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Volumn 6, Issue 8, 2004, Pages 1325-1327

Rhenium-catalyzed aromatic propargylation

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BETA APOPICROPODOPHYLIN; CHEMICAL COMPOUND; FUNCTIONAL GROUP; MIMOSIFOLIOL; O METHYLDETROL; PODOPHYLLIN; RHENIUM; RHENIUM COMPLEX; TOLTERODINE; UNCLASSIFIED DRUG;

EID: 2542466672     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049649p     Document Type: Article
Times cited : (150)

References (30)
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    • Recently, catalytic amounts of rare earth triflates have been employed, (a) Kobayshi, S.; Suguira, M.; Kitagawa, H.; Lam, W. W. L. Chem. Rev. 2002, 102, 2227. (b) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780. For an organocatalytic Friedel-Crafts reaction, see: Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370.
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    • Recently, catalytic amounts of rare earth triflates have been employed, (a) Kobayshi, S.; Suguira, M.; Kitagawa, H.; Lam, W. W. L. Chem. Rev. 2002, 102, 2227. (b) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780. For an organocatalytic Friedel-Crafts reaction, see: Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 10780
    • Evans, D.A.1    Scheidt, K.A.2    Fandrick, K.R.3    Lam, H.W.4    Wu, J.5
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    • Recently, catalytic amounts of rare earth triflates have been employed, (a) Kobayshi, S.; Suguira, M.; Kitagawa, H.; Lam, W. W. L. Chem. Rev. 2002, 102, 2227. (b) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780. For an organocatalytic Friedel-Crafts reaction, see: Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370.
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    • For Ru-catalyzed propargylations, see: (a) Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 11846. (b) Nishibayashi, Y.; Inada, Y.; Yoshikawa, M.; Hidai, M.; Uemura, S. Angew. Chem., Int. Ed. 2003, 42, 1495. For propargylations involving stoichiometric amounts of transition metals, see: (c) Grove, D. D.; Corte, J. R.; Spencer, R. P.; Pauly, M. E.; Rath, N. P. J. Chem. Soc., Chem. Commun. 1994, 49. (d) Müller, T. J. J. Eur. J. Org. Chem. 2001, 2021.
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    • These substituents would be expected to result in increased cationic character at the alkynyl carbon (allenyl cation), (a) Olah, G. A.; Porter, R. D.; Kelly, D. P. J. Am. Chem. Soc. 1971, 93, 464. (b) Siehl, H.-U.; Kaufmann, F.-P. J. Am. Chem. Soc. 1992, 114, 4937.
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    • Small amount of a dimer of 15 was also isolated (see Supporting Information)
    • Small amount of a dimer of 15 was also isolated (see Supporting Information)
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    • note
    • 6b complexes affords pyran 8, while our rhenium-catalyzed reaction exclusively produces propargyl adduct 7b (Scheme 3). This suggests that the reactions are proceeding through different mechanisms or nucleophilic attack on different electrophilic intermediates.


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