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

Autor: Wei-Yi Wu, Ling-Jun Liu, Fen-Ping Chang, Yu-Lun Cheng, Fu-Yu Tsai
Jazyk: angličtina
Rok vydání: 2016
Předmět:
Zdroj: Molecules, Vol 21, Iss 9, p 1205 (2016)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules21091205
Popis: 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.
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