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10
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0033532839
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B. F. G. Johnson S. A. Raynor D. S. Shephard T. Mashmeyer J. M. Thomas G. Sankar S. Bromley R. Oldroyd L. Gladden M. D. Mantle Chem. Commun. 1999 1167.
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(1999)
Chem. Commun.
, pp. 1167
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Johnson, B.F.G.1
Raynor, S.A.2
Shephard, D.S.3
Mashmeyer, T.4
Thomas, J.M.5
Sankar, G.6
Bromley, S.7
Oldroyd, R.8
Gladden, L.9
Mantle, M.D.10
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23
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9344225112
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There have been reports on the recovery yield of soluble polymer supports. See, for example
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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.
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(2004)
J. Comb. Chem.
, vol.6
, pp. 955
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Lau, K.C.Y.1
He, H.S.2
Chiu, P.3
Toy, P.H.4
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45
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0033063092
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F. Sieber P. Wentworth, Jr. J. D. Toker A. D. Wentworth W. A. Metz N. N. Reed K. D. Janda J. Org. Chem. 1999 64 5188.
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(1999)
J. Org. Chem.
, vol.64
, pp. 5188
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Sieber, F.1
Wentworth, P.2
Toker, J.D.3
Wentworth, A.D.4
Metz, W.A.5
Reed, N.N.6
Janda, K.D.7
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48
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85032774568
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See Electronic Supplementary Information for detailed procedures for the alternative recycling experiment
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See Electronic Supplementary Information for detailed procedures for the alternative recycling experiment.
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49
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0035356045
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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
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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.
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(2001)
J. Org. Chem.
, vol.66
, pp. 3820
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Parrish, C.A.1
Buchwald, S.L.2
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50
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85032776769
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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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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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