extent of conversion and/or migration of the TMS group with alkylation at the a-position adjacent to the bromine.
  • 41
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    • 2-Octylthiophene may also be prepared by reaction of iodine with ate complexes of trioctylborane and 2-thienyllithium: Sotoyama, T.; Hara, S.; Suzuki, A. Bull. Chem. Soc. Jpn. 1979, 52, 1865.
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    • note
    • 2O.
  • 46
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    • note
    • 1H resonance at δ = 7. 231 ppm appears as a broadened triplet (a singlet with two shoulders).
  • 47
    • 0346164221 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of crude mixtures, are in the 40-50% range.
  • 48
    • 0346794751 scopus 로고    scopus 로고
    • note
    • (a) Allylic coupling of J = 1 Hz is also observed in thiophenes 6 and 7. (b) The downfield shift for the β-proton in dilithiated 14 relative to the monolithiated 14 is found as well (Figure 2).
  • 49
    • 0346794752 scopus 로고    scopus 로고
    • note
    • The center part of the multiplet is somewhat broadened.
  • 53
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    • note
    • (a) 3,3′-Bithianaphthenyl 19: mp 82-83°C (lit mp 82.7-83.0 °C).
  • 54
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    • these authors report 72% yield of 'pink solid' of 19, prior to column chromatography and recrystallization
    • (b) Wynberg, H.; Cabell, M. J. Org. Chem. 1973, 38, 2814; these authors report 72% yield of 'pink solid' of 19, prior to column chromatography and recrystallization.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.