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- Title
A Highly Efficient and Reusable Palladium(II)/Cationic 2,2'-Bipyridyl-Catalyzed Stille Coupling in Water.
- Authors
Wei-Yi Wu; Ling-Jun Liu,; Fen-Ping Chang; Yu-Lun Cheng; Fu-Yu Tsai
- Abstract
A water-soluble PdCl2(NH3)2/cationic 2,20-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.
- Subjects
PALLADIUM catalysts; CATALYTIC activity; BIPYRIDINE; COUPLING agents (Chemistry); CHEMICAL reagents
- Publication
Molecules, 2016, Vol 21, Issue 9, p1205
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules21091205