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Molecules 2016, 21(9), 1205; doi:10.3390/molecules21091205

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
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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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Abstract

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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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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