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Volumn 8, Issue 3, 2006, Pages 375-378

Practical preparation method of polymer-incarcerated (PI) palladium catalysts using Pd(II) salts

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EID: 32644431645     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052310y     Document Type: Article
Times cited : (74)

References (49)
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    • Recently, immobilized Pd catalysts using effective dendrimers, multilayer polyelectrolyte films, and ionic liquids have been reported. (a) Ooe, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2004, 126, 1604.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 1604
    • Ooe, M.1    Murata, M.2    Mizugaki, T.3    Ebitani, K.4    Kaneda, K.5
  • 22
    • 32644448198 scopus 로고    scopus 로고
    • note
    • It was observed by transmission electron microscope (TEM) analysis that the size of immobilized palladium particles was less than 1.5 nm and Pd dispersed uniformly on the polymer.
  • 23
    • 32644441700 scopus 로고    scopus 로고
    • note
    • Immobilization of Pd nanoparticles in the presence of tetrabutylammonium bromide (1 equiv) was also effective [yield 206 mg, 0.45 mmol/g (70%)]. However, reactivity of this catalyst in Heck reaction of iodobenzene and ethyl acrylate was low (49% yield).
  • 24
    • 32644443331 scopus 로고    scopus 로고
    • note
    • This observation suggested that formation of Pd(0) from Pd(II) and subsequent stabilization by the polymer might be the key to the success of the current immobilization method.
  • 25
    • 0003143466 scopus 로고    scopus 로고
    • Feldheim, D. L., Foss, C. A., Jr., Eds.; Marcel Dekker: New York; Chapter 2
    • It has been reported that ionic compounds such as those containing halides, carboxylates, or polyoxoanions might form an electrical double layer around the metal particles to suppress aggregation of metals. (a) Finke R. G. In Metal Nanoparticles: Synthesis, Characterization and Application; Feldheim, D. L., Foss, C. A., Jr., Eds.; Marcel Dekker: New York, 2002; Chapter 2, pp 17-54.
    • (2002) Metal Nanoparticles: Synthesis, Characterization and Application , pp. 17-54
    • Finke, R.G.1
  • 29
    • 3042797209 scopus 로고    scopus 로고
    • 4 suggested the effect of phosphine ligands as stabilizers as well. Synthesis of Pd nonoparticles stabilized by phosphine ligands has recently been reported; see: (a) Son, S. U.; Jang, Y.; Yoon, K. Y.; Kang, E.; Hyeon, T. Nano Lett. 2004, 4, 1147.
    • (2004) Nano Lett. , vol.4 , pp. 1147
    • Son, S.U.1    Jang, Y.2    Yoon, K.Y.3    Kang, E.4    Hyeon, T.5
  • 33
    • 32644442401 scopus 로고    scopus 로고
    • note
    • Transmission electron microscope (TEM) analysis showed that the size of Pd particles of PI Pd G and H are 3-5 nm.
  • 35
    • 0000633011 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (b) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 833-863.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 833-863
    • Heck, R.F.1
  • 38
    • 32644439641 scopus 로고    scopus 로고
    • note
    • Aggregation of the Pd cluster was observed after the first use (entries 2 and 3). However, no further aggregation was confirmed after the second and the third use. Partial loss of the catalytic activity after the first use might be attributed to this aggregation. PI Pd H also showed the same tendancy as PI Pd B (see Supporting Inforamtion).
  • 41
    • 0001786881 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany
    • (c) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; p 49.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 49
    • Suzuki, A.1
  • 42
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    • Schlosser, M., Ed.; Miley: West Sussex, U.K.
    • (d) Organometallics in Synthesis: A Manual; Schlosser, M., Ed.; Miley: West Sussex, U.K., 1995.
    • (1995) Organometallics in Synthesis: A Manual
  • 48
    • 1842733481 scopus 로고    scopus 로고
    • Recently, biphastic Suzuki-Miyaura coupling of aryl chlorides using MeOPEG-supported palladium phosphine complexes was reported, see: Heiden, M. A. D.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
    • (2004) Chem. Eur. J. , vol.10 , pp. 1789
    • Heiden, M.A.D.1    Plenio, H.2
  • 49
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    • note
    • When tris(o-methoxyphenyl)phosphine ligand was used, product was obtained in 17% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.