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Volumn 125, Issue 20, 2003, Pages 6056-6057

Carbon-carbon bond formation in palladium(II)-catalyzed allylic oxidation: A novel oxidative carbocyclization of allene-substituted olefins

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLENE DERIVATIVE; ALLYL COMPOUND; CARBON; PALLADIUM; PHOSPHINE;

EID: 0037951429     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029505a     Document Type: Article
Times cited : (119)

References (33)
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    • 11c,d (a) Toyota, M.; Rudyanto, M.; Masataka, I. J. Org. Chem. 2002, 67, 3374-3386. (b) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (c) Rönn, M.; Andersson, P. G.; Bäckvall, J. E. Tetrahedron Lett. 1997, 38, 3603-3606. (d) Castaño, A. M.; Persson, B. A.; Bäckvall, J. E. Chem.-Eur. J. 1997, 3, 482-490.
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    • 11c,d (a) Toyota, M.; Rudyanto, M.; Masataka, I. J. Org. Chem. 2002, 67, 3374-3386. (b) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (c) Rönn, M.; Andersson, P. G.; Bäckvall, J. E. Tetrahedron Lett. 1997, 38, 3603-3606. (d) Castaño, A. M.; Persson, B. A.; Bäckvall, J. E. Chem.-Eur. J. 1997, 3, 482-490.
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    • 11c,d (a) Toyota, M.; Rudyanto, M.; Masataka, I. J. Org. Chem. 2002, 67, 3374-3386. (b) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494-496. (c) Rönn, M.; Andersson, P. G.; Bäckvall, J. E. Tetrahedron Lett. 1997, 38, 3603-3606. (d) Castaño, A. M.; Persson, B. A.; Bäckvall, J. E. Chem.-Eur. J. 1997, 3, 482-490.
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    • note
    • 2/BQ in refluxing toluene resulted in a complex mixture of unidentified products.
  • 25
    • 0037798564 scopus 로고    scopus 로고
    • note
    • 4 reduction of the corresponding allylic trifluoroacetate (see Supporting Information).
  • 26
    • 0038136314 scopus 로고    scopus 로고
    • note
    • Formation of the vinylidienepalladium intermediate A is believed to involve a nucleophilic attack on the palladium atom to give a carbocationic intermediate followed by elimination of a proton, rather than an oxidative allylic C-H abstraction. However, both pathways would lead to the same intermediate A.
  • 33
    • 0038813049 scopus 로고    scopus 로고
    • note
    • Compounds 1a and 6 would be able to form the same (π-allyl)palladium intermediate and should in that case both cyclize to give 2a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.