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Volumn 3, Issue 23, 2001, Pages 3611-3614

A novel palladium-catalyzed synthesis of phenanthrenes from ortho-substituted aryl iodides and diphenyl-or alkylphenylacetylenes

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ARTICLE;

EID: 0000831302     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016360o     Document Type: Article
Times cited : (158)

References (38)
  • 1
    • 0001538227 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • Tamao, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 3, pp 435-480.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 435-480
    • Tamao, K.1
  • 21
    • 0041726824 scopus 로고    scopus 로고
    • note
    • 2c and 10 (R = n-Bu) are present in 3% and 6%, respectively. Flash chromatography on silica with hexane as the eluent affords pure 1,5-di-n-buty1-9,10-diphenylphenanthrene 2 (R = n-Bu, 134 mg) in 84% yield as a white solid (mp 79-80°C).
  • 22
    • 0041726825 scopus 로고    scopus 로고
    • note
    • 4b to be very effective in the annulation reaction of o-iodobiphenyl with diphenylacetylene.
  • 23
    • 0043229335 scopus 로고    scopus 로고
    • note
    • 13C NMR) are in agreement with structures 3 and 4.
  • 25
    • 0002521519 scopus 로고
    • and references therein
    • For palladium(IV) chemistry, see: (a) Canty, A. J. Acc. Chem. Res. 1992, 25, 83 and references therein.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 83
    • Canty, A.J.1
  • 31
    • 0042728030 scopus 로고    scopus 로고
    • note
    • 9c).
  • 35
    • 0141492902 scopus 로고
    • Bocelli, G.; Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1985, 279, 225. Markies, B. A.; Wijkens, P.; Kooijman, H.; Spek, A. L.; Boersma, J.; van Koten, G. J. Chem. Soc., Chem. Commun. 1992, 1420. Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
    • (1985) J. Organomet. Chem. , vol.279 , pp. 225
    • Bocelli, G.1    Catellani, M.2    Chiusoli, G.P.3
  • 37
    • 0034715487 scopus 로고    scopus 로고
    • Bocelli, G.; Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1985, 279, 225. Markies, B. A.; Wijkens, P.; Kooijman, H.; Spek, A. L.; Boersma, J.; van Koten, G. J. Chem. Soc., Chem. Commun. 1992, 1420. Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 10464
    • Oguma, K.1    Miura, M.2    Satoh, T.3    Nomura, M.4


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