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Volumn 11, Issue 12, 2005, Pages 3728-3741

Palladium(0)-catalyzed tandem cyclization of alleneues: Direct construction of tricyclic heterocycles through aromatic C-H activation

Author keywords

Allenes; C H activation; Heterocycles; Palladium; Tandem cyclization

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL ACTIVATION; HYDROGEN BONDS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; OLEFINS; PALLADIUM; POTASSIUM COMPOUNDS;

EID: 20444468561     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500050     Document Type: Article
Times cited : (57)

References (84)
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    • For related palladium-catalyzed cyclization reactions of allenynes, see: a) C. H. Oh, S. H. Jung, C. Y. Rhim, Tetrahedron Lett. 2001, 42, 8669-8671;
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    • a) A palladium(II)-catalyzed domino cyclization of allenynes in the presence of LiBr under oxygen at atmospheric pressure was recently reported: B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Eur. J. 2002, 8, 1719-1729;
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    • b) Yamamoto and co-workers reported that palladium-catalyzed carbonylative tandem cyclization of an allenene that contains an allyl acetate moiety in the presence of carbon monoxide afforded the tetracyclic product in a 22% yield, although it is only an isolated example: T. Doi, A. Yanagisawa, S. Nakanishi, K. Yamamoto, T. Takahashi, J. Org. Chem. 1996, 61, 2602-2603.
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    • note
    • As separation of 12b and 13b was extremely difficult, an almost 1:1 diastereomixture of 12b and 13b was used directly for the palladium-catalyzed cyclization without further purification. Other diastereomixtures (12a/13a and 12c/13c) were readily separated by flash column chromatography.
  • 74
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    • Although the syn-β elimination generally predominates, a base-induced anti elimination by an E2 mechanism can occur in limited cases. See, for examples: a) J. M. Takacs, E. C. Lawson, F. Clement, J. Am. Chem. Soc. 1997, 119, 5956-5957;
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    • and references therein
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    • note
    • [16b]
  • 77
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    • note
    • For example, in the reaction of allenene 10a with 2-iodoanisole (Table 1, entry 5), 14% of the β-elimination product 58 was isolated. In other cases, the yields of this type of elimination product were lower (<5%) and isolation of these compounds was difficult.
  • 84
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    • see also ref. [3c]
    • c) B. Sezen, D. Sames, J. Am. Chem. Soc. 2003, 125, 5274-5275; see also ref. [3c].
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    • Sezen, B.1    Sames, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.