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Volumn 71, Issue 10, 2006, Pages 3748-3753

Synthesis of indoles by intermolecular cyclization of unfunctionalized nitroarenes and alkynes, catalyzed by palladium-phenanthroline complexes

Author keywords

[No Author keywords available]

Indexed keywords

3-ARYLINDOLES; ELECTRON-WITHDRAWING SUBSTITUENTS; ISOTOPE EFFECT; PALLADIUM-PHENANTHROLINE COMPLEXES;

EID: 33646507094     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060073m     Document Type: Article
Times cited : (71)

References (36)
  • 1
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press: London
    • Sundberg, R. J. Indoles; Academic Press: London, 1996.
    • (1996) Indoles
    • Sundberg, R.J.1
  • 8
    • 30744441655 scopus 로고    scopus 로고
    • Just before submission of this paper, the same authors have reported the extension of the reaction based on the use of the nitrosoarenes to the synthesis of N-methoxyindoles: Penoni, A.; Palmisano, G.; Broggini, G.; Kadowaki, A.; Nicholas, K. M. J. Org. Chem. 2006, 71, 823-825.
    • (2006) J. Org. Chem. , vol.71 , pp. 823-825
    • Penoni, A.1    Palmisano, G.2    Broggini, G.3    Kadowaki, A.4    Nicholas, K.M.5
  • 17
    • 33646500827 scopus 로고    scopus 로고
    • note
    • The lower selectivity may be due to the availability of only one ortho position on the nitroarene, but the lower conversion is likely due to a more difficult reduction of the nitroarene, which appears to be the slow step of the reaction (see also later). Due to the low yield of this indole, it could not be isolated in a pure form, and the identification of 3jb is to be considered only as a proposal.
  • 21
    • 33646504156 scopus 로고    scopus 로고
    • note
    • 2 would consume only 0.66% of the starting nitroarene, making it impossible to detect its consumption.
  • 24
    • 33646502405 scopus 로고    scopus 로고
    • note
    • f values in a chromatographic separation. An analytically pure sample of 3cm could not be obtained, and accordingly, this compound is not mentioned in the tables or in the Experimental Section.
  • 27
    • 33646510904 scopus 로고    scopus 로고
    • note
    • 28
  • 29
    • 33646497680 scopus 로고    scopus 로고
    • note
    • 30 However, this difference is to be expected because Gladefter's study was conducted at 25 °C, whereas our reactions were performed at 170 °C. Because the nitroarene reduction becomes easier at higher temperatures, both ΔG and AAG values for different nitroarenes will decrease. This will accordingly affect the differences in rate constants and result in a lower slope in the Hammett plot.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.