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All the physical data of the three ligands were in agreement with
those reported.
4.2.2. General procedure for diaryl thioethers. A flame-dried
Schlenk test tube with a magnetic stirring bar was charged with
CuBr (14 mg, 0.1 mmol), ligand (30 mg, 0.2 mmol), K2CO3 (276 mg,
2.0 mmol), thiol (1.0 mmol), aryl halide (1.5 mmol), and DMSO
(1 mL) under N2. The mixture reacted at 80 ꢀC for 24 h, then cooled
to ambient temperature, and the resulting mixture was extracted
with ethyl acetate (3ꢂ30 mL). The combined organic layers were
dried over anhydrous sodium sulfate and concentrated under
vacuum. The residue was purified by column chromatography on
silica gel (ethyl acetate/petroleum ether) to provide the desired
product. All the physical data of the known compounds were in
agreement with those reported in the literatures.
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4.2.2.1. 2-(Phenylthio)pyridin-3-ol (3e). General procedure was
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followed. Thiolphenol (103 mL, 1.0 mmol) and 2-bromopyridin-3-ol
(261 mg, 1.5 mmol) were used to obtain the product 2-(phenyl-
thio)pyridin-3-ol (138 mg, 62% yield) as white solid. Column chro-
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(400 MHz, CDCl3)
d
8.20 (dd, J¼4.4, 1.2 Hz, 1H), 7.32–7.20 (m, 7H);
13C NMR (100 MHz, CDCl3)
d
153.5, 142.8, 141.4, 133.2, 130.1, 129.5,
127.6, 125.5, 123.1 (CDCl3, 77.2); MS (ESI, m/z) 204 [MþH]þ, 226
[MþNa]þ; HRMS (ESI) calcd for C11H9NOS (MꢃH)þ 202.0327, found
202.0319. Mp: 119.4–120.6 ꢀC.
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Acknowledgements
This work was supported by the National Natural Science
Foundation of China (Project No. 20876021) and the Program for
Changjiang Scholars and Innovative Research Team in University
(IRT0711).
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Supplementary data
Experimental procedures and characterization of the products.
This material is available free of charge via ScienceDirect. Supple-
mentary data associated with this article can be found in the online
23. Wang, H. F.; Li, Y. M.; Sun, F. F.; Feng, Y.; Jin, K.; Wang, X. N. J. Org. Chem. 2008,
73, 8639–8642.
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