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Volumn 11, Issue 10, 2009, Pages 1576-1580

A new homogeneous polymer support based on syndiotactic polystyrene and its application in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions

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EID: 70350043747     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b913060h     Document Type: Article
Times cited : (39)

References (52)
  • 23
    • 9344225112 scopus 로고    scopus 로고
    • There have been reports on the recovery yield of soluble polymer supports. See, for example
    • There have been reports on the recovery yield of soluble polymer supports. See, for example: K. C. Y. Lau H. S. He P. Chiu P. H. Toy J. Comb. Chem. 2004 6 955.
    • (2004) J. Comb. Chem. , vol.6 , pp. 955
    • Lau, K.C.Y.1    He, H.S.2    Chiu, P.3    Toy, P.H.4
  • 48
    • 85032774568 scopus 로고    scopus 로고
    • See Electronic Supplementary Information for detailed procedures for the alternative recycling experiment
    • See Electronic Supplementary Information for detailed procedures for the alternative recycling experiment.
  • 49
    • 0035356045 scopus 로고    scopus 로고
    • It appears that the sPS–TPP–Pd complex was gradually deactivated over the course of recycling work-up procedure (i.e., precipitation of the polymer support with methanol and washing with water to remove the base). The total amount of palladium leached out during the recycling was not significant; 0.023 mol% (2.3% × 1 mol%) over the five cycles. Thus, the loss of palladium due to leaching will not be a major culprit that causes the loss of catalytic activity. A similar deactivation of palladium-phosphine complex supported on cross-linked polystyrene has been reported. See
    • It appears that the sPS–TPP–Pd complex was gradually deactivated over the course of recycling work-up procedure (i.e., precipitation of the polymer support with methanol and washing with water to remove the base). The total amount of palladium leached out during the recycling was not significant; 0.023 mol% (2.3% × 1 mol%) over the five cycles. Thus, the loss of palladium due to leaching will not be a major culprit that causes the loss of catalytic activity. A similar deactivation of palladium-phosphine complex supported on cross-linked polystyrene has been reported. See C. A. Parrish S. L. Buchwald J. Org. Chem. 2001 66 3820.
    • (2001) J. Org. Chem. , vol.66 , pp. 3820
    • Parrish, C.A.1    Buchwald, S.L.2
  • 50
    • 85032776769 scopus 로고    scopus 로고
    • the ICP-AES experiment, we also discovered that the synthesized sPS–TPP contained a small quantity of palladium (0.37 wt%) possibly due to the coordination of palladium to the phosphine during sPS–TPP synthesis. However, the 1 mol% sPS–TPP alone, although it contains 0.045 mol% of residual palladium, could not catalyze Suzuki–Miyaura coupling reactions of aryl bromide even at 110 °C and only starting materials were observed
    • In the ICP-AES experiment, we also discovered that the synthesized sPS–TPP contained a small quantity of palladium (0.37 wt%) possibly due to the coordination of palladium to the phosphine during sPS–TPP synthesis. However, the 1 mol% sPS–TPP alone, although it contains 0.045 mol% of residual palladium, could not catalyze Suzuki–Miyaura coupling reactions of aryl bromide even at 110 °C and only starting materials were observed.


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