Nano-phosphorylated PEG/Pd(0) catalyst for C–C coupling reactions
was washed with 50 ml dry Et2O and dried under vacuum. Bis-
(diphenylphosphorylated) PEG200 was obtained as a white solid
(2.78 g, 98%), which was stored in a capped bottle. The reagent
can be kept without any change for months. In order to deter-
mine the amount of active phosphorus content of the reagent,
DPPPEG200 was reacted with excess iodine in acetonitrile and
stirred for 1 h under reflux conditions. On the basis of titration
of unreacted iodine with an aqueous solution of sodium
thiosulfate (0.1 M), the amount of active phosphorus content
Supporting information
Supporting information may be found in the online version of
this article.
Acknowledgements
We are grateful to the Research Council of Shiraz University for
the partial support of this work.
was determined to be 2.0 mmol for 1.0 mmol PEG200.
1H NMR
References
(250 MHz, DMSO): 4.53–4.70 (m, 16H, CH2O), 7.44–7.75 (m, 20H,
aromatic); 13C NMR (62.9 MHz, DMSO): 68.3 (Ph2POCH2),
71.1 (OCH2), C6H5 group (127.9, 130.6, 130.8, 131.0); IR (KBr disk)
n (cmꢁ1) 3070(w), 2876(m), 1589(s), 1481(s), 1435(s), 1180(s),
1126(s), 1064(s), 956(m), 694(m).
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General procedure for the Heck–Mizoroki Reaction between
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with Nano-Pd(0)/DPPPEG200
.
Aryl halide (1.0 mmol ) was added to a mixture of n-butyl acrylate
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DPPPEG200 (3.8 mg, 6.0 mol%) in the absence of solvent and the
reaction mixture was magnetically stirred at 80–100ꢀC (Table 4)
and monitored by TLC until the starting material was consumed.
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by addition of cold acetonitrile (10 ml) to the mixture followed by
centrifugation. The recovered catalyst was dried under vacuum
and reused in subsequent runs. The organic phase was evapo-
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) was added to a mixture of
benzeneboronic acid (1.5 mmol), K2CO3 (2.0 mmol ), PdCl2
(1.7 mg, 1.0 mol%) and DPPPEG200 (18 mg, 3.0 mol%) in EtOH
and the reaction mixture was magnetically stirred at 70ꢀC
and monitored by TLC until the starting materials were con-
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Appl. Organometal. Chem. 2013, 27, 451–458
Copyright © 2013 John Wiley & Sons, Ltd.
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