Palladium-Catalyzed Stille Cross-Couplings of Sulfonyl Chlorides and Organostannanes
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- 作者：Srinivas Reddy Dubbaka and Pierre Vogel
- 刊名：Journal of the American Chemical Society
- 出版年：2003
- 出版时间：December 17, 2003
- 年：2003
- 卷：125
- 期：50
- 页码：15292 - 15293
- 全文大小：45K
- 年卷期：v.125,no.50(December 17, 2003)
- ISSN：1520-5126
文摘
Arene and phenylmethanesulfonyl chlorides can be cross-coupled with aryl, heteroaryl, and alkenylstannanes with desulfitation in the presence of 10 mol % CuBr·Me2S, 1.5 mol % Pd2dba3, and 5 mol % tri-2-furylphosphine in tetrahydrofuran or toluene under reflux. This extension of the Stille cross-coupling reaction realizes a new and economical method for the generation of C-C bonds. The palladium-catalyzed carbonylative Stille cross-coupling reactions of arenesulfonyl chlorides and organostannanes in the presence of CO (60 bar) at 110 
C in toluene generate the corresponding ketones. Arenesulfonyl chlorides are more reactive than aryl chlorides and aryl bromides in their Stille cross-coupling with organostannanes but less reactive than aryl iodides. The new methods disclosed for the generation of C-C bonds open new possibilities for medicinal chemistry and material sciences.
C in toluene generate the corresponding ketones. Arenesulfonyl chlorides are more reactive than aryl chlorides and aryl bromides in their Stille cross-coupling with organostannanes but less reactive than aryl iodides. The new methods disclosed for the generation of C-C bonds open new possibilities for medicinal chemistry and material sciences.