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Volumn 77, Issue 22, 2012, Pages 9979-9988

Palladium-catalyzed annulation of 2,2′-diiodobiphenyls with alkynes: Synthesis and applications of phenanthrenes

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM-CATALYZED; PICTET-SPENGLER REACTIONS; PYRROLIDINES;

EID: 84869176199     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302013x     Document Type: Article
Times cited : (46)

References (118)
  • 8
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    • Manske, R. H. F. Academic: New York
    • Snieckus, V. In The Alkaloids; Manske, R. H. F., Ed.; Academic: New York, 1973; Vol. 14, p 425.
    • (1973) The Alkaloids , vol.14 , pp. 425
    • Snieckus, V.1
  • 35
    • 0000075617 scopus 로고
    • Rodrigo, R. G. A. Academic: New York
    • Bick, I. R. C.; Sinchai, W. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic: New York, 1981; Vol. 19, p 193.
    • (1981) The Alkaloids , vol.19 , pp. 193
    • Bick, I.R.C.1    Sinchai, W.2
  • 83
    • 53849118099 scopus 로고    scopus 로고
    • Our earlier study indicated that the Pd-catalyzed cycloaddition of p -xylene with two molecules of diphenylacetylene forms 5,8-dimethyl-1,2,3,4- tetraphenylnaphthalene, whereas 1,2-dimethoxybenzene and toluene strongly suspend this reaction. For details, see: Wu, Y.-T.; Huang, K.-H.; Shin, C.-C.; Wu, T.-C. Chem.-Eur. J. 2008, 14, 6697
    • (2008) Chem.-Eur. J. , vol.14 , pp. 6697
    • Wu, Y.-T.1    Huang, K.-H.2    Shin, C.-C.3    Wu, T.-C.4
  • 91
    • 37049152492 scopus 로고
    • The term "overcrowding" was first introduced by Bell and Waring to define aromatic systems, which adopt nonplanar forms to accommodate certain hydrogen atoms (e.g. hydrogen atoms at positions 4 and 5 in dibenzo[ c, g ]phenanthrene); see: Bell, F.; Waring, D. H. J. Chem. Soc. 1949, 2689
    • (1949) J. Chem. Soc. , pp. 2689
    • Bell, F.1    Waring, D.H.2
  • 93
    • 33847087228 scopus 로고
    • One reviewer suggested that the two conformers 8ei -A and 8ei -B may be indistinguishable because they have a smaller pseudorotation barrier, compared to 3,4,5,6-tetramethylphenanthrene. The effective Van der Waals radius of a methoxy group (1.51 Å) is smaller than that of a methyl group (1.80 Å), and this causes 8ei to have a lower pseudorotation barrier. For details, see: Bott, G.; Field, L. D.; Sternhell, S. J. Am. Chem. Soc. 1980, 102, 5618
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5618
    • Bott, G.1    Field, L.D.2    Sternhell, S.3
  • 100
    • 0344048366 scopus 로고    scopus 로고
    • Negishi, E.-I. de Meijere, A. Wiley: New York
    • For a review on the regioselectivity of alkyne insertion (carbopalladation of alkynes), see: Cacchi, S.; Fabrizi, G. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I.; de Meijere, A., Eds.; Wiley: New York, 2002; Vol. 2, p 1335.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.2 , pp. 1335
    • Cacchi, S.1    Fabrizi, G.2
  • 107
    • 84869170719 scopus 로고    scopus 로고
    • Faming Zhuanli Shenqing, CN 101189968 A 20080604.
    • A patent covers the preparation of alkaloid 10, but no analytic data such as NMR spectra were provided. For details, see: Wang, Q.; Wang, K.; Huang, Z.; Liu, Y.; Li, H.; Hu, T.; Jin, Z.; Fan, Z.; Huang, R. Faming Zhuanli Shenqing, 2008, CN 101189968 A 20080604.
    • (2008)
    • Wang, Q.1    Wang, K.2    Huang, Z.3    Liu, Y.4    Li, H.5    Hu, T.6    Jin, Z.7    Fan, Z.8    Huang, R.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.