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Organic Letters
Volumn 10, Issue 4, 2008, Pages 621-623
Synthesis of C5-symmetric functionalized [60]fullerenes by copper-mediated 5-fold addition of reformatsky reagents
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EID: 39749123144     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702874w     Document Type: Article
Times cited : (18)
References (33)
  • 4
    • 0004249303 scopus 로고
    • Taylor, R, Ed, World Scientific: River Edge, NJ
    • (d) The Chemistry of Fullerenes; Taylor, R., Ed.; World Scientific: River Edge, NJ, 1995.
    • (1995) The Chemistry of Fullerenes
  • 24
    • 29144530838 scopus 로고    scopus 로고
    • O'Neil, I. A, Ed, Georg Thime Verlag: Stuttgart
    • (b) Knochel, P. In Science of Synthesis; O'Neil, I. A., Ed.; Georg Thime Verlag: Stuttgart, 2004; Vol. 3, pp 5-90.
    • (2004) Science of Synthesis , vol.3 , pp. 5-90
    • Knochel, P.1
  • 26
    • 39749136688 scopus 로고    scopus 로고
    • A typical procedure for preparation of la: To a THF (10 mL) suspension of CuBr·SMe2 (308 mg, 1.50 mmol) and N,N′-dimethyl-2-imidazolidinone (0.16 mL, 1.5 mmol) was added dropwise a THF solution of BrZnCH2CO2Et (0.7 M, 2.1 mL, 1.5 mmol) at 25°C under an argon atmosphere. After the copper/zinc mixture was stirred for 10 min, a 1,2-dichlorobenzene (5 mL) solution of C60 (72 mg, 0.10 mmol) was added at once. The reaction mixture was stirred at 25°C for 4 h and then quenched with saturated aqueous ammonium chloride solution (0.1 mL, The resulting mixture was diluted with degassed toluene (10 mL) and ethyl acetate (10 mL) and quickly filtered through a pad of silica gel to remove insoluble materials. The solution was quickly concentrated under reduced pressure, and was diluted with degassed methanol (100 mL, The resulting precipitate was collected and dried in vacuo to obtain la 107 mg, 92% yield, purity
    • 60 (72 mg, 0.10 mmol) was added at once. The reaction mixture was stirred at 25°C for 4 h and then quenched with saturated aqueous ammonium chloride solution (0.1 mL). The resulting mixture was diluted with degassed toluene (10 mL) and ethyl acetate (10 mL) and quickly filtered through a pad of silica gel to remove insoluble materials. The solution was quickly concentrated under reduced pressure, and was diluted with degassed methanol (100 mL). The resulting precipitate was collected and dried in vacuo to obtain la (107 mg, 92% yield, purity 88% as determined by HPLC area).

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