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Volumn 45, Issue 22, 2006, Pages 3647-3650

AuI-catalyzed tandem [3,3] rearrangement-intramolecular hydroarylation: Mild and efficient formation of substituted indenes

Author keywords

Alkynes; Allenes; Gold; Hydroarylation; Indenes

Indexed keywords

CATALYST ACTIVITY; OLEFINS; SUBSTITUTION REACTIONS;

EID: 33746275648     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600571     Document Type: Article
Times cited : (297)

References (56)
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    • see the Supporting Information
    • For details, see the Supporting Information.
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    • note
    • Characteristic signals for the expected indene could be observed in the 1H NMR spectrum of the crude reaction mixture and accounted f or <5% of the signal intensity, but this product could not be cleanly isolated.
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    • note
    • Compounds 2h and 3h were easily separated by flash chromatography.
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    • For selected examples of intramolecular electrophilic activation of an alkyne toward aromatic substitution, see: a) B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 1996, 118, 6305-6306;
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    • Trost, B.M.1    Toste, F.D.2
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    • For an extensive study of gold-catalyzed intermolecular hydroarylation, see: M. T. Reetz, K. Sommer, Eur. J. Org. Chem. 2003, 3485-3496.
    • (2003) Eur. J. Org. Chem. , pp. 3485-3496
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    • Intramolecular hydroarylation of aryl allenes leading to indenes can be catalyzed by strongly acidic media, by metals (Al, Rh, Co), or photochemically and usually requires high temperature and/or a prolonged reaction time for a moderate chemical yield; for reviews, see: a) D. R. Taylor, Chem. Rev. 1967, 67, 317-359;
    • (1967) Chem. Rev. , vol.67 , pp. 317-359
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    • (Eds.: H. F. Schuster, G. M. Coppola), Wiley, New York
    • b) Allenes in Organic Synthesis (Eds.: H. F. Schuster, G. M. Coppola), Wiley, New York, 1984;
    • (1984) Allenes in Organic Synthesis
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    • (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim
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    • (2004) Modern Allene Chemistry
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    • Cyclization occuring through C-H activation and arene auration cannot at this time be ruled out (see scheme below); for examples of arene gold(III) complexes involved in catalytic transformations, see: Z. Shi, C. He, J. Am. Chem. Soc. 2004, 126, 13596-13597. (Chemical Equation Presented)
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    • Shi, Z.1    He, C.2
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    • note
    • An alternate explanation would imply that the reaction might not go through a discrete allene intermediate; hence, a concerted mechanism would be worth consideration.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.