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Volumn 72, Issue 9, 2007, Pages 3289-3292

Ruthenium-catalyzed cyclization of 2-alkyl-1-ethynylbenzenes via a 1,5-hydrogen shift of ruthenium-vinylidene intermediates

Author keywords

[No Author keywords available]

Indexed keywords

1-INDANONE; CYCLIZATION MECHANISM; HYDROGEN SHIFT;

EID: 34247562660     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062573l     Document Type: Article
Times cited : (73)

References (26)
  • 2
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    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford, UK
    • Okamura, W. H.; Delera, A. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, Part 6.2, p 699.
    • (1991) Comprehensive Organic Synthesis , vol.5 , Issue.PART 6.2 , pp. 699
    • Okamura, W.H.1    Delera, A.R.2
  • 11
    • 23944457342 scopus 로고    scopus 로고
    • For the communication of this paper, see:, The content of that work will not be repeatedly reported in this full account
    • For the communication of this paper, see: Datta, S.; Odedra, A.; Liu, R.-S. J. Am. Chem. Soc. 2005, 127, 11606. The content of that work will not be repeatedly reported in this full account.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 11606
    • Datta, S.1    Odedra, A.2    Liu, R.-S.3
  • 15
    • 17344367543 scopus 로고    scopus 로고
    • For example, the 1,5-hydrogen shift proceeds rapidly for cyclopentadiene framework at ambient temperatures, but it becomes very difficult in an indene structure. See the following review: Spangler C. W. Chem. Rev. 1976, 76, 187.
    • For example, the 1,5-hydrogen shift proceeds rapidly for cyclopentadiene framework at ambient temperatures, but it becomes very difficult in an indene structure. See the following review: Spangler C. W. Chem. Rev. 1976, 76, 187.
  • 17
    • 16244409806 scopus 로고    scopus 로고
    • 6, see selected examples: (a) Lian, J.-J.; Odedra, A. Wu, C.-J.: Liu, R.-S. J. Am. Chem. Soc. 2005, 127, 4186.
    • 6, see selected examples: (a) Lian, J.-J.; Odedra, A. Wu, C.-J.: Liu, R.-S. J. Am. Chem. Soc. 2005, 127, 4186.
  • 21
    • 7244242658 scopus 로고    scopus 로고
    • 5 species to form borate and phosphate. See: (a) Krossing, I.; Raabe, I. Chem. Eur. J. 2004, 10, 5017.
    • 5 species to form borate and phosphate. See: (a) Krossing, I.; Raabe, I. Chem. Eur. J. 2004, 10, 5017.
  • 24
    • 34247567517 scopus 로고    scopus 로고
    • We propose that the ruthenium-catalyzed transformation of 1-siloxy-1H-indenes into 1-indanones presumably proceeds via a sequential 1,2-hydride shift of intermediate. The discussion of this mechanism is provided in the Supporting Information.
    • We propose that the ruthenium-catalyzed transformation of 1-siloxy-1H-indenes into 1-indanones presumably proceeds via a sequential 1,2-hydride shift of intermediate. The discussion of this mechanism is provided in the Supporting Information.
  • 25
    • 34247622458 scopus 로고    scopus 로고
    • Sames et al. recently reported a unique Lewis acid-catalyzed hydroalkylation of electron-deficient alkenes,15 indicating the feasibility of a through-space 1,5-hydride shift. We cannot exclude this mechanism because our experimental results in this work are also compatible with a through-space 1,5-hydride shift. We prefer the classical 1,5-hydrogen shift because it was reported for 2-alkyl-1-allenylbenzenes at 185 °C.9
    • 9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.