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Volumn 38, Issue 37, 1997, Pages 6581-6584

Palladium complexes supported on hybrid organic-inorganic zirconium phosphite: Selectivity in the Heck reaction

Author keywords

[No Author keywords available]

Indexed keywords

IODOBENZENE; IODOBENZOIC ACID DERIVATIVE; PALLADIUM COMPLEX; ZIRCONIUM DERIVATIVE;

EID: 0343765718     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01505-0     Document Type: Article
Times cited : (50)

References (26)
  • 1
    • 0003829079 scopus 로고
    • Academic Press, London
    • Lazlo, P. (ed), 'Preparative Chemistry Using Supported Reagents', Academic Press, London, 1987 ; Smith, K. 'Solid Supports and Catalysts in Organic Synthesis'. Elis Horwood, Chichester, 1992.
    • (1987) Preparative Chemistry Using Supported Reagents
    • Lazlo, P.1
  • 3
    • 0030485144 scopus 로고    scopus 로고
    • Bone, S.; Evans, D.G.; Perriam, J.L; Slade, R.C.T., Angew. Chem. Int. Ed. Engl., 1996, 35, 1850-1852; Lane, R.H.; Callahan, K.P.; Cooksey, R.; Dines, P.M.; Griffith, P.C. Prepr. Am. Chem. Soc., Div. Pet. Chem., 1982, 27, 624-631 (C.A., 101: 130760n) ; Dines, M.B.; DiGiacomo, P.M.; Callahan, K.P. US Pat. 4,384,981, (1981) (C.A., 99: 121445b) ; Callahan, K.P.; Dines, M.B. US Pat. 4,983,564 (1984) (C.A., 115: 51412m)
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1850-1852
    • Bone, S.1    Evans, D.G.2    Perriam, J.L.3    Slade, R.C.T.4
  • 4
    • 0020179432 scopus 로고
    • C.A., 101: 130760n
    • Bone, S.; Evans, D.G.; Perriam, J.L; Slade, R.C.T., Angew. Chem. Int. Ed. Engl., 1996, 35, 1850-1852; Lane, R.H.; Callahan, K.P.; Cooksey, R.; Dines, P.M.; Griffith, P.C. Prepr. Am. Chem. Soc., Div. Pet. Chem., 1982, 27, 624-631 (C.A., 101: 130760n) ; Dines, M.B.; DiGiacomo, P.M.; Callahan, K.P. US Pat. 4,384,981, (1981) (C.A., 99: 121445b) ; Callahan, K.P.; Dines, M.B. US Pat. 4,983,564 (1984) (C.A., 115: 51412m)
    • (1982) Prepr. Am. Chem. Soc., Div. Pet. Chem. , vol.27 , pp. 624-631
    • Lane, R.H.1    Callahan, K.P.2    Cooksey, R.3    Dines, P.M.4    Griffith, P.C.5
  • 5
    • 0343555739 scopus 로고    scopus 로고
    • US Pat. 4,384,981, (1981) (C.A., 99: 121445b)
    • Bone, S.; Evans, D.G.; Perriam, J.L; Slade, R.C.T., Angew. Chem. Int. Ed. Engl., 1996, 35, 1850-1852; Lane, R.H.; Callahan, K.P.; Cooksey, R.; Dines, P.M.; Griffith, P.C. Prepr. Am. Chem. Soc., Div. Pet. Chem., 1982, 27, 624-631 (C.A., 101: 130760n) ; Dines, M.B.; DiGiacomo, P.M.; Callahan, K.P. US Pat. 4,384,981, (1981) (C.A., 99: 121445b) ; Callahan, K.P.; Dines, M.B. US Pat. 4,983,564 (1984) (C.A., 115: 51412m)
    • Dines, M.B.1    DiGiacomo, P.M.2    Callahan, K.P.3
  • 6
    • 0342685527 scopus 로고    scopus 로고
    • US Pat. 4,983,564 (1984) (C.A., 115: 51412m)
    • Bone, S.; Evans, D.G.; Perriam, J.L; Slade, R.C.T., Angew. Chem. Int. Ed. Engl., 1996, 35, 1850-1852; Lane, R.H.; Callahan, K.P.; Cooksey, R.; Dines, P.M.; Griffith, P.C. Prepr. Am. Chem. Soc., Div. Pet. Chem., 1982, 27, 624-631 (C.A., 101: 130760n) ; Dines, M.B.; DiGiacomo, P.M.; Callahan, K.P. US Pat. 4,384,981, (1981) (C.A., 99: 121445b) ; Callahan, K.P.; Dines, M.B. US Pat. 4,983,564 (1984) (C.A., 115: 51412m)
    • Callahan, K.P.1    Dines, M.B.2
  • 11
    • 0001412847 scopus 로고
    • Under argon atmosphere, dichlorobis(triphenylphosphine)palladium (0.17 mmol), triethylsilane (0.17 mmol) and 2 ml of toluene were refluxed for 5 min. in order to reduce palladium (II) complex to palladium (0). Phosphine 1 (3.45 mmol), diethylphosphite (3.47 mmol) and triethylamine (3.5 mmol) in solution of toluene (6 mL) of toluene were added. The solution was refluxed for 22 hours, washed and purified by column chromatography to offer the phosphonate 2 with 56 % yield
