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J. Jin et al.
LETTER
Acknowledgment
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2
This work was supported by 973 Program (2007CB714504) and
National Natural Science Fund for Creative Research Groups of
China (20821063).
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2
solution of the aryl chloride (0.1 mmol), Pd(OAc) (3
(
(
2
mol%), DABCO (6 mol%) and TBAB (0.1 equiv), in DMF
7
(1 mL) was prepared and taken up in a SGE gas-tight
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3
4
2
equiv), and phenylboronic acid (1.5 equiv) in H O (1 mL),
2
containing DMF (50 mL) as an added to dissolve
phenylboronic acid, was also prepared and taken up in a
second SGE gas-tight syringe. The syringes were placed on
a TS2-60 syringe pump that was set to deliver 0.9 mL/min
and the oil bath was set at 50 °C. The output from the reactor
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(
5
was quenched with Et O immediately. The resulting mixture
2
was extracted with Et O (3 × 5 mL) and the combined
(
2
organic phase was washed with brine, and dried with
(
(
b) Colacot, T. J.; Shea, H. A. Org. Lett. 2004, 6, 3731.
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anhydrous Na SO , then concentrated and the desired
2
4
product was submitted for NMR analysis. In optimization
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1
experiments, the H NMR spectrum of the product mixture
was recorded and the product conversion was determined by
integration of the peaks arising from CH or OCH groups of
3
3
both the aryl chloride and the product. The conversion was
calculated using the formula: [Int.(prod)/Int.(prod + aryl
chloride)] × 100.
2
004, 38. (f) Zapf, A.; Beller, M. Chem. Commun. 2005,
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19) Batch Reaction; Typical Procedure. A mixture of aryl
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K PO ·3H O (3 equiv), H O (5 mL) and DMF (5 mL), was
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3
4
2
2
added to a 25 mL round-bottomed flask, and stirred at 50 °C
or 80 °C for either 4 h or 24 h. After the reaction, the solution
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was cooled to room temperature and extracted with Et O
8160. (b) Liu, L. F.; Zhang, Y. H.; Wang, Y. G. J. Org.
2
(
3 × 15 mL). The combined organic phase was washed with
Chem. 2005, 70, 6122.
brine, and dried with anhydrous Na SO , then concentrated
(
(
(
10) Basheer, C.; Hussain, F. S. J.; Lee, H. K.; Valiyaveettil, S.
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2
4
1
and the product was analyzed by H NMR in order to judge
the conversion of aryl chloride. All of the final compounds
in this study were isolated by silica gel chromatography
62, 31.
(petroleum ether) for the purpose of spectroscopic
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(
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373.
Synlett 2009, No. 15, 2534–2538 © Thieme Stuttgart · New York