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Molecules 2016, 21(9), 1205;

A Highly Efficient and Reusable Palladium(II)/Cationic 2,2’-Bipyridyl-Catalyzed Stille Coupling in Water

Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 10608, Taiwan
Author to whom correspondence should be addressed.
Academic Editors: Diego A. Alonso and Isidro M. Pastor
Received: 13 August 2016 / Revised: 2 September 2016 / Accepted: 6 September 2016 / Published: 9 September 2016
(This article belongs to the Special Issue Palladium Catalysts 2016)
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A water-soluble PdCl2(NH3)2/cationic 2,2′-bipyridyl system was found to be a highly efficient catalyst for Stille coupling of aryl iodides and bromides with organostannanes. The coupling reaction was conducted at 110 °C in water, under aerobic conditions, in the presence of NaHCO3 as a base to afford corresponding Stille coupling products in good to high yields. When aryltributylstannanes were employed, the reactions proceeded smoothly under a very low catalyst loading (as little as 0.0001 mol %). After simple extraction, the residual aqueous phase could be reused in subsequent runs, making this Stille coupling economical. In the case of tetramethylstannane, however, a greater catalyst loading (1 mol %) and the use of tetraethylammonium iodide as a phase-transfer agent were required in order to obtain satisfactory yields. View Full-Text
Keywords: stille coupling; water-soluble catalyst; reusable; aryl halides; organostannane stille coupling; water-soluble catalyst; reusable; aryl halides; organostannane

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Wu, W.-Y.; Liu, L.-J.; Chang, F.-P.; Cheng, Y.-L.; Tsai, F.-Y. A Highly Efficient and Reusable Palladium(II)/Cationic 2,2’-Bipyridyl-Catalyzed Stille Coupling in Water. Molecules 2016, 21, 1205.

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