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Volumn 127, Issue 44, 2005, Pages 15354-15355

Regio- and stereoselective homocoupling of γ-arylated tert-propargyl alcohols with liberation of a ketone molecule and successive cyclization to produce fluorescent dihydrofuran derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKYNE; CARBON; DIHYDROFURAN; FURAN DERIVATIVE; KETONE; LIGAND; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

EID: 27644584950     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055452w     Document Type: Article
Times cited : (95)

References (39)
  • 25
    • 27644472986 scopus 로고    scopus 로고
    • note
    • 2-sp bonds is known. The reaction may proceed via either in situ generation of terminal alkynes or β-carbon elimination; see refs 4a,b and the relevant literature cited therein.
  • 26
    • 27644563378 scopus 로고    scopus 로고
    • note
    • 2 is considered to be due to its better ability to form the alkoxy complex. This resembles transmetalation with arylboronic acids.
  • 29
    • 27644541731 scopus 로고    scopus 로고
    • note
    • 2O or via H-D exchange of the starting alcohol.
  • 30
    • 27644558053 scopus 로고    scopus 로고
    • note
    • The reaction occurred only to a minor extent to give 10% of 2ap and completely stopped within 1 h. No cross-coupling with the terminal alkyne as well as its homocoupling was observed. However, the origin of the inhibiting effect is not clear at the present stage.
  • 33
    • 27644511138 scopus 로고
    • Of the expected cyclization products, only 3ap is known. Interestingly, it was described that the furan afforded fluorescent yellow-green needles, while the synthesis was rather tedious: Filler, R.; Piasek, E. J.; Mark, L. H. J. Org. Chem. 1961, 26, 2659.
    • (1961) J. Org. Chem. , vol.26 , pp. 2659
    • Filler, R.1    Piasek, E.J.2    Mark, L.H.3
  • 36
    • 27644538717 scopus 로고    scopus 로고
    • note
    • -4.
  • 39
    • 27644443546 scopus 로고    scopus 로고
    • note
    • A reviewer kindly suggested an alternative possibility for the lack of fluorescence of compound 3af: efficient energy transfer to the fluorenyl moiety followed by nonradiative decay of the excited state. Thus, further studies are required to establish the detail of the structural effect.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.