    • Hirao, T.; Masunaga, T.; Yamada, N. Y. Ohshiro, N.Y.; Agawa, T. Bull. Chem. Soc. Jpn., 1982, 55, 909-913. Under argon atmosphere, dichlorobis(triphenylphosphine)palladium (0.17 mmol), triethylsilane (0.17 mmol) and 2 ml of toluene were refluxed for 5 min. in order to reduce palladium (II) complex to palladium (0). Phosphine 1 (3.45 mmol), diethylphosphite (3.47 mmol) and triethylamine (3.5 mmol) in solution of toluene (6 mL) of toluene were added. The solution was refluxed for 22 hours, washed and purified by column chromatography to offer the phosphonate 2 with 56 % yield.
    • (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 909-913
    • Hirao, T.1    Masunaga, T.2    Yamada, N.Y.3    Ohshiro, N.Y.4    Agawa, T.5
  • 13
    • 0343991840 scopus 로고
    • To a solution of phosphonic acid 3 in 100 mL of DMF under argon atmosphere, we added palladium dichloride (4.7 mmol) and the solution was stirred for 24 h. Evaporation of the solvent under vacuum afforded the palladium complex 4 as a polymeric form in 98% yield ; Roffia, P.; Conti, F.; Gregori, G. Chem. Ind. (Milan), 1971, 53, 361-362.
    • (1971) Chem. Ind. (Milan) , vol.53 , pp. 361-362
    • Roffia, P.1    Conti, F.2    Gregori, G.3
  • 15
    • 0342685525 scopus 로고    scopus 로고
    • note
    • In a typical experiment, the palladium complex 4 (1.25 mmol) and phosphorous acid (15 mmol) were dissolved, under argon, in 110 ml of HCl 4.3 M. A solution of zirconium chloride octahydrated (8.3 mmol) in 15 ml of water was added dropwise. The resulting suspension was heated for 3 days. The precipitate was filtered off, washed with water to afford, after air drying, 3.25 g of orange solid ( 5).
  • 17
    • 0342685524 scopus 로고    scopus 로고
    • note
    • Found. % : H : 1.4 ; Cl : 4.46 ; P : 19.55, Zr : 27.12 ; Pd : 3.38 ; C : 10.27
  • 19
    • 0343991838 scopus 로고    scopus 로고
    • note
    • The catalyst 5 (20 mg), triethylsilane (0.01 ml) and toluene (1 ml) are placed under argon in a Schlenk tube. The solution was refluxed for 30 min. in order to reduce the palladium (II) complex to palladium (O). lodobenzene (1 mmol), methyl acrylate (0.13 ml, 1.5 eq.) and triethylamine (0.21 ml, 1.5 eq.) in 2 ml of toluene were then added and the reflux was continued for 24 h. After hydrolysis and purification by column chromatography, the methyl cinnamate was isolated with 92 % yield.
  • 20
    • 0021366619 scopus 로고
    • Csicsery, S.M. Zeolites , 1984, 4, 202-213 ; Csicsery, S.M. Pure Appl. Chem., 1986, 58, 841-856; Chen, N.Y.; Garwood, W.E. Cat. Rev. Sc. Eng., 1986, 28, 185-264; Y. Sugi Y.; Toba, M. Cat. Today, 1994, 19, 187-212.
    • (1984) Zeolites , vol.4 , pp. 202-213
    • Csicsery, S.M.1
  • 21
    • 0022736497 scopus 로고
    • Csicsery, S.M. Zeolites , 1984, 4, 202-213 ; Csicsery, S.M. Pure Appl. Chem., 1986, 58, 841-856; Chen, N.Y.; Garwood, W.E. Cat. Rev. Sc. Eng., 1986, 28, 185-264; Y. Sugi Y.; Toba, M. Cat. Today, 1994, 19, 187-212.
    • (1986) Pure Appl. Chem. , vol.58 , pp. 841-856
    • Csicsery, S.M.1
  • 22
    • 0022735884 scopus 로고
    • Csicsery, S.M. Zeolites , 1984, 4, 202-213 ; Csicsery, S.M. Pure Appl. Chem., 1986, 58, 841-856; Chen, N.Y.; Garwood, W.E. Cat. Rev. Sc. Eng., 1986, 28, 185-264; Y. Sugi Y.; Toba, M. Cat. Today, 1994, 19, 187-212.
    • (1986) Cat. Rev. Sc. Eng. , vol.28 , pp. 185-264
    • Chen, N.Y.1    Garwood, W.E.2
  • 23
    • 0028768974 scopus 로고
    • Csicsery, S.M. Zeolites , 1984, 4, 202-213 ; Csicsery, S.M. Pure Appl. Chem., 1986, 58, 841-856; Chen, N.Y.; Garwood, W.E. Cat. Rev. Sc. Eng., 1986, 28, 185-264; Y. Sugi Y.; Toba, M. Cat. Today, 1994, 19, 187-212.
    • (1994) Cat. Today , vol.19 , pp. 187-212
    • Sugi, Y.1    Toba, M.2
  • 26
    • 0007108145 scopus 로고    scopus 로고
    • Oxford Molecular Group Inc.
    • CAChe Scientific, Oxford Molecular Group Inc.
    • CAChe Scientific


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.